Hiring and Managing Leaders

Hiring great leaders is one of the highest-leverage things you do as a CEO. It’s also one of the most asymmetric. If you get the right leader, the return on the time you spent hiring them can be absurd. Tony Xu (DoorDash) puts it at something like 10,000x. That sounds exaggerated until you remember what a great leader actually does: they multiply the company’s output.

If you get it wrong, it isn’t negative 10,000x, but it can still be very expensive. Tony (DoorDash) estimates it is more like negative 100x. The longer they are in seat, the wider the blast radius. They hire the wrong people, ship the wrong things, break trust, slow down execution, and waste time. So it’s rational to invest a ton of time into the hiring process and to invest in your hiring muscle.

Tony on the asymmetric upside of hiring great leaders

“You think about the returns on time, and if you get the right executive, it could be something like 10,000x. I can't think of a better capital allocation decision on time than that. However, if you get it wrong on an executive, it goes the other way. It might be negative 100x, not just negative 1x. Hopefully, it's not negative 10,000x for anyone on the call, but it's definitely very negative. The upside-downside asymmetry is significant.”

Knowing When to Hire

As a company grows, the most critical role of a CEO is to hire and manage a solid senior leadership team.  The task of recruiting and managing top-tier leaders isn't something CEOs can hand off.  Establishing a strong leadership team is a journey, with continuous improvements required as your company scales.

By the time you reach 30-50 team members, it's time to consider bringing on  leaders. Generally, bringing in external leadership is a necessity once a function becomes repeatable enough to document or, conversely, when it begins to drain your energy and focus from high-leverage tasks.

Below is a framework from Christina (CEO of Vanta) on when to bring in leaders. At around 100–150 employees, Christina realized she could no longer be both CEO and the head of another function. This was the point when she started bringing in external leaders. Her heuristic for when a function is ready for a leader:

• If the work becomes so repetitive that she could “turn her brain off” and do it.
• When a job feels repeatable enough to document in clear steps, the function is mature enough for a leader.

However, you must avoid "shopping while hungry" - hiring out of desperation or organizational pressure leads to poor culture fits and expensive mistakes. To scale effectively, wait until a process is mature enough to hand over, but start your search before the need becomes a crisis so you can hire for quality over speed.

At <100 people, start by hiring “player-coaches” and only when a function has product-market fit.

• Scaled leaders excel at “scaling” functions. Typically, they do not excel at “building” functions from 0 to 1
• Bringing an scaled leader in this 0 to 1 phase is high risk as you’ll lose time and end up having to fix the mess
• In the 0 to 1 phase, own the function and support yourself with player-coaches (80% ICs, 20% managers)
• Once a foundation is in place, look to promote or bring in a player-coach who has high-slope and can scale fast
• Or consider hiring someone with more experience, but is willing and able to operate at the lowest level of detail

Once you have hundreds of employees, true “executives” might become relevant. Key is to find leaders with both experience and the ability to operate at all levels (i.e., in the details). What sets a leader apart is their past expertise in scaling. These experts should be self-sufficient, not needing daily directives.  As time progresses, they should evolve into genuine partners for the CEO, autonomously pursuing set goals that you’ve ideally crafted together.

Building Your Team

Ideally, you're planning leadership hires 6 to 12 (or even 18) months out. It takes many months to find, vet, and close great people. Some functions take longer and will require sifting through more candidates. Planning ahead will give you the best shot at finding the right person and bringing them on before things break down. It will also allow that leader to spend their first few months getting to know the company as opposed to having to put out fires immediately. A good practice is to map out what your company needs to get done in the next 12–18 months, and from there evaluate where the leadership gaps are. Try to develop an intuition for where the bottlenecks are going to be 6, 12,18 months from now. If you're not sure what you need, talk to founders who are a few steps ahead of you. There are general guidelines around which roles you should fill by X stage (see below), but the "right" answer will vary company to company.

1. VP of Engineering

Typically, the first leadership role filled in a startup is the VP of engineering because the engineering team expands rapidly and sourcing engineers is challenging. If your engineering team has grown to 15-20 members and you anticipate further expansion, it's time to consider bringing in a VP. Titles are almost always a point of debate. A tactic some startups have successfully adopted is to offer a "head of" designation for every leadership team hire (like "head of engineering"), postponing firm title decisions and sidestepping title inflation. While this approach can be effective, it's crucial to never lose exceptional leaders over title disputes, especially when their roles are clearly defined. This hire can take 9 to 18 months. Therefore, founders sometimes hire two Engineering Managers (EM) or one Director of Engineering in the interim period.

Beyond engineering, the timeline for hiring leaders can differ. A breakdown for the primary roles:

2. VP of people:

When you should bring on a VP of People hinges on several factors: your employee count, your personal expertise and ease with managing a sizable team, the diversity of your workforce in terms of roles and locations, and any past issues related to personnel.

Generally, we suggest recruiting one or two intermediate HR specialists when your team hits around 50 members, and considering a VP of People when you're between 150-200 employees. It's wise to have someone overseeing administrative tasks like new hire onboarding, office operations, and payroll by the time you're a team of 20. However, a dedicated HR professional can typically be considered as you near the 50-employee mark.

3. VP of sales:

While it might seem appealing to hire a VP of sales early in your revenue-generating phase, it's often not the best move. Initially, it's up to the founders to establish a consistent go-to-market process before passing the responsibility to another.

Top-tier senior sales leaders usually lean towards joining firms where there's a defined product-market fit, and an opportunity to amplify the sales team in response to growing demand. If you're still fine-tuning that fit or your sales approach, it's wise to wait on the VP hire.  Start with some frontline salespeople and a mid-level sales manager. Bringing in a VP of sales prematurely can divert focus from your product and tech teams, e.g. when certain sales deals require engineering effort yet are less relevant to your ideal customer profile. Christina at Vanta only hired a Head of Sales after they hit $15M of ARR. Typically, great sales leaders are good at scaling something that is already working and is repeatable. Until this point, Christina was still figuring out the correct ICP and motion to reliably generate revenue.

4. VP of marketing:

For both B2B and B2C startups, bringing on a VP of marketing or CMO can be challenging, given the broad spectrum of marketing roles. We've noticed that founders often face difficulties securing a top-notch VP of marketing or CMO early on. It's typically more advantageous to recruit someone with in-depth knowledge in a specific area of marketing, such as demand generation or paid user acquisition, instead of seeking a high-level all-rounder. Our suggestion is to initially focus on specialized roles at the director tier and then consider a VP-level position once your marketing team grows beyond 15 members.

5. CFO

Hold off on hiring a CFO too quickly.  A finance director or head of finance can often meet your requirements for an extended period. Typically, our advice is to consider a CFO once your company hits a substantial revenue benchmark (around $50M+) and you're experiencing rapid growth in top-line revenue.

If your business navigates intricate financial waters—say, a fintech firm dealing with multiple financial partners and credit facilities—then prioritizing a CFO might be wise. However, for most scenarios, it's beneficial to postpone this decision until your operations have evolved.  Given the nature of your company, by the time you reach 100 staff members, a finance team of five to six individuals should suffice.

We recommend that your first finance recruit be someone mid-tier with a background in both a Top 4 accounting firm and a startup.  This individual, whether a manager or director, can cultivate a tight-knit team and ideally lead your finance function until there's a need for a CFO.

6. VP of operations

If you run an ops-heavy business (heavy logistics or perhaps a large customer service function), you’ll want an ops leader who has experience in your industry. You do not want this person learning on the job while they’re managing a 200+ person delivery fleet or customer service call center.

7. COO

The COO is often a nice-to-have, and not an essential hire.  Finding a Sheryl Sandberg to directly fill the role of COO at Facebook is extremely rare, and offset by many people like Emily White, an excellent leader who departed Snap after a year as COO.

We believe the best COOs are promoted internally, not hired directly into the job.  The primary reason?  Most effective COOs often have skills and interests that complement those of the CEO. It's challenging to evaluate how well two individuals complement each other without firsthand experience working together. Both Claire Hughes Johnson at Stripe and Lexi Reese at Gusto initially joined as functional vice presidents, such as overseeing sales, and were later promoted to the COO position after demonstrating their capabilities within the company.

If you already have individuals in leadership roles for these functions, it's essential to communicate that they might eventually report to someone more senior. Regardless of how well a lesser experienced person performs, it's typically beneficial to bring more senior leaders into your team over time. While some ICs might rise to executive positions after gaining extensive experience, it's not the norm. For high-potential ICs demonstrating leadership potential, it's crucial to provide them with the right mentors, training, and adequate time to evolve into exceptional leaders. Remember, for every success story, there are likely five who don't make the cut, especially if they're pushed too quickly. Management is a field where experience offers unique advantages.

An exception to this principle: your co-founders. They should be provided with the opportunity to learn while working and have the potential to evolve into long-term leaders. Given their intimate knowledge of the company, akin to yours, they often understand its intricacies better than anyone else.

There may come a time when they recognize that someone else could better perform their role or they might prefer not to manage. In such instances, it's essential to carve out a role that allows them to retain their influence and contribute significantly without the responsibility of managing a vast team. For instance, there was a scenario where a technical co-founder began reporting to a newly appointed VP of Engineering, yet retained his CTO title and remained a pivotal figure in the organization. In another instance, one co-founder managed a product team with 800 employees, while another oversaw engineering until the team reached 150 engineers. After that, they transitioned the role to a VP experienced in managing at that scale.

At Gusto, Josh is the CEO, Tomer London is the CPO, and Eddie Kim is the CTO. Just like Josh, Tomer and Eddie have hired senior leaders with far more experience to work with them on product and engineering. Every founder needs to remember that they will always be the founder, but most execs will only be the VP of X while they are at your company. If there is a way to retain your co-founding team, there are huge benefits. While some of these discussions and transitions can be incredibly hard, we encourage founders to find a way to keep the founding team together as long as they can.

Building and refining a top-tier senior leadership team is a process that spans years. In many ways, it's an ongoing journey.  Thus, it's not unusual to require multiple attempts to establish a resilient team capable of guiding the business to an IPO. Some leaders might excel for a period before reaching their capacity and needing either additional support or replacement. Others might excel but choose to pursue opportunities elsewhere. Some might not meet expectations from the beginning. As a CEO, anticipate that executive recruitment will be a continuous aspect of your role.

8. Chief of Staff

Many founders ponder the need for a chief of staff and their potential responsibilities. It's an individual choice; while some founder-CEOs find value in having one, others manage without. If you're considering this route, here are some guidelines:

A chief of staff should amplify your capacity. Their role isn't merely about managing your calendar or overseeing other staff for you. While some EAs might adopt the chief of staff title, it's distinct from a senior EA position. A chief of staff is more about handling business-related tasks, such as spearheading specific projects or streamlining executive team processes by collating metrics and setting agendas. Ideally, this role is best suited for someone with prior business acumen rather than a novice in the industry.

Avoid emulating a governmental chief of staff model. It's not beneficial to erect a barrier between you and your team, where they feel obligated to liaise through the chief of staff to reach you. Delegating your leadership or filtering information through someone can be a practice in governmental settings, but it's counterproductive in startups. Such an arrangement can decelerate processes and potentially foster discontent among your team.

If you identify a chief of staff model that enhances your efficiency, think about making it a rotational position. Attracting high-caliber individuals for an extended tenure in this role can be challenging. Companies like Amazon have adopted a rotational approach, where adept team members serve a year or two as a chief of staff before transitioning into other roles at the company. 

A few example profiles: Daniel Jabbour (Applied), Ben Gammell (Brex), Asif B. (Replit). These were excellent Chief of Staffs because they all became or will become business leaders of functions.

