Hiring and Managing Leaders

Defining the CEO’s Job

The responsibilities of a CEO evolve more than any other position as a business grows.

In the pivotal initial phases of a startup, the primary responsibilities of a CEO revolve around discovering product-market fit and establishing consistent customer acquisition. These challenges can take quite a bit of time to overcome. However, once you master these domains, the nature of a CEO's role undergoes a significant transformation. The job shifts from product creation and sales to the broader objective of building your company. 

To thrive in your new job, you must delegate most of your prior responsibilities.  Moving away from what you're familiar with - and often passionate about - is not easy. 

Over time, you must delegate most of the “executing”, e.g. coding, product design, customer support, and direct sales so that you can concentrate on guiding and expanding a burgeoning team.  Essentially, you transition to being the company's product manager—a role no one else can fulfill.  Rapid adaptation to this new role is crucial; otherwise, you risk becoming an obstacle to your startup's highest potential.

Building an exceptional company requires mastering the art of hiring top leaders and coordinating collective efforts behind the right objectives. 

Therefore, the responsibilities of a growth stage CEO encompass three elements:

1. Hiring top-tier leaders and ensuring they collaborate effectively towards a common goal
2. Outline your company's vision, strategic roadmap, and top metrics, and rally your team behind them.
3. Establish your operating cadence and foundational values.

You cannot hand off these three responsibilities to anyone else.  This is the work of the CEO and is never finished.  You will always be enhancing your leadership team, fine-tuning your tactical approach and performance indicators, and ensuring the pace and ethos of the company are optimal. 

CEOs usually remain engaged in 1-2 business areas, e.g. product or marketing, and also have non-operating tasks like fundraising, board meetings, and public relations.  Additionally, there's managerial paperwork like budget reviews.  However, the daily oversight of these areas should be handed over. This enables the CEO to prioritize most of their time on the above three tasks.  You can offer guidance to various departments, yet you must entrust your team with the actual execution.

We have structured the CEO Scaling program to help you thrive as a growth-stage CEO.  Recognizing that there isn't a singular path to being a great CEO, we intend to introduce you to a variety of strategies adopted by top CEOs and leaders. Our intention is to help you fast-track the evolution of your own framework on how to do this new, ever-evolving job in a way that stays true to you.

Building your Leadership Team

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.  While you may have some leadership hired, possibly homegrown from standout performers or mid-tier management hires, it's crucial to understand that you will also need leaders experienced in hiring, managing, and orchestrating the efforts of sizable teams.  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.

Ideally, you're planning leadership hires 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.

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

1. 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.

2. 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.
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3. 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.
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4. 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.
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5. 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.
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6. 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.

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.

How do you get started?

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. 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?

2. Engage with Leaders Prior to Recruitment

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, aim to forecast hiring needs at least a year in advance. 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.
• Tony Xu, DoorDash’s CEO, also maintains a list of current leaders. The reality is that not every leader will scale with the company and will either need to be replaced or layered. Tony categorizes 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, Tony starts 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.

3. How Search Firms Could Help

Approach your interactions with top-tier executive search firms with the highest regard.  

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 executive recruitment techniques, such as outreach strategies and screening methods. Top-tier executive 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.

Reach out to us if you need guidance on which specific search firms to consider and why.

4. 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 company operations. 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.

5. 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. Executive Compensation

• Donʼt be cheap. Leaders are expensive. Itʼs one of the more challenging aspects of hiring them. Expect that youʼll probably have to break some of your compensation rules to close them. But if you are hiring someone whoʼs going to transform your business, itʼs 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 an Executive or Senior Leader hire

• 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.

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Case Studies

Head of 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?

Head of 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."

Head of 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?

Head of 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.

Scale AI

Evaluation Criteria

Able to prioritize and evaluate investments: Track record of building a rigorous process around (a) evaluating all investments above a certain size from departments, (b) working with departments to forecast ROI, (c) evaluate performance against forecasted ROI

Has evaluated and understands existing practices: Has reviewed companyʼs approach on key metrics

Strategic thinking: Forward-thinking on how different business models, pricing structures, etc. impact reporting

Investor reporting: Proactive in identifying value-maximizing ways to report performance to investors and auditors

Cultural fit: 1) Aligned with company investment philosophies and 2) Compelling examples that demonstrate at least 5 of 8 values

Strong external presence/capabilities: (1) Track record of interacting directly with investors, board members and (2) Track record of managing private financing rounds end-to-end (i.e., requiring minimal day-to-day oversight from CEO/founders)

Experience managing a team with a broad mandate that includes:

• Strategic planning, analysis, forecasting
• Treasury, cash management, accounting
• M&A
• Board meeting preparation

Audit preparation and experience: Has led a team that underwent a third-party audit

Team management experience: Ability to hire and retain high-performing team and 

experience in managing a team of 10+. Set challenging and productive goals for team, keep team accountable for actions, provide leadership and motivation, provide resources and support, use checkpoints and data to track progress, set up systems to measure

Case Study

Revenue recognition‍
Consider ratable recognition vs. usage (or consumption) based recognition. Assume that a contract can be interpreted in either way. From a business perspective: How do you determine which model to adopt? How do you determine if/when to transition from one to the other? Note: This topic isn't about technical accounting merits of methods, but more about how you think the business should approach this choice strategically.

Cost allocation‍
Companies with large or complex operational aspects (e.g., Palantir, Uber) seem to approach cost allocations in different ways. How should our business think about and approach the allocation of these operational costs between cost of sales and operating expenses?

Top-level metrics‍
ARR (annual recurring revenue) is a standard SaaS topline metric. Some infrastructure companies (e.g., DataDog) have adopted a variant of ARR (e.g., annualized revenue run rate) as a headline metric. Other infrastructure companies (e.g., Twilio) use total annual revenue (though this seems to get called ARR by investors). How should our business think about using this top-line metric—or others like it—over time?

Headcount/OpEx planning
‍Assume that a business has top-line unpredictability, and that massive customer growth deals can also come with near-term price and margin pressure, leading to cash burn unpredictability. How should our business manage OpEx investment given this volatility?

Leadership Hires

‍Scale’s Executive Hiring Criteria

General Talent Bar: Scale strives to recruit notable executives, striving to hire only when there is a robust “yes”. The ideal scenario is where people would be eager to work for that executive in an alternative scenario. In a broader sense, Scale is in pursuit of:

• Culture [via interviews and backchannels]
• Team Chemistry [via interviews]
• Proficiency [via interviews and backchannels]
  
  

I. Must have skills:

Talent Beacon: Adept at attracting and hiring high-quality talent, maintaining stringent standards for skills. Must be personable and proficient in advocating the vision. Ideally possesses a substantial network of relevant individuals.

• Validation Method: Analyze their historical hiring records, preferences, and network.

Mental Agility: Provides quick and clear thinking. 

• Validation Method: Evaluate their aptitude for grasping new concepts and challenging conventional thoughts in discussions.

Leadership: Demonstrates the ability to motivate teams, convey complex ideas succinctly, and navigate through turbulence or difficulties. 

• Validation Method: Inquire via backchannels, analyze their leadership principles, and evaluate their past crisis management through backchannels and team attrition rates.

Chaos Navigator: Can steer through disorder and imperfection, continually progressing towards the ultimate objective. 

• Validation Method: Review past professional experiences and inquire about management strategies during tumultuous periods through backchannels.

Functional Mastery: Hire individuals who bring expertise and passion for their domain. 

• Validation Method: Backchannels and internal evaluations, with potential third-party interviews.

Frugal, Lean, and Resourceful: Achieving more with fewer resources (financial, personnel, and time). 

• Validation Method: Evaluate their resource expectations and the logicality of their resource requisitions, and assess the impact-to-organization efficiency ratio.

Hard working: [Self explanatory]

• Validation Method: Evaluate their willingness for intensive work contexts (ideally 50+ hours per week?) and ensure their previous engagements required diligent work ethics.

Strategic and Holistic Thinker: Simultaneously manages overarching and minute details. 

• Validation Method: Assess their ability to elevate observations to strategic levels and spot systematic issues.

Ambitious: Desires to realize monumental achievements. 