Hiring Leaders

Recruiting leaders is a distinct process compared to hiring individual contributors. Doing it effectively requires significant time investment. From what we've observed, top-notch CEOs often dedicate over 20 hours to assess and familiarize themselves with potential leadership hires before making offers. Senior candidates tend to excel in interviews; their extensive careers have equipped them with substantial practice, and they've themselves interviewed countless individuals. Consequently, a typical interview might not provide you with much insight. It's crucial to move past the traditional interview framework and attempt to emulate a prolonged working relationship with them. Besides evaluating their professional capabilities, it's equally vital to understand their core values and personal priorities. Here's our recommended approach for executive recruitment:

1. Spend Time with Leaders Told to be Great

Before bringing on a leader for a specific role for the first time, identify and engage with 5-6 top leaders in that domain. When meeting them, be ready to discuss your company and the primary challenges associated with the role. These encounters should not revolve around recruiting; instead, focus on gaining insights, forging relationships that facilitate future discussions, and building your mental model for the role.

Example: Calibration Questions for New Leadership Roles

Understand how they landed their current position:

1. What was their interview experience?
2. What motivated them to join their current company?
3. What challenges did they perceive upon joining?
4. What role did the CEO play in their recruitment process?

Understand the various models and patterns of success and failure within the role. 

1. What are the common reasons for those in their role to fail?
2. How do they measure their success?
3. What is the structure of their organization?
4. What are the vital leadership roles they need to fill?

Inquire about their recommendations for your hiring process: 

1. If they were in your position, what background would they prioritize? 
2. Do they have suggestions for potential recruits? 
3. What are their thoughts on the interview questions you have in mind?

Selecting, establishing rapport with, and recruiting the ideal leader can span months.  Ideally, always keep a running list of the next set of leaders you might need. This foresight not only increases the likelihood of identifying the right individual but also ensures they can join before the function breaks. This proactive approach also gives the new leader a window to familiarize themselves with the company without immediately having to address urgent issues. 

Example: Tactics to Stay Ahead of Leadership Hiring

• Some founders maintain a "future hires" list for every high-level position.  They tap into their contacts and form connections as soon as vacancies are anticipated. At 50-100 employees, Tony Xu (DoorDash) met with 2 leaders a week for 3 years straight. This helped him calibrate what great looks like for roles.
• Some CEOs also maintain a status list for their current leaders. The reality is that not every leader will scale with the company and will either need to be replaced or layered. A few avra founders categorize team members as green for “doing well and scaling”, yellow for “might scale/to watch”, and red for “not going to scale.” For candidates that are categorized as red, start a search. This is an easy way to make sure you are never caught by surprise as great leaders take 6-12 months to hire. 
• Actively expand your pool of potential candidates. Whenever you interact with leaders, regardless of the context, inquire about who they regard as the top professionals in their field. Engage with these recommended individuals and pose the same question to them. Also make sure your current executive team is also leveraging their networks in a similar manner. 
• For B2B companies, two immediate networks to constantly explore are your customers and partners.

2. Decide Whether to look Externally

Don’t forget about internal promotions. 60% of VP+ hires at some companies are from internal growth

• 60% of hires above VP are internal promotions at DoorDash today. Up to 300 people, this was 90%
• Every company is unique in the way they do certain things - internals have context and know how
• With externals, you run the risk of organ rejection. They can’t operate within your company’s interface
• It’s easy to value a lot the shiny object outside of the company versus evaluating the talent within
• Founders framework for <100 FTEs: If someone can scale beyond 1-2 years, give them a chance

Max (CEO, Faire) has a nuanced framework for deciding internal vs external

• How mature is the function: For initial hires who are building out the function, Max finds it helpful to have someone who’s at least operated a couple years ahead of where you want to be, ideally having scaled from your stage to the next level.
  
  • Once a function is built and running smoothly, internal promotion is both easier and preferable. 
• How fast is the function scaling: If the department is scaling quickly, promoting someone too green rarely works.
  
  • For example: Promoting an IC to manager of a rapidly scaling critical function or promoting a junior manager to manager-of-managers in a fast-growing department rarely work because in both cases, the demands outpace the person’s ability to keep up.
• How excellent is the person: There are rare cases where someone is able to keep up without having a world-class leader above them 
  ‍
• Can their manager coach them: Promotions can succeed if the person has a world-class manager who can train and coach them. Pairing an inexperienced leader with an inexperienced manager is especially risky – at least one layer needs to bring deep experience.

How to identify internal talent for promotions? If people are drawn to a person regardless of title - that’s a sign that people respect their opinion/work

3. If Hiring, Establish a Detailed, Documented Vision of the Role

To find the right fit, you must first clearly define the role's expectations. A helpful format to adopt is MOC: mission, outcomes, and competencies. Pinpoint 3-5 key deliverables the candidate should ideally achieve within a set timeframe. We include a sample template below.

Example: Mission-Outcomes-Competencies (MOC)

Template for figuring out what you are looking for when hiring a leader

Mission: Two sentences describing the purpose of the role. Why are you making this hire?

Outcomes: The most important 3–5 results this person needs to deliver. 12 months is a good timeframe. In 12 months, how will you know that this person has been successful? For example:

• Outcome #1: hire and retain a high performing engineering team
• Outcome #2: reduce error rates in software by x%
• Outcome #3: speed up releases by y%

Competencies: The skills and past experience someone needs to accomplish the outcomes. 

Outcome and Competency Examples

Outcome: Hire and retain a high performing engineering team

• Experience hiring at high volume, specifically the ability to recruit top talent
• Track record of retention
• Experience managing performance at a high level‍

Outcome: Reduce error rates by x%

• Experience with root cause analysis and remediation
• Experience reducing error rates
• Experience implementing best practices to ensure less errors going forward

Outcome: Speed up releases by y%

• Experience driving shipping speed

Putting together a solid MOC will help you drill down on what you need out of the role, and ask better questions as you're evaluating candidates. For example:

• Tell me about the best team you've built. Why was it great, how did you find people, and what worked in closing them?
• How have you retained your teams in the past? What was your best retention rate, and what was different from teams who churned?
• Tell me about your approach to performance management. How do you know if your teams are engaged?
• Whatʼs your best example of turning around a low performing team?

4. Consider a Search Firm

Search firms can be helpful when hiring leaders.

The primary advantage of using these firms lies in their efficiency: they consistently expand their executive networks, often specializing by function. Achieving this level of continuous engagement is often challenging for you or your internal team. 

Additionally, these firms can provide valuable insights into outreach strategies and screening methods. Top-tier recruiters maintain enduring relationships with elite candidates, ensuring at least a response to initial outreach.

Many founders are taken aback by the fees of executive search firms, which can range from $90k to $150k, sometimes including equity components. However, those who have successfully partnered with an exceptional search agency and secured a game-changing executive often find the fee justifiable. That said, only a select few search partners are truly worth your investment and time. It's crucial to meticulously assess which ones to engage. 

Best Practices for Selecting a Search Partner:

• Seek recommendations from investors or fellow founders. Aim to get introduced to at least three search partners and arrange meetings with them, preferably within the same week. Provide them with relevant details about your company beforehand. The most competent ones will present potential profiles during the meeting for your feedback.
• Judge based on agility, network depth, and understanding. Unsuccessful engagements with search firms typically arise when the founder must instill urgency, the firm cannot secure introductions to top-tier candidates, or the firm misinterprets the desired candidate profile. Often, it's a mix of these issues. In contrast, some of the best search partners we've encountered meet with every existing executive in the company before initiating the search and are unyielding in their efforts to secure the final candidate.
• Choose an individual, not just a company. Even if Riviera is renowned for engineering searches, it doesn't guarantee that every partner from there will excel.
• Always conduct backchannels on the individual search partner.
• When you begin collaborating, it's vital to swiftly align with the partner. Regardless of their expertise, you possess the most profound understanding of your company and its requirements. Ensure their success by (1) establishing a clear MOC and (2) promptly providing in-depth feedback.

We’ve put together a detailed list of search partners by function here. These partners have all been both recommended by avra founders and vetted by the avra team.

5. Invest ample time in your best candidates

First-time CEOs often find themselves taken aback by the extensive time their seasoned counterparts dedicate to fostering trust and alignment with potential leaders before making a job offer. It's not unusual for CEOs to invest over 20 hours in both formal and informal interactions with candidates. This extensive dialogue serves to gauge the compatibility of the executive with the CEO, the company culture, and the leadership team.

This upfront time commitment not only aids in making a well-informed recruitment decision but also paves the way for a fruitful working relationship once the executive comes onboard. In these discussions, it's pivotal to delve into each other's core values and driving forces, which hold more lasting significance than the day-to-day tasks. Candidness and transparency are key, allowing both parties to genuinely get to know each other. 

For instance, at one startup, the prospective CMO dedicated over 30 hours engaging with the CEO and leadership team during the recruitment phase. At another, the founder and a potential COO invested 40 hours together, which encompassed office hours, hiking, and even introductions to their respective families. Yet another founder prefers extensive weekend calls with potential hires, while another opts to share his recent 360 feedback with candidates, encouraging reciprocity.

Many executive hires falter due to the lack of a robust foundation built on mutual trust and transparency between the CEO and the executive. One particular executive recounted a recruiting process that spanned a mere week and a half. He highlighted the absence of in-depth discussions about core values and principles. The founder, under board pressure to onboard an experienced executive, seemed eager to agree with the candidate without genuine alignment. It's paramount to prioritize authenticity and clarity over merely convincing a candidate to join.

A particularly effective approach to assess a potential executive's fit is to mimic a working relationship. Although it's impractical with a large pool of candidates, when narrowed down to the final choice, it's beneficial to grant them access to the company. This hands-on experience, even before formal hiring, provides invaluable insights into the dynamics of the prospective working relationship, minimizing unexpected challenges and ensuring a smoother transition for the executive once they officially join.

6. Conduct unprompted backchannel reference checks

While soliciting references from candidates is a good beginning, it's essential to reach out to individuals not listed by the candidate.  Throughout this hiring process, aim to create a comprehensive work profile of the candidate, and unsolicited reference checks play a vital role in this. 

The more unbiased feedback you can gather, the better.  It simply provides additional information for your assessment.  However, you should ensure you consult with at least four or five individuals who have collaborated with the candidate over an extended period.

Here are some recommendations for conducting unsolicited reference checks:

• Conduct them personally. While it's acceptable to have others provide a preliminary approval or disapproval early on, when narrowing down to a select few candidates, it's imperative that you delve deeper yourself.
• Tailor your questions to the specific needs of the role. Revisit your Mission, Outcomes, and Competencies (MOC) framework. Probe areas where you're uncertain about the candidate's ability to meet the desired outcomes.
• Always inquire about their hiring proficiency. The quality of your organization hinges on this.
• Accept diverse opinions from references. Leaders can sometimes make unpopular decisions. The aim isn't to verify an impeccable track record but to gather insights on their past situations and their responses to them.
• Jointly Determine the Role and Success Metrics. Since founders often recruit leaders with expertise beyond their own, it's beneficial to cohesively define the specifics and key performance indicators (KPIs) of the role. Engage in these discussions both prior to and post-hiring to ensure mutual clarity and alignment of expectations.
• Even if you're well-versed in the domain, collaborate with the executive when defining the role's nuances. Express your priorities and ensure philosophical alignment, but refrain from micromanaging every aspect. Your dynamic with the executive should epitomize a genuine partnership. For instance, a VP of Engineering at one startup drafted their job responsibilities and KPIs prior to receiving an offer. Upon extending the offer, the CEO made minor adjustments to the executive's proposal, which then formed the cornerstone of their role.

Example: Reference Questions from Alumni Founders

Tactics for reference checks:

• Call a reference and ask them to call you back if they think the person is good.
• Always get context on their working relationship—for example, if you're talking to their former manager, you may not get the best signal on their management.
• Start by asking about strengths because it builds rapport.
• Keep doing backchannels until you find something negative. Everyone has development areas.

Questions to ask:

• “Everyone has development areas. What are theirs?”
• “What were the biggest areas of conflict or disagreement with the team?”
• “What would you expect is on their performance review?”
• “On a scale of 1 to 10, how would you rate them compared to other leaders youʼve worked with in this function? What makes them stronger or weaker? What would it take to get them to a 10?”
• “Who were their peers? Can you rank those people by their relative performance?”
• “Whatʼs your advice for how I can support them as their manager?”
• “What does this person need to succeed? If I bring them into my company, what should I do to make them successful?”
• “In their first 90 days, what are the steps this person took?”
• “Who else should I talk to?”
• “Would you come work with them at [my company]?”

Gather as many anecdotes as possible. Repeatedly asking “tell me more” will help get to truthful answers. Sometimes backchannel references canʼt disclose certain things, so ask, “Is there any reason you wouldnʼt be able to tell me the full extent of your feedback on this candidate?” Before doing references, ask the candidate for the names of their last five managers. Tell them you wonʼt call them without asking their permission first. Then ask, “On a scale of 1 to 10, how would each person rate you? What would it take for that person to get you to a 10?” Since youʼve established that a call may be coming, theyʼre more likely to give an honest answer.  If their answers are vastly different from what their references actually say, itʼs a red flag.

7. Compensation

• Donʼt be cheap. Leaders are expensive. Itʼs one of the more challenging aspects of hiring them. Expect that you'll probably have to break some of your compensation rules to close them. But if you are hiring someone whoʼs going to transform your business, it's absolutely worth it to pay $100,000 more than you had originally intended.
• Use benchmarks. Ask us for comp ranges. Have your board sanity check the candidateʼs numbers.
• Try to figure out the comp equation in their head: How are they thinking about equity? On what time horizon?
• Once you understand this, you can build a comp plan that fits.
• Talk in dollars, not bps.
• Make sure you get what you pay for. Aggressive comp should mean aggressive expectations.

8. Closing a Senior Leader hire

Max Rhodes (Faire) learned from Brian Chesky (Airbnb) that elite founders do not lose candidates. He uses this mindset when closing senior leaders. Below are some tactics and strategies to use when closing:

• Overwhelm them with your enthusiasm for them. Make them feel extremely welcomed and like they could have a huge impact. Say things so effusive that you feel a little uncomfortable. This isnʼt like dating where you risk coming on too strong—you should go over the top.
• Win their family over. Young founders tend to underestimate the influence of a candidateʼs family on their decision. Understand who the stakeholders are in their decision and do what you can to win them over. PeterReinhardt landed Segmentʼs CRO by moving quickly to an offer, sending his wife flowers and chocolate, and offering to fly back to Dublin with the candidate to take him and his wife to dinner. Saji Wickramasekara closed Benchlingʼs CFO by traveling to San Diego to meet the candidate while he was on vacation and had lunch with him and his wife. He also sent a gift basket with Benchling t-shirts that the candidateʼs kids loved.Pedro Franceschi and Henrique Dubugras closed Brexʼs CFO by inviting him and his wife over for dinner and sharing their vision for Brex. They also spoke to the CFOʼs dad to convince him that their ambition was huge.
• Invite them into your company. Have them sit in on all hands and exec team meetings.
• Have them sit in on customer calls. This makes your value prop concrete to the candidate.‍
• Use people in your network. Lean on your investors and others to help close.

Example: Max’s “Bear Hug” Approach to Closing Strong Candidates

• Once down to the top 3–4 finalists, he identifies the highest-potential candidates and spends disproportionate time with them to build trust and mutual connection. The goal is to start the relationship before the hire is in the door so that mutual trust carries into the role
• He uses structured closing steps to make the process deliberate:
  
  • A closing deck late in the process tracking candidate concerns, how they’ll be addressed, and which board members or leaders will reinforce key points. He maps out when each person on the team will meet with the candidate and what exactly each will say

Onboarding Leaders

Outside of hiring the wrong person, the most common reason leadership hires fail is onboarding. Since the upside of getting a leadership hire right is so high and the downside is so potentially catastrophic, onboarding leaders well is one of the best time investments you can make as a founder. Successful onboarding means making five things happen:

1. Maximize chance of success
2. Build trust with the team
3. Build trust with you (the founder)
4. Make sure the person doesn’t screw up the company
5. Quickly identify and take action if it won’t work out

Below we cover how other operators, alumni and avra founders have approached onboarding leaders.

Maximize context transfer during onboarding

A new exec, no matter how senior, arrives with limited to no company context. They don’t yet know what’s weird about your market, what you’ve already tried, which constraints are real, or which problems are actually priorities. So if you want them to make good decisions, you have to treat onboarding as deliberate context transfer, not an opportunity to immediately delegate.

The trap is that the moment they show up, you feel relief. You want to hand them a big chunk of the company so you can go do the other things you’ve been neglecting. Resist the impulse to immediately delegate. These new leaders typically reach for playbooks from their last job, which usually fail because your company is not their last company. Your constraints are different. Your customers are different. And the way you make decisions is different. 

A leader racing to make changes on day 1 without picking up company context is a red flag. Great leaders use their experience, but also think from first principles. If you see a new leader do this, don’t panic. Stay close to the decision and change course if you disagree.

Instead, be deliberate about creating opportunities to transfer context before expecting any changes. As your company scales and there is more surface area, this takes longer and can last 30-60 days. But when you are <100 employees and everything is breaking, that isn’t feasible. Pick a shorter time period (anywhere from a few days to 1-2 weeks) and clearly explain that you want them to learn first. Examples are below.

Examples

Claire (Stripe)

Claire uses a daily 15-minute standup with new leaders. Daily standups are effective because they:

1. Create alignment opportunities before action. Enables execution to start from shared context vs. assumed judgment
2. Answers questions in real time so uncertainty didn’t stall or get resolved incorrectly 
3. Surface early observations, which can be net new insights for you

In a company of 40-100 people, the cadence can taper to 2–3x/week after the first month, but only once context and judgment converge. For larger companies, the period of daily 1-1s can last up to 90 days. The idea is the first 30, 60, 90 days are critical for 1) transferring context, 2) assessing judgement, and 3) aligning on changes to be made.

Vlad (Webflow)

Vlad uses daily 1-1s in the first 90 days (he typically makes ~90%) alongside 1) a written 90-day onboarding plan and 2) a structured 1-1 template. After this 90 day period, Vlad no longer does 1-1s with his leadership team. Instead, he is 1) in constant contact on Slack/other channels and 2) has a weekly office hours slot where direct reports can claim time if they need it.

90 Day Onboarding Plan

• Reading materials to maximize context transfer
• Key people to meet within team
• A high-level overview of goals and outcomes for the first 90 days

1-1 Template and Structure

• Purpose
• Answer questions as they arise
• Align on approach before decisions compound
• Validate whether the exec is framing problems correctly in Webflow’s context
• Meeting Structure
  
  • Vlad uses a structured daily doc to surface gaps in understanding immediately. Doc covers:
    
    • Urgent topics
    • Questions
    • Decisions/FYIs
    • Wins
    • Learnings
    • On deck

Christina (Vanta)

Christina treats the final stage of the interview process as the first context transfer opportunity. She has final-stage candidates work on real company problems using real company data. This is the first opportunity to see how the leader thinks about problems with company context.

Once the leader is hired, Christina accelerates context transfer by preparing a detailed document with the following information:

• How the hire will be communicated to the team
• Who they should meet (and when)
• A breakdown of priorities and how “on fire” each of them are
• A team-level doc with person-by-person notes on strengths, gaps, and unknowns 

The purpose of this document is to offload Christina’s mental model so the new hire doesn’t waste time guessing at Christina’s thoughts. This also helps Christina and the new leader prioritize together, which “fires” or initiatives to pursue over time.

Stay close early on

Manage the new leader closely during the first 90 days. Do not outsource or delegate the function  Best practice

Examples

Grant (Whatnot)

At Whatnot, in the first 30–60 days, Grant continues running the team alongside the new leader rather than fully delegating. In Grant’s mind, every new leader is by default a neutral and not a positive force for the company. They need to prove they can deliver since most will not. Grant’s goal is to validate how they think in Whatnot’s context. Are they solving the right problem? Is the proposed solution grounded in Whatnot’s constraints? Are they copy-pasting playbooks from past companies, or adapting in real time?

During this time, Grant attends every key meeting but lets the new executive lead discussions.  To not bias the team or undermine the leader, Grant only speaks at the end, and spends the majority of the meeting observing how the person frames the problem, applies company context, structures tradeoffs, and articulates solutions.

As part of this, Grant writes a 30/60/90 plan with clear outcomes and learnings, and includes peer and direct reporting chain feedback from high quality people at 60 and 90 days. The goal is to eventually let the leader take reigns without Grant attending every meeting and / or decision point.

Max (Faire)

At Faire, in the first 30–90 days Max manages new execs very closely, then gradually reduces his involvement. His goal is to build tight alignment early and prevent small misses from compounding into larger problems. Max believes starting “micromanaged” and stepping back is healthier than the reverse. Giving too much freedom early and then jumping in later creates a “doom loop,” where the exec feels undercut and mistrusted.

Faire uses starter projects to transfer context and validate a new hire’s capability. Max assigns early projects that force the leader to learn the business and test whether they can actually deliver at Faire. He stays closely involved in these projects early on, and the intensity of his check-ins decrease only toward the end of the 90-day window once the leader’s judgment and execution are proven.

Create opportunities for quick wins and for early evaluation

You don’t want a new leader to make large changes without context or the trust of you and the broader. There are two tools you can use: 1) Quick wins and 2) Start projects. Quick wins are easy wins that help new leaders gain confidence and build trust in the organization. Pick projects they can complete in the first couple of weeks where they have a 90%+ chance of success. Starter Projects are initiatives that give the leader context and validate that they can actually do the job. These are usually completed in the first 90 days.

Examples

Jean-Denis (Plaid) | Quick Win

• Jean-Denis (ex-CTO at Plaid) asked a Head of Design to reformat their Design Review based on team feedback
• He knew he’d succeed because it was broken and wasn’t working for anyone on the 7 person design team 
• He also knew it would build trust as it required the new leader to talk to the whole team and incorporate their feedback

Max (Faire) | Starter Projects

• Max gives leaders starter projects and manages them closely during this period as he builds trust with them (see more here)

Principles for good onboarding

1. Stay very close to the leader in the first 30, 60, 90 days. Gradually step back as context/trust is built
2. Assess how they think, not just what they ultimately decide
3. Expect “playbook” mistakes, but interject and watch how they adapt on the next decision
4. Push company context aggressively to help new leaders adjust quickly
5. Create quick wins for the new leader (helps build team trust and validate the hire)

Firing Leaders

In our experience, leadership hiring is imperfect even with a great process. Depending on who you ask, founders will tell you their hit rate is somewhere between 25% and 75%. So you should assume you’ll sometimes be wrong, and plan for that. Therefore, when you realize a leader isn’t working out, speed matters. The longer they sit in the role, the more surface area they touch, hires they bring in, and decisions they make. Every extra month increases the blast radius, and the amount of effort and time it will take to clean up their mistakes.

Why leaders fail and how to know

• They rely too much on past experience and fail to adapt to the current context.
• They operate at too high an altitude and don’t get into the details. This is widely considered to be the #1 predictor of failure.
• They don’t set a high bar on assessing work quality and instead default to their past experiences, assuming it translates.
• They don’t deeply understand the customer and the product and as a result can’t operate at the lowest level of detail
• They don’t want to grind or are too passive.

How to assess whether a leader is succeeding?