• Validation Method: Analyze their career progression and understand their future aspirations.

Detail-Oriented: Keen to delve into particulars, identify discrepancies or issues, and occasionally handle tasks directly. 

• Validation Method: Backchannels and inquiry methods that drill from high-level to detailed responses.

Profound Problem Solver: [Evaluate from past roles + questions]

• Validation Method: Present a difficult issue and observe their engagement and innovativeness in proposing solutions.

Ownership: Treats every issue as their own and assumes accountability. 

• Validation Method: Assess if they identify and address problems without prompting and if they devise solutions for issues beyond their control.

Adaptable and Humble: Modifies past strategies to our requirements and adjusts strategies in real time. 

• Validation Method: Evaluate their adaptations of past strategies to Scale’s necessities.

Collaborative Contester: Jointly tackles problems while challenging assumptions for superior outcomes. 

• Validation Method: Backchannels and evaluation of their respectful challenges during conversations.

Proactive Innovator: Instigates improvements and resolutions unsolicited. 

• Validation Method: Through backchannels, assess their past pace and proactive actions.

Resilience: Maintains belief through highs and lows. 

• Validation Method: Assess their past loyalty and stability through backchannels.

First-Principle Thinker: Robust logical thinking and reducing beliefs to foundational assumptions. 

• Validation Method: Through a series of “why?” questions, assess their response depth and if they examine your propositions to fundamental assumptions.

Metrics-Oriented: Employs metrics for gauging and directing successful results. 

• Validation Method: Understand their success evaluation methods, team management, and planning processes.
  
  

II. Nice to haves:

Knowledge about AI

• Validation Method: Discuss past projects, challenges, and delve a layer deeper into their understanding.

Context in operational businesses 

• Validation Method: Review of resume.

Technical/Engineering Background 

• Validation Method: Engage in technical discussions and review resume.

Customer-Focused 

• Validation Method: Explore their historical decision-making and gauge the extent of their commitment to customer service.

Ability to move fast

• Validation Method: Discuss their views on team pace, planning speed, and approach toward grand objectives, along with considering backchannels and past company cultures.

Experience at a hyper growth company

• Validation Method: Resume.

Stellar people manager

• Validation Method: Evaluate through backchannels, observe team attrition rates, analyze reputation, and explore their employee development frameworks.

Tony Xu's Criteria for A+ Executives

Characteristics

• Bias for action. Most candidates are good at “textbook math” and communicating ideas, but few are resourceful and have a bias for action. One way to test for this characteristic is to look at the amount accomplished per unit of time at each role. The best potential executives accomplish a lot in what can seem like short periods of time. Another way to test this is by giving them an assignment. Assignments range from asking candidates to analyze unstructured sets of customer data, to asking them to acquire customers within a 24 to 72 hour period, to asking them to come up with a 6 to 12 month plan depending on the role. Assignments are both useful indicators on the quality of output and how they work. They also ensure that the person is willing to do the work, which is the biggest risk for more senior hires that are used to delegating to team members.

"Usually in exec land what that means is that they've made mistakes I've learned because most execs they tend to play pretty safe because it promotes job security and longevity in the roll. execs though, who tried and failed I found and ideally are also later successful. Like they tend to be the best better hires, because they're actually willing to do something versus like, just follow whatever the standard playbook is or best practice in quotes."

‍

• Detail oriented (especially important in early days) and high slope.  If your company has about 30 to 50 employees, this attribute matters a lot as you need your leaders to be 80% player and 20% coach. At the early stages of growth you need a leader who is a builder, can take risks, obsess over the details, and course correct as needed. When you ask them about their prior roles, they are able to walk through process and decisions down to the nth level of detail. If this is true, they’ll will apply that same level of detail to their new role. You also want candidates with high slope. Particularly in the early days, candidates may not seem super experienced, but have accomplished a lot in seemingly little time. Testing for detail and high slope are critical.