• Is their function hitting goals? If not, is there a clear reason why?
• Are former colleagues following them and performing? Great leaders attract and develop top talent, not just people they’ve worked with before.
• Go to the ground level in their function. For example, if it’s support, go read support tickets—does the work quality meet expectations? If not, the leader is responsible.
• Peer feedback and skip levels with top talent. What is their assessment? Are any top performers a flight risk? Great leaders retain and inspire top talent.
• Coach and give feedback. If these areas aren’t going well, provide direct feedback and an opportunity to improve—this rarely works, but when it does, it’s worth it.

Examples

Whatnot’s Chief Product Officer 

Positive signals at time of hire

• Could articulate in great detail how to build a world-class discovery experience, and they workshopped it for multiple hours. Grant had interviewed 100+ PM leadership candidates by then as this role took the team ~15 months to fill, and asked them all this question since it was our biggest issue at that time.
• Exceptional product judgement that aligned with how Whatnot thought about things, but brought experience in areas Whatnot was weak (e.g., trust)
• Had a big job previously, but hadn’t held it for a long time, so had less anchoring on prior playbooks
• Worked his way up to the job starting as an IC and was still very hungry to prove himself
• Great story teller and leadership qualities that filled known team gaps

Negative signals

• Had a couple backchannels who said they weren’t incredibly strong; some considered him abrasive.
• Whatnot backchanneled those backchannels and found that those leaders were not strong 

How Whatnot knew it would work in the first few months

• Upleveled the PM team in a few months. Brought over an incredibly strong product leader
• Dove in and did IC work to fill gaps
• When he’d copy paste from paste experience, he’d listen to to feedback, and relearn his approach
• Grant attended every product review with him for 2 months, and took note of the decisions he made. Grant would try to remain passive and let him drive, but send him feedback. He very quickly made 90% of the decisions Grant would make, and was better than Grant in a number of areas
• Existing PM team provided overwhelming positive feedback at D60 and D90 (a normally tough group)

When and how to exit leaders

Typically, it's better to fire fast before the blast radius is too wide. That said, you need to balance morale, so use your judgement for when to act. In general, the timeline should be shorter for employees/leaders you expect will cause problems or are extremely disruptive to the company.

Examples

Whatnot

Grant’s approach to deciding when to fire new leaders is the following:

• He tries to not fire too quickly—he believes in giving leaders a three- to six-month window to prove themselves. If the leader isn’t destructive but just ineffective, they are given structured feedback and a chance to improve.
• If they are actively harming execution and team morale, they are asked to leave more quickly. For example, Whatnot fired their VP of X within two months because it was clear they were a poor fit and slowed down execution.

When firing a new leader, Grant takes the following approach:

• A mis-hire is on the company. If an executive doesn’t work out, it reflects a flaw in the hiring process.
• Be fair, but not excessive. Severance should be reasonable and aligned with market norms.
• Give leaders the chance to exit on their own terms. Most senior leaders are given the opportunity to resign rather than be fired. This assumes they aren’t destructive and/or extremely problematic
• Be transparent with the team. Grant ensures his direct reports understand why an executive left to reinforce work expectations.
• A clean break matters. A fair exit minimizes unnecessary tension and protects the company’s reputation in the broader ecosystem.

Vanta

At Vanta, Christina glides leaders out of a role gracefully while still removing them from the company. This involves the following steps:

• Let the leader know it’s not working and this is the end of the road
• Allow them to craft their own exit story with the CEO having veto/approval rights. This can be whatever narrative feels natural to them.
• The speed at which you remove them from the company’s daily operations depends on how disruptive they are:
  
  • If they’re highly disruptive, remove quickly
  • If less urgent, they may stay “in” the company but with no real responsibilities
  • Sometimes keep them on payroll so they can job search while saying they’re still employed. This is typically used for long-term ICs. The bet here is that if you treat your leaders like adults, they will act like adults in return, and that giving people as much control in a situation where they otherwise have very little makes an unpleasant situation slightly easier and helps empathetic managers move faster towards removal

Archetypes of Great Leaders

DoorDash: Tony Xu's Framework for Leadership Hiring

Databricks: Ali Ghodsi's Framework for Leadership Hiring
‍

Case Studies: Hiring

Engineering

Benchling: VP of Engineering

Summary

“We had a different process for the first 6 months of the search but realized we were doing a terrible job because we were letting the team, who were junior and had never worked with a great VPE, do a lot of the assessment. Huge mistake. Our exec recruitment process is completely different now where we know someone is a finalist before they meet the team they are managing, and even then it's a "meet and greet."

In hindsight, I think we lucked into an exceptionally strong recruiter, people leader, and business thinker with Amit. I donʼt need Amit to be the most technical person in the company. I'd encourage any B2B CEO to heavily assess business thinking, which I've observed is weaker in many engineering leaders. I've attached some of the questions I use for every exec search these days. In particular, if a leader (in any role) can't crisply explain the product/go to market of their current company, or I know more than they do from studying it for 30 minutes, that's usually a red flag.

All my best executive hires have grilled me about the business. I felt like I was working at a shitty company coming out of those meetings. I almost wonder if I could hire execs just based on the rigor of questions they ask. I think it is indicative of hiring people who were a stretch at the time and we really had to grow into. Junior candidates try to sell themselves too much and aren't putting the magnifying glass up to the business, which is a turn off for me” - Saji (Cofounder and CEO @ Benchling)

Interview Questions

Topic 1: Set up a scalable EPD organization and process foundations

• Tell me about a large overhaul/restructure of how your team was organized that you've done.
• Tell me about a time when the roadmap processing wasn't working and you had to fix it.
• Tell me about a time when one of your teams wasn't investing enough in infrastructure
• Tell me about a time when your team didn't agree with a process change you wanted to make.

Topic 2: Motivate and develop technical leaders and engineers

• Tell me about an improvement around career growth that you spearheaded at one of your previous companies.
• Have you ever managed a young but talented team before? How did you adjust your style for that situation?
• Have you ever managed a team that felt like the company wasn't valuing their growth enough? How did you handle that situation?
• Tell me about a time when you had to develop a first-time manager.
• Tell me about a time when you lost the trust of a team member and had to gain it back.

Topic 3: Level up the executive team

• When in your career have you felt most accomplished?
• What do you believe accounts for your success?
• What has been your biggest professional challenge or failure? What came of it?
• Is there an area of opportunity youʼd like to address in your next role? How would you approach that development?
• What would you do differently if you were CEO of your previous company?

Topic 4: Create an EPD hiring engine

• Have you ever had to hire without much help from recruiting? How did you go about doing that?
• Tell me about a time when your team wasn't assessing technical skills well and you had to fix it.

Topic 5: Guide engineers who are setting technical direction

• Describe the architecture/high-level breakdown of your current product. How does that translate to your engineering processes, particularly around things like release cycles, testing, tooling? What are some focuses/non-focuses?‍
• Main “technical” question we're asking, checking for depth of understanding‍
• Tell me about a major decision about technology choice/platform that your team recently made that you played a role in guiding.
• What about one where you stepped back?
• Tell me about a time when a team was sacrificing product quality for shipping speed too much and you had to get them to improve this balance.
• Tell me about a disagreement about coding/technical best practices that you had to resolve.

Interview Scoring

All interviewers fill out the STAR framework for each question and rate the response. Here are the guiding questions to help them assess the candidateʼs response.

• Do they seem perceptive/observant about the context around the situation?
• Are they able to boil down the situation to an exact task (goal)?
• Is the action that they took in line with what we'd want them to do in that situation at Benchling?
• Can they link their actions to clear positive (and sometimes negative) results?

Sample Template: STAR Rubric for Sample Question

Question:

Tell me about a time when members of your team disagreed on a process change you wanted to make. What was the disagreement? Why was it happening? What did you do? What was the ultimate outcome?

Response

• Situation: [Describe the situation]
• Task: [Describe the task at hand]
• Action: [Describe the action they took]
• Response: [Describe the outcome]

Scoring

• Perceptiveness about situation: 1, 2, 3, 4
• Boils situation down to the task: 1, 2, 3, 4
• Action aligns with what Benchling wants: 1, 2, 3, 4
• Link results to actions: 1, 2, 3, 4
• Clear communication: 1, 2, 3, 4
• Relevance to question: 1, 2, 3, 4
• Overall: 1, 2, 3, 4

Interview Process

The interview was processed included the following:

• 1 hour coffee with Saji (co-founder/CEO) | this was more sell focused
• 2.5 hours with Ashu (co-founder) | Product demo; covering questions above
• 5.0 hours on site to meet key people
• 1.5 hours with Engineering Managers on topic 1 (scalable engineering) and topic 2 motivating engineers)
• 1.5 hours with Engineering Managers + Josh on topic 5 (guiding engineers) and new problems at Benchling
• 1.0 hour with two engineering folks on topic 5 (guiding engineers)
• 1.0 hour with Saji focusing on how to level up the company as whole
• Debrief as a group to decide if they want to move forward
• 1 hour with board member + dinner with Saji and Ashu (more sell focused)

Faire: VP of Engineering

Summary

Marcelo spent 8 months looking for Faireʼs head of engineering. It didn't go outbound, so there wasnʼt a job posting or req. Instead, Marcelo went deep into his own network. Faire had 13–15 engineers when Marcelo started looking for the head of engineering. They knew they would be growing fast and Marceloʼs calendar was a mess trying to do his job and manage engineers. By the time the head of engineering joined 7–8 months later, the company was at 35 engineers.

Marcelo met with over 65 candidates (many were ex-VPs of engineering at Blackberry with an old-school mentality about engineering since the engineering team for Faire is based in Waterloo). The main realization was that every engineering organization is very different. Marcelo needed to figure out the things that he was good at and should keep vs. the things that he was not as good at or as passionate about.

Marcelo is very technical and wanted to keep responsibility for the vision for technology, scaling their systems, choosing languages, frameworks, tools, etc. He also cared a lot about the people they hired, so he also kept the recruiting function. He needed a head of engineering who was very good at managing people and processes. Someone very data and metrics driven, process oriented and a very good people manager. He didn't care as much about how good the head of engineering was on technology, programming, etc. They ended up hiring Paul Poppert as their head of engineering.

Interview Questions

Think

• What did you see when you came in? What was and wasnʼt working?
• What was the impact of what wasnʼt working?
• Do you think they used you well in this role as it was set up?
• What was your impact on the business?

Execute

• When you took over this role [or started at X company] and you knew what needed to be done, how did you plan your work and your teamʼs work?
• People generally develop rhythms over time of how they plan their work. Whatʼs your rhythm around how you prioritize and manage time?

Lead

• Tell me about the team you inherited. Was it strong? How did you decide who to keep?
• If I were to talk to everyone whoʼs ever worked for you, what would they say they liked about you? What would they wish youʼd change?
• Whatʼs your style as a team leader? How hands-on are you? Do you tend to be nicer or harsher on average as a team leader?
• Do people start with your trust or do they have to prove themselves to you?

Influence

• What kind of people do you find difficult to work with?
• How do you typically show up in a room? Are you the quiet person, do you jump right in, when and why do you decide to chime in?
• Have you had to deal with politics and power dynamics? Howʼd you manage that? How do you handle a political environment?

EQ

• (Create opening by using the context) What should I know about what best motivates you and what pushes your buttons?
• (Create opening by using the role) How do you get buy-in and say no? What personalities are particularly difficult for you to work with?

Sales

Ironclad: VP of Sales

Summary

Jason Boehmig starts the search process for executives far before when the company will actually need them. He met his eventual VP of sales, Damon Miño, when Ironclad had only two or three employees.

Jason knew they'd need a VP of sales at some point and came up with criteria for his dream candidate: someone who had (1) worked at DocuSign or Salesforce, (2) a certain amount of sales experience, (3) a law degree, and (4) worked as in-house counsel (Ironclad's target customer). He found two or three people on LinkedIn that met his criteria and reached out cold to Damon: "I just asked for advice at first. I said, 'We're selling contract software. It's going well but I don't have sales experience and I'm looking for advice from someone who does. Could I get 15 minutes of your time for a call?'"

The call turned into an in-person meeting, where Damon made it clear that he had no interest in joining Ironclad: "Just so you know, I'm happy where I am. What you're doing is interesting and I'm happy to help, but I'm never going to join your company." Jason instead asked him to be an advisor: "I asked if I could pick his brain periodically. We'd meet once a month or quarter for a year. I was half selling him and half asking for advice." After a while, Jason gave him an advisor grant to keep him engaged: "He did really helpful things: giving feedback on our sales deck, helping me think through pricing on a specific deal, helping me come up with the profile for our first sales hire."

As Ironclad gained momentum, Jason was able to get more and more of Damon's attention: "When we first started talking, I was the only salesperson. We hired a great first AE, then more good AEs. Good customers were signing up at a good price point. We had gone from pricing the product at $200 a month to a line of sight into our first six- figure deal."

By the time Jason started a formal VP of sales search—about a year into the relationship—Damon was ready to throw his hat in the ring. But Damon's wife, also a VP of sales, was skeptical, so Jason went over to their apartment and spent an hour pitching and answering questions.

The final step was to put Damon through Ironclad's formal interview process and have him spend time with the team: "Damon and I knew each other well at that point and knew we would work well together, but we wanted to see how the rest of the team would work with him."

Product

Brex: Chief Product Officer

Archetype‍

Pedro distills needs into a simple one liner after meeting with great Product leaders at other companies. For their CPO, Pedro identified the following archetype: An executive that has GM experience (e.g., experience running a P&L and all the functions of a team) and also has product experience.

Initial Meetings

‍Pedro met with 25-30 candidates in the process. Pedro had 1 or 2 initial meetings before passing candidates to meet the broader team and to invest in a working session. During these initial meetings, Pedro goes deep into their past experiences and rarely focuses on hypotheticals. He finds that this is the best way to screen for “the ability to operate at all levels of detail” early in the process. Questions he asked during these meetings:

Background

• Go deep into personal background - where they grew up, why they made decisions, college/school
• What are your product philosophies and principles?
• Why would your X teams not have achieved outcomes without you?
• Go deep into work background - what they accomplished at each role? What did THEY do? Why?

Working Together

• How would we work together? How would our 1-1s, team meetings, product review be?
• How would you feel about me going deep into the product? Engaging with PMs?
• What is your style in running a product? Do you go deep or let teams run with their goals?
• Where are we going to clash? Simulate a disagreement and see how it goes.
• What are your product primitives?
• What do you need help with? What are your weak spots?

Operating at all levels

• Pedro walked through their Enterprise deck and they brainstormed feedback/messaging

Interview Loop & Take-Home

‍For finalist candidates, they set up a series of onsite interviews and working sessions.

Interview Onsite

• 60 minute Meeting with CFO
• 45 minute Meeting with Head of Sales
• 45 minute Meeting with former CPO
• 30 minute Meeting with Chief Legal Officer
• 30 minute Meeting with PM of Middle Market
• 30 minute Meeting with PM of Banking
• 30 minute meeting with PM of Platform
• 30 minute meeting with PM of Growth
• 30 minute meeting with PM of Design
• 30 minute meeting with board member #1
• 30 minute meeting with board member #2

Take home / Working Session:

60 minute working session to discuss positioning of Middle Market and Website. They worked through the deck live and iterated to make improvements on it. Pedro, co-founders, Head of Engineering, Head of Sales, PM of Middle Market, and Chief Marketing Officer were all in the meeting.

References

‍Pedro spoke with ~15 people. After speaking with references, Pedro walked through the feedback with the candidate to deeply understand reasons for each consistent point. Sharing feedback back with candidates is critical as it helps test for humility and self awareness

Webflow: Chief Product Officer

Archetype

‍‍Vlad picks 3 or 4 key priorities to guide candidate identification and focus areas. For CPO, they wanted someone with:

1. Technical background with deep domain expertise in web design and development
2. Track record of leading, hiring, and retaining teams that skew technical and craft oriented
3. Significant experience (or leading as a GM) in commercial growth teams of at least $300M ARR scale
4. Experience with expanding from a single to multi-product company; M&A track record is a big plus 

Initial Meetings

Vlad met with 25-30 candidates in the process. Vlad had 1 or 2 initial meetings before passing candidates to meet the broader team and to invest in a working session. During these initial meetings, Vlad goes deep into their background and tries to align on whether they fit the 3 or 4 key priorities that they outlined. This amounted to the following for Vlad:

• 1 hour with all 25 to 30 candidates to calibrate and see who he wanted go deeper with
• +2-3 hours with 5 to 10 candidates to go deeper on the 3-4 key priorities with Vlad\

Interview Loop & Take-Home‍

For finalist candidates, they set up a series of onsite interviews to test for the criteria that Vlad outlined. Each of the interviewers posted their questions in a shared Google Doc and uploaded feedback directly to Greenhouse so that Vlad could review it. Vlad chose to do this instead of a group discussion, so he could get unbiased feedback.

Onsite #1

• 45 minute Meeting with Vlad on product strategy
• 45 minute Meeting with COO on operational excellence
• 45 minute Meeting with CTO on engineering excellence

Onsite #2

• 45 minute Meeting with CMO on customer and community
• 45 minute Meeting with Director of Product on coaching and development
• 45 minute Meeting with Director of Sales on enterprise sales
• 45 minute Meeting with People leader on leadership and DEI
• 45 minute Meeting with Chief of Staff on alignment and partnership

Onsite #3

• 45 minute Meeting with Vlad on core principles and relationship building
• 45 minute Meeting with co-founder on new product philosophy
• 45 minute Meeting with Head of Product Design on product design
• 45 minute Meeting with co-founder on design philosophy

Take home / Working Session

• Vlad provided an open-ended prompt on expansion from single product to multi-product company. They asked the candidate to prepare their feedback on this topic and to present during a 60 minute working session with the relevant team. Candidates are encouraged to ask for more information. Internal team members are encouraged to treat it like a normal working meeting. The best candidates go above and beyond and prepare detailed presentations or memos on the topic to lead the discussion.

Final Onsite #4

• 60 minute Meeting with Product leadership as a debrief/continued discussion from working session
• 30 minute Meeting with Board Member #1 as close meeting
• 30 minute Meeting with Board Member #2 as a close meeting

References‍

Vlad spoke with ~10 people. During these interviews, his goal is to understand whether what the candidate says is reflected in their actual work. After collecting all feedback, Vlad makes the offer contingent on going through the feedback and identifying areas for development together. Below is his rough interview script.

• Background on working relationship
• [Manager and Peers] What advice would you give me to make this person successful?
• [All] In what areas and skills have you seen [X] grow most significantly when you worked together?
• [All] In your experience, what top words would people use to describe [X’s] management and leadership?
  
  • Dig into words they use to understand details behind each term
• [All] Do you have any examples of when you disagreed on something? How was it handled?
• [Directs] What was it about X that made them a great manager? What is one thing they were better at than anyone else?
• [Technical] Can you think of any examples where [X] demonstrated deep technical or domain expertise?

Interview Questions (Tied Back to Each Topic)

Operational Excellence

• Tell me about a time when you had to manage a complex operational challenge or change management in a previous role.
  
  
  
  • What was the challenge? What steps did you take to address it? What was the outcome?
  • What were the biggest challenges you faced in implementing your solution?
  • How did you overcome those challenges?
• How do you think about investments in product(s) and how they tie back to key financial metrics?
  
  
  
  • Tell me about times you’ve been able to accelerate growth with product strategy.
  • What about driving efficiencies across gross margin or operating margin?
  • How have you reduced churn/contraction with product in the past?
• Tell me about a big bet you made with product strategy. How did that impact the company? What outcomes came of it and given your experience, if you could go back, what might you do differently?
• Tell me about how you think about the organizational structure of your team as the product becomes more complex. How do you partner with your peers to design the org structure and processes to drive velocity and successful product development?
• How do you build your understanding of the customer and their needs? How does this fit into prioritization and your overall product strategy? What are the key groups you work with to build this understanding/empathy?

Engineering Partnership

• What is your strategy to come in and learn a product with the large surface area of Webflow? How do you measure success in learning the product? How do you set strategic product direction while coming up to speed?
• How do you measure product velocity? Can you give an example where you had to change the velocity of a product (faster or slower) and what was the outcome?
• When building product strategy, are you data-driven or data-informed or do you use other input? What is an example where this helped in building your product strategy?
• What are the traits of the best engineering leader that you have worked with in the past? How did those traits manifest themselves in the working relationship between you and engineering? Conversely, what was the worst working relationship you had with an engineering partner? What steps did you take to rectify the relationship and what was the outcome?
• There is the classic choice when building a product: time, features, quality, pick two. Which two do you pick? Can you give an example of a time when you struggled with this decision and what was the outcome for the product? Have you ever sacrificed quality for features?
• What is your strategy to earn the trust of your new directs and your other EPD peers? How do you measure this trust?
• What feedback do you want to receive from your EPD peers? How often would you like to receive feedback and how do you take action from this feedback?

Coaching & Talent Development

• Tell me about your approach to people leadership. What are some common tools or practices you find yourself leaning on because they’ve been really effective for you?
• How do you think about career development and coaching for your direct reports? And how does that change as companies reach Webflow’s scale and beyond?
• Can you give an example or two of senior leaders on your team who you’ve helped reach the next level?
• Can you give an example of where that wasn’t successful?
• How do you approach performance management? And can you give me an example of a challenging situation you had to work through?
• How do you balance setting direction, maintaining product integrity, and empowering your leaders? Can you give an example of where that’s gone well and an example where that didn’t go so well?
• Thinking beyond just your direct reports, can you talk about how you’ve incorporated talent development or learning & development as a key priority for your whole org?

Customer Empathy

• How do you think about balancing multiple different personas in developing a product? How important is singular ICP focus versus not for a company like ours?
• How do you ensure deep customer insight and empathy is infused in how you develop products?
• Pricing & Packaging: How do you think about bridging what you’ve built with how we take them to market, particularly from a P&P perspective?
• As we shift our company from our historical focus on freelancers and small agencies to larger In-House Teams, how do you think about balancing investments across potentially competing segments?

Enterprise and Sales Partnerships

• Which product launch that you’ve led has most impacted top-line revenue? Lessons learned?
• “Voice of Customer”: Can you share an example of how you’ve captured prospect/customer feedback?
• Webflow competes in a mature industry: Web development/CMS/DXP. What steps would you take to create a framework for how we will win this market from a product perspective?
• PLG levers: Can you share an example of working with Sales Leadership on In-Product triggers for moving customers up through PLG offerings (upgrading from Free / Self-Serve)?
• What are the traits of the best sales leader that you have worked with in the past? How did those traits manifest themselves in the working relationship?
• Conversely, what was the worst working relationship you had with a sales partner? What steps did you take to rectify the relationship and what was the outcome?
• Example of a disagreement Product ↔ Sales on a specific feature/product prioritization? What happened & resolution?