"Like one tell I have on slope, it's just kind of the mathematical equation of slope, which is like, alright, well, how much work did you do per unit time? And it doesn't have to be like, Oh, you worked at some awesome big company, like, you know, Facebook or Google or that that's cool to like, well, we'll look at that too. So like to this day, like to give you a version of how that translates. Generally, like people will look really impressive on a sheet of paper and they'll have, I don't know 10 years on Amazon, like 18 years at Meta or something but usually how that works is it's like a sum of like a lot of one to two year or three year experiences. And so I decompose that and look at like, alright, well, how much did you achieve? Like and what is your rate of achievement? It's probably a decay function. It's like some concave function. But really good people you want to actually really impress you. There is this one awesome person that I was never able to recruit. He made VP at Amazon in 8 years, which is unheard of for a college grad. Usually, it takes like 15 years or something and he just did it in half the time. If you looked at how he did that, it was four stints (different projects) with super impressive achievements in each rotation. And you know that the super young age of 34 is on their equivalent of their senior management team."

‍

• High content to word ratio. A good way to test this is ask yourself how much do I learn if I spend 30 minutes with a person? A great executive is pretty efficient with their insights and this is a signal they will be able to communicate ideas with you, the board, and the team.‍
• Ability to hold opposing ideas at the same time. Executives will likely come in with a playbook that worked at their old company. At the same time, the playbook that worked at their old company might not be right for their new company. The best executives understand this fact and think about problems from first principles before suggesting a solution.

"The ability to hold two opposing ideas at the same time...A lot of times this is to test for the like willingness to give up some of their priors. They're gonna come from some awesome company, right? And that's why you recruited them, but they're gonna think that's how they should just do things for your company. And that might be true. Their likely may be some like, transpose function that works. But candidly, I think all of our best people, they they realize things from first principles that which things worked and which ones didn't work."

‍

• Exceptional at hiring second level leaders. The best executives will be able to recruit exceptional people to join them. One way to test this is to ask the potential executive about the best teams they’ve built and where all the people are now. If they’ve truly built great teams, their reports would have scaled, leading teams at other impressive companies
• High degree of followership. The best executives are able to bring other people with them. One way to test for this is to ask candidates for three people that would join the company after the candidate joined. Call these people and ask whether they’d follow your candidate.

"We look for people who have strong followership. So I'll ask them literally to give me a list of like three to five names of people that would join our company after you join. And I will call them individually and ask that question just to call BS [and see] if that is true or false. It's what we call followership."

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• ‍Continuous improvement. The best executives constantly try to improve their performance or their functions. In short, they aim to get 1% better each day. One way to test for this is to ask candidates about one thing they are trying to improve on. Typically, the best candidates are working on something even if it's not work related.

"The last one is what we call getting 1% better every day, which is I tend to ask someone, what's something that you're working on that you're just trying to improve upon? It doesn't have to be like a professional thing. It'd be a personal thing like, I don't know cooking or tennis or whatever. And I found that the best people, they tend to always be trying to improve in some way like their position on something. And that is a nice composition of curiosity and persistence, and humility."

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Reasons for Mis-Hire

• Insufficient time investment and giving in to desperation. Spending adequate time with candidates is crucial. If you get the hire wrong, they will build a team and will take months to unwind. If you get the hire right, the person can pay off orders of magnitude more than the time you put into the investment and recruiting process. Do not give in to the pressure to make the hire before you feel 100% comfortable.

"Causes for when I've screwed up - I gave into my desperation. That's that's probably the single biggest thing I would say. Actually, for both hires [early CFO and Head of HR] that was definitely true. Just contextually I probably spend myself 15 hours or so maybe 20 with the candidate and collectively the candidate will spend about 30 to 40 hours with our company before we will make an offer. Now there are ways out right it's not like every candidate you spend 40 hours with but with like people that you're getting pretty close with. My thesis on this is like look, this is a very high return to input decision where if we do a good job, this person can pay off like 10s of 1000s of hours, and what's 40 hours right? It's gonna be a good return. And you'll also get better signal when you spend more time. I don't think that I'm a good enough assessor of anyone, like in an hour that I can tell whether you're for real or you're not I'm getting better but I don't think I'm perfect."