Whatnot: Chief Product Officer

Model Companies

• Stripe, Airbnb, Doordash ‍
• Could be interesting (but no knowledge of product talent/culture): Coupang, Shopify, Bytedance (non-US)

Mission:

• Consistently deliver a product users love fast that moves the business forward

Outcomes (18 months):

• Build a world-class product team‍
  
  • Grow product team from ~5 to over 20+ world-class product managers with strong product sense, amazing executional ability, and strong XFN skills
  • Build a user-first product culture aligned to Whatnot’s principles
  • Ensure everyone on the team is an avid user of the product and deeply understands all core components of the business

• Deliver a product that user’s love and achieves our business goals fast‍
  
  • Ensure the product supports and helps unlocks $700M/mo in GMV sales
  • Ensure Whatnot is a trusted brand amongst buyers and seller
  • Deliver a world-class discovery product that ensures buyers find and discover things they’ll love
  • Generate over $100M+/mo in async sales on Whatnot

• Build the best XFN product team‍
  
  • Ensure the entire XFN product team is the top-executing team amongst growth-stage companies
  • Develop strong roadmaps and team visions & strategies for product pods that enable us to hit upon our business goals faster & build better products for our users

• Ensure Whatnot is capable of quickly and effectively launch into all core verticals and countries‍
  
  • Ensure the Whatnot product and team is capable of launching a compelling product in all core verticals we want to enter (Collectibles, Cars, Food & Beverage, Home & Garden, Fashion, Electronics, Healthy, Art, Crafts, and Beauty & Digital)
  • Enable $10M+/mo in sales in 5+ product verticals
  • Drive $100M/mo in sales from outside the US

• Drive sustainable growth through Whatnot’s product‍
  
  • Help develop sustainable growth channels that consistently drive 60%+ of Whatnot’s growth (sharing, SEO, referral and more)
  • Ensure Whatnot’s channels and funnel are optimized to drive strong growth

Competencies

Top 5

• Team-builder: Is adept at judging talent both for skill and cultural fit. Has built exceptionally strong product teams in the past that have executed and delivered strong product roadmaps quickly
• Strong product instincts: Can step outside of the numbers to understand what makes a great product for users, and think the product pieces need to bring this to live
• Great executer: Can cut through the noise, make swift decisions, and ensure the team is set to deliver on their roadmap with few missteps. Can do this in the product team and amongst XFN stakeholders
• Has seen a best-in-class company scale from a ~200 people to 1k+ in a product role with significant scope
• Has worked in multiple different roles and environments, so doesn’t just default to previous way of solving a problem

Qualities (In order of importance)

• Exhibits characteristics of Whatnot’s culture
• Team-builder: Is adept at judging talent both for skill and cultural fit. Has built exceptionally strong product teams in the past that have executed and delivered strong product roadmaps quickly
• Strong product instincts: Can step outside of the numbers to understand what makes a great product for users, and think the product pieces need to bring this to live
• Great executer: Can cut through the noise, make swift decisions, and ensure the team is set to deliver on their roadmap with few missteps. Can do this in the product team and amongst XFN stakeholders
• Oriented towards speed vs. perfection: Knows that great software is made iteratively, and not through perfection. Comfortable shipping MVPs, and moving quickly to make them better
• Exceptional communicator: Can easily communicate complex ideas, and align XFN teams on the roadmap and work we must achieve to bring the company forward
• Highly analytical: Incredibly analytical. Easily able to gain mastery of the core elements that drive a business, and has a command of business metrics than rivals anyone within any organization
• Great partner: Can easily with with a large number of XFN stakeholders and bring teams together to produce incredible outputs
• Strategic: Understands how to invest in the product and roadmap give a business increased advantage over time
• Risk taker: Willing to comfortably make bets that could change the trajectory of our business

Previous Experience (In order of importance):

• Has worked in multiple different roles and environments, so doesn’t just default to previous way of solving a problem
• Has seen a best-in-class company scale from a ~200 people to 1k+ in a product role with significant scope
• Has managed a PM team of 20+
• Has worked in an eng-first organization
• Has built successful 0-1 products in the past (ideally, as a founder)
• Has experience in a marketplace business

Finance

What to look for in your first Head of Finance hire?

While a Head of Finance will need to be able to handle financial operations (e.g., AP/AR) and accounting, we recommend focusing on candidates that excel at the forward-looking components of Finance, which includes planning, capital allocation, and strategic decision making (e.g., How much should our team invest in this GTM partnership). In short, you want a Head of Finance that will accelerate your decision making and help you and the team make better decisions about how to continually improve the business. These skills also translate to fundraising when you need to paint a future narrative for the business.

We have found that the best Head of Finance candidates have the following characteristics:

Experience

• Investment banking or consulting, plus
• Growth equity or private equity, plus
• Strategic Finance or Biz Ops at a high-growth startup

This background combines a solid foundation of technical training (e.g., traditional corporate finance) with the operational lens required to work within high-growth startups. For your first finance hire, cautiously approach candidates that have never worked in startups before as these candidates are usually well versed in analysis, but do not have the experience working cross functionally to create and operationalize a plan. Don’t veto this type of candidate, but test for characteristics that align closely to working in startups (e.g., comfortable with uncertainty and the other characteristics below).

You will notice we don’t mention experience in your specific business model. In our experience, great finance leaders can learn business models. They are experts in dissecting a businesses P&L and coming up with key drivers and inputs. The exception to this rule is financial services where finance leaders need experience in capital markets and credit management. Below is a quote from Michael Tannenbaum, COO & CFO at Brex, on why you shouldn’t use business model experience as a hard constraint.

“It [SaaS] can be learned. Hard to get someone w good I-banking / consulting experience + moved into tech + management, so narrowing to SaaS feels unnecessary as in my opinion SaaS is simpler than fintech for sure and probably even marketplace given the financial operations of those businesses”

Qualities

• People oriented as they will work across teams to devise plans and will interface with investors
• Process oriented as they will need to own cross-functional planning at the company
• Comfortable using data to frame decisions as they will need to help non-finance roles make decisions
• Comfortable with uncertainty as they will support teams to answer open-ended questions 
• First-principles thinker as they will help you devise activity metrics to run the company
• Detail-oriented as they will be a key stakeholder in planning. You need accuracy and 
• Curious as they will need to ask questions to support other functions within the company
• No Ego as the first Head of Finance will need to wear multiple hats to get the function running
• Willing to challenge the CEO and other leaders as they will need to hold other teams accountable

First Head of Finance Examples

‍

Hired Andy Toung at 25 People and ~$1M ARR

• Experience: Banking, PE associate at Silverlake, and Founder/Chief of Staff
• 9 years of total experience prior to joining Gusto
• Silverlake is an “operationally” focused PE firm; great training for planning
• Founder role prepared Andy to operationalize his PE work and wear multiple hats
• Started as a Head of Finance, but wore many hats early on. Andy helped build the legal, office operations, and people function initially. Over time, leaders were hired for each of these roles. Andy is now the Chief Strategy Officer at Gusto

‍

‍

Hired Zach Grannis at 30-40 people 

• Experience: Banking, PE investing at CircleUp partners
• 8 - 9 years of total experience prior to joining Faire
• Strong technical background from banking and investing in PE at CircleUp
• Faire hired a CFO 15 months later, but Zach still leads Finance & Strategy

‍

‍

Hired Ryan Colburn at 100 to 150 people and >$200M of GMV run-rate

• Experience: Analytics at Wayfair, Army Service, Strategic Finance at Blend
• 6 - 7 years of total experience prior to joining Whatnot
• Strong background in planning and strategic analysis (e.g., pricing analytics)
• Whatnot was in hyper growth. They needed someone to formalize planning and build out the function before they hired a CFO. Brought in a CFO 12 months later
• Ryan runs FP&A, International, and Financial Systems and reports to the CFO

It’s important to note that the first Head of Finance for most companies does not scale to the CFO. They will usually lead the function and build out the initial foundations before a CFO is brought into the company.

Case Studies: Onboarding

Note: In the early stages of growth, it’s unrealistic to assume a leader doesn’t start executing until day 90. Adjust the onboarding plan accordingly. The key is to stay close early and to sufficiently transfer context. Below are a series of examples for avra and alumni companies at scale >300 EE.

Webflow (~700 employees)

Top of Mind Priorities

Agenda for 1-1

• Product and Strategy
  
  • Deeper dive into 3-year strategy
• Product organization
  
  • Current organizational structure
  • X interim transition
  • Taking ownership of product rituals
• Team
  
  • [Go through each of leaders]
• Partnerships
  
  • [Go through partnerships with cross-functional teams]

Important Reading

• Webflow 2.0 Mission and Core Behaviors - cornerstone of culture at Webflow
• 3-year Product Strategy Video
• FY25 planning and OKRs
  
  • OKR 1: X
  • OKR 2: X
  • OKR 3: X
  • OKR 4: X
  • EPD FY25 Plan
  • Marketing FY25 Plan
  • Sales FY25 Plan
• Watch Bret Victor's "Inventing on Principle", which inspired me [Vlad] to work on Webflow in 2012
• Read "Investing on Principle" - a social contract signed with all investors
• 2023 Board Meeting Notes
  
  • Q423
  • Q124
  • Q224
  • Q324
• Read latest metrics decks

Important Reading (EPD Specific)

• New EPD Structure
• EPD FY25 Headcount
• EPD Budget

90 Day Plan

Week 1

• Complete Workday tasks
• Meet with People partner to discuss team, strengths, challenges
• Meet with X, your onboarding mentor, to better understand culture
• Start meeting with exec colleagues to discuss how teams collaborate
• Start meeting with Product and Design leaders. Attend Product meetings

Month 1

• Finish general onboarding
• Participate in New Leader Assimilation Process
  
  • This is mean to highlight key questions, concerns, assumptions held by your team
• Get introduced to key stakeholder groups in Q4 Manager Meeting
• By end of month, schedule a half day working session with Vlad
  
  • Share a retroactive on first month of learning
  • Co-work on shared/mutual expectations
  • Co-work on high-level goals for product team

Month 2

• Participate in immersive experiences to familiarize yourself with different areas of the company
• Meet with People Partner to discuss bottom's up approach to org design

Month 3

• People Partner will conduct a 360 with your direct reports to give you feedback on progress so far
• Share a draft vision/strategy/plan with Vlad. Bias towards forming a structured plan you believe in vs. jumping into initiatives
• Schedule a focused check-in with Vlad on goals, progress, and expectations
• Share any org change recommendations

Recommended Meetings

• Key Partners (1 hour)
  
  • CTO
  • COO
  • People Partner
  • Product Operations Manager
  • Co-Founder
  • Chief of Staff
  • EA

• EPD Leaders (1 hour)
  
  • Co-Founder
  • Director, Product
  • Director, Product x2
  • Director, Product Design
  • Director, Insights
  • Senior Group PM
  • Senior Product Designer

• Partnership (1 hour)
  
  • SVP Sales
  • Director, Product Marketing
  • CMO
  • Director, Business Operations
  • VP People
  • VP Growth
  • Director, Talent
  • Director, Corporate Development

• Other
  
  • Long list of other important people

Faire (~1000 employees)

How Max Onboards and Manages New leaders in the First 90 Days

• Early on (first 30–90 days):
  
  • Max manages new executive hires very closely at the start, then gradually steps back.
  • This helps new leaders build alignment quickly and prevents small misses from compounding into bigger problems.
  • He believes it’s better to begin with micromanagement and reduce it over time. Giving too much freedom early, then jumping in to correct creates a “doom loop” where the exec feels undercut and mistrusted.

• Weekly structure:
  
  • Holds weekly 1:1s with the new exec.
  • Runs skip-level meetings with their direct reports.
  • Requires a 30/60/90 day plan and tracks progress against it.
  • This structure ensures visibility into priorities, alignment, and execution from the very beginning.

• Starter projects:
  
  • Assigns projects that both give the exec context and validate that they can actually do the job.
  • Manages them closely through these initial projects, only reducing intensity of check-ins towards the end of the 90-day window.

• Feedback:
  
  • At the 90-day mark, runs a start–stop–continue exercise with the exec’s direct reports and cross-functional peers.
  • Ensures the exec is on the right track.
  • Also builds the habit of receiving structured feedback early in their tenure.

• Hold pre-360s at the outset:
  
  • Shares his own expectations of the hire’s strengths and growth areas going in.
  • Establishes a feedback culture from day one, which makes future feedback less awkward and more actionable.

• End of the 90 days:
  
  • Sometimes someone on the team may feel like they’re “managing” the CEO. Max sees this as often helpful (especially for more junior founders) because it provides added perspective and balance
  • By the end of the process, the goal is for the exec to be fully aligned with the company’s priorities, have a track record of validated performance, and be accustomed to continuous feedback loops.

Jean-Denis Greze (Plaid)

Here is an example of a 30/60/90 day onboarding plan for a VP of Engineering from Jean-Denis, the former CTO of Plaid. 

‍Summary Structure

30/60/90 days

• 30 days: Meet people on the team
• 60 days: First quick win
• 90 days: Give feedback, deliver second quick win

3 months

• 3 months: Perform their first medium fix

6-9 months

• 6-9 months: Evaluate their fit
• This is another escape hatch

12 months

• Evaluate some of the bigger things they have done

Goals

• Get to know people
  
  • Within 45 days, meet everyone in engineering
  • Within 120 days, meet everyone in the company

• Deeply understand the technical stack
  
  • Frontend
  • Backend
  • Infra
  • Security
  • Data / analytics
  • Operational aspects, including incidents

• Deeply understand major technical & product flows

• Deeply understand existing Engineering interfaces with
  
  • Recruiting
  • Sales + Business Development
  • Operations
  • Support
  • Finance
  • Legal
  • Data
  • Design
  • Growth + Marketing

• Deeply understand the business
  
  • Product & technical roadmap
  • Finance models
  • Sales numbers
  • Exec docs
  • NPS
  • Plan

Weekly Plan‍

Week 1

• Join email lists , TODO lists, slack channels
• 1-1s with 5 new people in Engineering
• 1-1s with rest of exec team
• 1-1s with Recruiting team
• Go over recruiting process & pipeline stats
• Read postmortems from last 6 months
• Write “Working with me doc”
• Go through customer sign-up flow (or any of the high-level product flows) and the related pieces (including design docs)
• Set up builds and deploys from laptop
• Have at least one commit merged / deployed
• Determine recruiting workflow with Head of Recruiting for each Eng team
• Start attending recurring meetings, Exec meeting, Engineering cross-functional (i.e. engineering leaders),
• Project/product meetings, etc.

Week 2

• Learn production topology (1-2 days)
• Embed with Infra team (2-3 days)
• Add a new feature/metric to Looker
• 1-1s with 5 new people in Engineering
• 1-1s with 5 new people outside of Engineering
• Start shadowing phone screenings and on-sites
• Shadow Cofounders 1-1s with engineers
• Get up to speed with roadmaps (product + engineering, business)
• Work with Recruiting on Salary bands and attend recruiting sourcing meetings

Week 3

• Read last 2 quarterly reports and previous board meeting materials
• Read Sales docs
• Read Finance docs
• Understand assumptions and build ups for 2018 financial model
• Week 4
• Draft interviewing framework
• Review and update engineering JDs
• Read SOPs for Ops
• Read ~3 support tickets from each category for the last 2 months

Week 5

• Start participating in interviews
• Embed with core teams and review
• 1-1s with 5 new people in Engineering
• 1-1s with 5 new people outside of Engineering
• Schedule 1-1s with direct reports
• Write 1-month observations

Month 2

• Direct reports handoffs from cofounder
• Review top products we need integration with
• Embed with new product team (2-3 days)
• Finish meeting everyone on engineering
• Continue meeting ~5 new people outside of Engineering per week
• Write Q1 personal goals
• Meet ~5 companies upmarket which are underserved by existing product
• Embed with Support & Operations (1-2 days each)
• Write Engineering Manager Expectations doc
• At least 5 people from my network interviewing at the current company
• Select mentors for Internship program

Month 3

• Finish meeting everyone in the company
• Write 90-day observations
• Draft Q2 goals for Engineering
• Talent review for Engineering
• At least one person from my network joining the company
• Handoff closing process for all engineering hires from Cofounder
• Social event for Engineering

Gusto (~4000 employees)

Onboarding

• Week 1-2: Orientation and Introduction
  
  • Day 1-3: Welcome meeting with CEO
    
    • Review role charter, responsibilities, and authority
    • Introduce company vision, mission, and values
    • Tour of office and introduction to immediate team
    • Set up necessary accounts and tools
  • Day 4-5: One-on-one meetings with each sales team member
    
    • Introduction to key stakeholders (e.g., Product, Marketing, Customer Success leads)
    • Review current sales processes, pipeline, and CRM

• Week 2: Deep dive into current sales strategy and performance metrics
  
  • Review of top accounts and ongoing deals
  • Begin shadowing sales calls and meetings

• Weeks 3-4: Deep Dive and Assessment
  
  • Conduct a thorough analysis of current sales operations
  • Review historical performance data and identify trends
  • Meet with cross-functional teams to understand product roadmap and marketing strategies
  • Attend customer meetings to gain firsthand insight into customer needs and pain points
  • Begin formulating initial observations and potential areas for improvement

• Weeks 5-8: Strategy Development and Team Building
  
  • Develop a preliminary sales strategy based on initial observations
  • Hold a team offsite to build rapport and gather input from the sales team
  • Begin implementing any quick wins identified in the assessment phase
  • Start one-on-one coaching sessions with team members
  • Establish regular team meetings and communication rhythms

• Weeks 9-12: Execution and Refinement
  
  • Finalize and present a comprehensive sales strategy to CEO and leadership team
  • Begin implementing new processes or strategies
  • Conduct first round of performance check-ins with team members
  • Start contributing to revenue forecasting and pipeline management
  • Identify key metrics for ongoing performance tracking

• Throughout the 90 days: 
  
  • Weekly check-ins with CEO to discuss progress, challenges, and alignment
  • Regular updates to the sales team on observations, plans, and changes
  • Feedback sessions with team members and key stakeholders
  • Documentation of learnings, decisions, and plans for future reference

• End of 90 Days: 
  
  • Comprehensive review meeting with CEO
  • Presentation to leadership team on state of sales org, strategy, and future plans
  • Team meeting to reflect on the first 90 days and align on go-forward plan

Throughout the onboarding process, Gusto uses a Role Charter to communicate responsibilities while onboarding. These role charters become a system you can use to hold your directs accountable. They clarify expectations and leave no room for interpretation. A role charter includes the following information: 

• Purpose - The reason the role exists
• Accountabilities - Qualitative expectations for the role
• Parameters for Success - Quantitative metrics they will be held accountable for
• Key capabilities and behaviors - Behavioral norms and expectations
• Decision rights - Where do they own the decision versus the CEO/others

Here is an example Role Charter Gusto used while onboarding a sales leader:

• Responsibilities:
  
  • Sales Strategy and Execution
    
    • Develop and implement comprehensive sales strategies aligned with company goals
    • Establish and optimize sales processes and methodologies
    • Set and communicate clear sales targets for the team
  • Pipeline Management
    
    • Oversee and optimize the sales pipeline
    • Implement and maintain a robust CRM system
    • Ensure accurate and timely reporting of sales activities and forecasts
  • Customer Relationships
    
    • Build and maintain relationships with key accounts
    • Oversee customer success initiatives to ensure high retention rates
    • Gather and act on customer feedback to improve products and services
  • Revenue Forecasting
    
    • Develop accurate sales forecasts
    • Analyze sales data to identify trends and opportunities
    • Provide regular updates to leadership on sales performance and projections
  • Team Leadership and Development
    
    • Recruit, train, and mentor sales team members
    • Conduct regular performance reviews and provide ongoing feedback
    • Foster a culture of high performance and continuous improvement

• Key Performance Indicators (KPIs):
  
  • Sales Revenue: Meet or exceed quarterly and annual revenue targets
  • Conversion Rate: Improve lead-to-customer conversion rates
  • Average Deal Size: Increase the average value of closed deals
  • Sales Cycle Length: Reduce the average time from lead to closed deal

• Decision-Making Authority:
  
  • Full authority over sales team hiring, firing, and performance management
  • Autonomy in developing and implementing sales strategies
  • Authority to negotiate deals within predefined parameters
  • Input into product development and pricing strategies

• Reporting Structure:
  
  • Reports directly to the CEO
  • Direct reports include all sales team members (until further structure is developed)

Shishir Mehrotra (Coda)

Here is a template of an 8 week generalized executive onboarding plan from Shishir, former CEO of Coda

Here is a helpful template that Shishir Mehrotra (co-founder and CEO of Coda) uses to onboard leaders. Similarly, it defines a specific plan and sets expected outcomes for the incoming executive to be successful.

Case Studies: EA

Wade Foster (Zapier)

Provided by Wade Foster, CEO of Zapier

Whether you're new to working with an EA or have prior experience, this guide should help establish a productive partnership and give guidance on leveraging the expertise of your EA effectively. Let's dive in!

The EA Role

The EA role is valuable for freeing up exec time for more strategic and high-leverage work. Familiarizing yourself with the typical responsibilities of executive assistants can help you better utilize their skills and expertise.

The jobs to be done fit into a few main categories:

1: Task delegation of work that a CEO would normally do themselves

EAs give CEO’s time back to the business. CEOs identify tasks that they would normally need to do but can be efficiently handled by their EA and delegate them accordingly. CEOs should delegate things that are on their to-do list but they uniquely do not have to do in order to free up their time for higher leverage work. Once partnership is established, the EA will naturally be able to know where to lean in. Tasks include:

• Own and optimize to-do list and prioritization. Keep CEOs focused on priorities on a daily, monthly, quarterly basis. Remove distractions, ensuring focus on the key drivers of the company’s success.
• Master CEO’s calendar with great attention to detail. Coordinate internal and external meetings, interviews, all hands, etc. Evaluate their time management and strategize on how to best spend their time. Find alternative representation or decline meetings when the CEO doesn’t uniquely need to attend. Evaluate when meetings can be moved to async.
• Assist CEO with their meeting preparation and presentations
  
  • Lead internal communications: Own our company-wide weekly all hands, run our internal podcast, write a weekly memo for Wade, write his retreat keynote, choose programming for things like Director's Huddles or other leadership meetings
  • Own the company calendar: work with teams across the entire org to choose dates for all of our company activities (planning cycles, performance reviews, annual user conference, big launch moments, retreat/offsite dates, etc.)
  • Project manage ad hoc company projects (ex. our restructuring) 
  • Run Wade's social media
  • Attend all of his meetings. This is how I get the info I need to act as Wade's "second brain"
  • Run exec hiring processes partnering with external recruiting firms
  • Establish rituals and norms across the company
• Communicate internally and externally on behalf of the CEO, helping triage inbound requests or drafting correspondence (email, Slack, HQ posts, etc.).
• Coordinate all travel arrangements
• Handle all expense reimbursement
• Use AI and automation and suggest new systems/technologies to increase efficiency and productivity for you and your exec(s), creating better efficiencies of information flow
• Assist with personal tasks/scheduling
• Acting as a bridge between the CEO and other departments (DIBE, comms, events, recruiting, L&D, etc.), ensuring clear and effective communication. Triage requests from others in the org.
• Gather, organize, and maintain relevant information and documents for the exec's reference.

In order to do this well, CEOs should share preferences and priorities openly with their EA. The more your EA knows, the more productive both teammates can be and the better an EA can complete tasks to the CEO's satisfaction. The style of feedback you give an EA will feel different than other direct reports or peers.

• Examples of preferences to share: restaurants for external meetings, email tone and formatting, times of day for getting maximum focus, how/when to reach you on vacation, what communication channels you like

2: Support the CEO <> direct report relationships

• Work with recruiting to improve the candidate experience when CEO is hiring for a role on their leadership team
• Onboard new direct reports to the exec’s leadership team
• Leadership team meeting support: help CEO prep most important topics, draft cascading comms
• Keep a pulse on morale. Identify and escalate issues to the exec's attention.
• Offer guidance and feedback to CEO’s direct reports on how to work effectively with their CEO. This could include sharing tips for preparing for meetings, providing insights into their priorities, and offering suggestions around their working style.
• Streamline and execute logistics of team operating system
• Work with L&D to organize team building sessions like Birkmans or leadership sessions at retreats

3: Give opinions/input/feedback to CEO on a variety of topics

• Executive Assistants possess a wealth of knowledge and have a unique perspective due to the level of visibility they have in the org. Actively seek their opinions and ideas on projects to benefit from their expertise and support you in making informed decisions. Keep in mind this role is focused on breadth across the company/function, not depth on a particular topic/bet.
• When the partnership has been established, CEOs can consider having their EA participate in strategic meetings to provide valuable insights and contribute to decision-making. Or allowing them to preview docs etc. and have their EA raise when they spot gaps in decision-making.
• EAs can advise others in the org on how their CEO makes decisions to support improvements in work before their review
• EAs also give feedback to their CEO to help them improve as a leader

4: Contribute to leadership team culture

• Support Events & Experiences in the logistical and team-building aspects of planning team retreats
• Depending on the function, EAs may organize things like welcome coffee meetings for new hires, monthly social hangouts, watercooler topics, etc.

Differences between our EAs at Zapier

Executive Assistant

This role is focused on completing a broad variety of administrative tasks for multiple executives at a time, and is limited in depth. Expect the majority of work to fall under category #1, but it depends on bandwidth.

Executive Business Partner

This role is a long-term strategic partnership that has a broader scope of anything needed to help the CEO be successful, although the work streams outlined above are still the priority and other work is limited by bandwidth.

Manager, Executive Assistants

This role is similar to the Executive Assistant role, but given management responsibilities it reduces the bandwidth for directly supporting exec(s). Additional responsibilities include:

• Manage the Executive Assistant function: Including driving job competencies, performance evaluation/management, and learning/development.
• Support execs across the company with tips/feedback on how they can best utilize their EA, and by offering guidance on specific scenarios. Will check in with execs quarterly on Executive Assistant’s performance.
• Keep a pulse on EA bandwidth and help the team with ruthless prioritization and upwards communication on priorities to execs.  

The Introductory Meeting

An intro/kick-off meeting can establish rapport and lay the foundation for a successful working relationship. Open lines of communication from the beginning will foster a strong connection.

• Introduce yourself, sharing your background, and discuss your goals and priorities as a CEO.
• Inquire about your EA’s relevant experience and areas of expertise.
• Openly answer a variety of questions from your EA that will help them onboard into their role.
• Establish expectations for regular check-ins to discuss ongoing projects, priorities, and updates.

Teaching Priorities/Preferences/Expectations

Share your preferences and priorities openly with your EA. The more your EA knows, the more productive you both can be and the better they can complete tasks to your satisfaction.

• This could range from your preferred restaurants for external meetings to specific email formatting to the times of day you can get maximum focus.
• Communicate your preferred communication channels.

• Have detailed discussions with your EA to clearly define your expectations, priorities, and preferred working style.
• The style of feedback you give an EA will feel different than other direct reports or peers.

Providing Necessary Info/Resources

Ensure your EA has access to the information and resources required to carry out their tasks effectively.

• Share relevant documents and contact information.
• Provide necessary access permissions to systems and tools.
• Share background information that can help them understand the context of their work and contribute to their effectiveness.

Task Delegation

• You cannot scale without getting good at delegation. EAs are a force multiplier so you can get more done. They can scale your time so you are a more effective exec focusing on where you can provide meaningful value to the company.
• Identify tasks that can be efficiently handled by your EA and delegate them accordingly. If you are new to working with an EA it can feel unnatural to delegate certain tasks, but no task is too small and you should delegate things that you uniquely do not have to do in order to free up your time for higher leverage work. 
• Clarify the level of ownership your assistant has over your tasks.
• Try workflow recording.
  
  • It doesn’t take extra effort to hand things off to an EA. This is the best place to start if you have trouble delegating tasks.
  • This is really as simple as when you sit at your computer to do a task, turn on a Loom, and then that's it. Almost everybody in their own role says, "Nobody else could do this, it's way too complicated and easier to do it myself.”
  • Almost everybody overestimates the complexity of most tasks. It's really just pattern-matching. It turns out you record yourself doing that two or three times and then an EA can replicate that with 90% accuracy. You’ll be surprised at how quickly somebody can match whatever pattern it is that you're doing. And there's a lot less secret knowledge than people expect.
  • Try recording you working for a few hours then send it over to your EA and ask them if there’s anything in the workflow that they can take off your plate. Worst-case scenario, nothing comes of it and you didn’t have to spend any incremental time giving instructions. Best-case scenario, they’re able to take a few tasks off your workload in a way that you didn’t realize was possible.
  • Or, record one specific task and ask your EA “what do you think the process should be?” This is a way to de-risk the execution by having them repeat back what they watched into a step-by-step process or make recommendations for how to improve it.
• Try parallel tasking.
  
  • If you have a task to do, do it in parallel with your EA. Both of you do the same task, such that in the worst-case scenario, you just throw out their version and give them feedback on it.
  • What people usually discover is that people do a better job on a first draft with almost no context than you would anticipate. You just give them maybe by Loom some instructions and then you see what they put together.
  • If it doesn't work, you give them feedback. Worst-case scenario, you just don't use what they came up with. And then that's fine. You were in the same exact position now as you were before. But oftentimes what you'll discover is that it’s 80 percent as good as the one that you came up  with even though you thought it needed context that only you had.
  • It saves you a lot of time and you can build that confidence and you can give feedback. It might take two or three cycles of doing it in parallel before you can largely be hands off. This will get you more comfortable with delegating more responsibility.
• Look for ways to bring in semi-automation.
  
  • There are a lot of things that you can do where people are often afraid to give access to somebody like an EA to manage their social media account or email for example, because they think, what if they post something or what if they do X?
  • But you can always semi-automate, which is they take a screenshot or create a draft and then they propose what they think you should do and they'll say, I propose that you respond with this message, and over time you get better and better at teaching them what to ignore, who your contacts are, etc. They will get better at their proposed recommendations to the point where 95% of the messages are a quick yes even though you don’t trust them enough to delegate 100%.
• Use Async Video and Audio
  
  • This is going to feel unnatural for most people, but you should try to lean into recorded, asynchronous video and voice memos for delegation. It’s way more time-efficient for you and your EA, and it allows that video recording to be used as an asset in the future when new people need to be onboarded to the task. It’s way easier for someone to watch a recording than it is to have a new, synchronous onboarding call with every new person for every task.
  • When it comes to using asynchronous videos with EAs, the most important tip (and the one that takes some getting used to) is to always record in one take — it’s ok if there are awkward pauses or it's more of a stream of consciousness.
  • Async video is also a great way to do status updates and progress reports. It’s way more efficient than a live, weekly recurring meeting. Doing it in the form of content is more respectful of both your time and theirs.

Ask for Opinions/Input

• Executive Assistants possess a wealth of knowledge and have a unique perspective due to the level of visibility they have in the org.
• When the partnership has been established, consider having your EA participate in strategic meetings to provide valuable insights and contribute to decision-making.
• Actively seek their opinions and ideas on projects to benefit from their expertise.
• Acknowledge their contributions and let them know how their ideas have been incorporated.

Trust and Respect

Foster a collaborative relationship by treating your EA as a trusted partner and collaborator.

• Recognize that your EA brings valuable skills and knowledge to the table.
• Respect their professional judgment and allow them autonomy within their designated responsibilities when possible.
• Trusting their expertise leads to more efficient and effective outcomes.

Adjust and Adapt

Continually provide feedback and refine your working relationship as you both learn and grow together.

• Lean on the EA Manager as another outlet for sharing feedback or discussing ways to improve the partnership.

Working with an EA will enhance your productivity and enable you to focus on what matters most. By understanding their role, establishing open communication, and leveraging their expertise, you'll find a true partner in your EA.

Frequently Asked Questions

It's notoriously difficult to hire an executive who "fits" the org - what strategies can be used to ensure a fit prior to hiring?

For Wade at Zapier: “Probably the most important thing is to figure out what fit means. If you can't define it, you're going to a have a really tough time screening for that. For me, that's realizing that there are a few traits that are really important at Zapier:

1. Strong writing skills and async communication skills.
2. A willingness to be hands on (a lot of managers/execs delegate to the point of abdication). 
3. A history of getting stuff done / moving mountains. 
4. Once you have all those things well defined it gets a lot easier to assess for fit. The tough thing for me was I had to learn through trial and error what "fit" actually meant.”
   
   

Which executive position, such as CRO, COO, CMO, CPO, etc., is crucial to prioritize first when initiating the hiring process?  Any mental models?

From Wade at Zapier: “Depends on your existing team and where you have the most pain and the most to gain. For us, the founding team was pretty strong across product/tech/GTM so we needed less help there. We brought in the CFO to run all of G&A and that was a pretty good match. We probably should have been faster for VPE and Support because those functions had a lot of people and were scaling faster than our existing team/leaders could handle. Product and Marketing are the hardest. Product doubly so.”

For a generic SaaS company, a good reference: HERE

‍How do you evaluate execs and gain alignment as a fully distributed company?

Assuming the evaluation takes place after they've been hired, it's essential to observe the outcomes of their work closely.

From Wade at Zapier: “Just look at the output of the work. Is it meeting your expectations or failing your expectations? You can and should talk to them about what those expectations should be. They should have an opinion and you should respect it. If you don't respect it, that means they probably aren't a good fit for you. One great thing about remote teams is you can see all the exhaust of the work. “

Enforcing alignment is something CEOs actively drive. 

From Wade at Zapier: “I really have to force this. A lot of this comes from inspecting work. It's hard to pay attention to everything all at once. But I can pick something to go deep on and then watch for areas of misalignment and conflict. Then in the staff meeting I'll bring those up: "I heard one person say A and another say B. Those things can't both be true. What do we want to do?" The biggest areas of misalignment area often within the executive team. So I have to force them to debate amongst themselves. I had a great coach once say: "People don't need to get their way, but they do need to get their say." So let folks talk it out. Then make the call or choose someone to make the call. Walk out of the Zoom aligned and then call people out for not adhering to that. If someone breaks that alignment that's a big deal. I've moved on from execs that couldn't commit before. “

What framework have others used to predict which executive to hire 12 months ahead?

According to Vlad of Webflow: “I don't necessarily have a structured framework, but you often "just know" when some function is not executing at world-class levels. You hear it from other peers, board members, etc – around which areas need most leadership help, which search to prioritize first, etc. Basically trust your founder's intuition, often you know the answer, you're just avoiding the hard reality that a search is necessary.Best techniques to manage director-level leaders who will be layered in a few months with a vp hiring process kicking off? What are techniques to retain themAccording to Vlad of Webflow: "No silver bullet here, but I've found that framing their interim experience as a growth/learning opportunity is helpful. We also have a standard program for "extra duties" retention comp packages that include a sizable bonus (split into two chunks – half now, usually when their senior leader departs, and half 6 months later) and some added equity. That has generally worked, and generally we've seen that the interim experience legitimately accelerates their path to the next promotion (e.g. Director to Sr. Director). But so much depends on each individual and their motivations."

What is the difference between an executive and a director?

• Answer: Leaders set the plan (directors execute on it).
• Execs hire strong senior leaders underneath them.
• Execs have experience managing large teams.
• Execs donʼt learn on the job; they can either do it or they canʼt.