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• Giving in to pressure to make a hire you don't actually need. Hiring an executive you don't need is another common failure case. It usually comes from someone you trust recommending a hire or you feeling the need to address a function without truly understanding what you are looking for. Tony's advice is to assess if you have product-market fit in that function. If you do, it's likely a good time to hire as you'll need someone to hire and manage people. If you don't, his gut instinct is you are probably better off waiting .

"It [referring to a mis-hire] was just one of these things where I felt like I don't know like I got pressured into without me feeling like you know, I knew what I was looking for. And so my biggest advice at your stages, like, you know, what are you looking for?"

"I think it's a little bit case by case but I think it has something to do with this notion of like, do you already have the product market fit within that function? And if you do, then yeah, I think you're going to need recruiting and all that good stuff. More rigor, probably in that function. If you don't, then my gut is you're probably better off not making the hire. The reward risk ratio is not there."

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Other Common Criteria for Executives

Criteria to Evaluate Executives (Generic)

• Objective and structured thinkers
• Brainstormers (willing to start from a blank slate and work together)
• Strategic and framework-oriented

Other

• Itʼs generally better to hire too senior instead of too junior. Management requires experience. That said, you need to test they will actually do the job. If they are talking about how big of a team they need from day 1, this is a warning sign.

What does Joshua Reeves (CEO of Gusto) look for when hiring leaders?

In this case study, we highlight the following four processes at Gusto, designed to ensure that leaders brought in not only meet the role's qualifications, but also align with the company’s culture and values:

1. Executive interview process
2. Calibration and Support After Hiring
3. Managing Senior Executive Performance
4. Frameworks for Goal Tracking and Feedback

Remember that the timing for implementing hiring playbooks, best practices, and frameworks below can vary based on the size and complexity of your organization. While larger companies may need these processes sooner, smaller startups can gradually introduce them as the need arises. The key is to maintain alignment, clarity, and open communication throughout the hiring and management processes.

I. Executive interview process:

1. Initial Screening:

• All executive candidates go through an initial screening, typically conducted by a member of their People team.
• This initial conversation helps Gusto gauge the candidate's interest in the company and assess their fit in the role

2. SPOT Document:

• Gusto uses a document called SPOT (Specifics, Purpose, Objectives, and Talk) to get clear on the criteria for the executive role.
• It outlines the specific qualifications they’re seeking, the purpose of the role, and the objectives the candidate will be expected to achieve.
• The SPOT document helps ensure alignment and clarity in their hiring process.

3. Match Talks:

• Before bringing candidates onsite, Gusto often conducts match talks, which involve in-depth conversations with candidates.
• These talks serve a dual purpose: inspiring the candidate about Gusto's mission and values and helping them assess whether they're a good fit.

4. Onsite Interviews:

• Candidates who pass the initial stages are invited for onsite interviews.
• Each interviewer has a specific role and set questions, ensuring a consistent and unbiased evaluation.
• Gusto typically has no more than 9 interviews, each with a unique focus.

5. Homework Assignment:

• Candidates are given a homework assignment with a specific prompt.
• They are expected to spend a minimum of five hours but no more than ten hours on this assignment.

6. Panel Discussion:

• Candidates participate in a panel discussion with four or five team members.
• This session allows them to hear feedback and insights from their team and engage with the audience effectively.

7. Values Interview:

• In a 20-minute values interview, Gusto assesses the candidate's alignment with their core values.
• Gusto looks for individuals who demonstrate a "driver" mindset and are in it for the collective success of the team.

8. Clear Communication of Expectations:

• During the interview process, it's crucial to be specific about what Gusto expects the executive to accomplish over the next 12 to 18 months.
• Clear communication of expectations helps ensure alignment and clarity from the beginning.

II. Calibration and Support After Hiring:

After an executive is hired, it's essential to set them up for success and maintain alignment with their role and the company's objectives. Here's how Gusto achieves this:

1. Onboarding and Explanation:

• In the first few months, provide the executive with a comprehensive understanding of the business.
• Explain the company's vision, mission, strategy, and design, and encourage them to share their observations and feedback.

2. Regular Check-Ins:

• Schedule regular check-in meetings, ideally two hours at the beginning and end of each week, for the first three months.
• Use these meetings to calibrate, discuss progress, and address any concerns or questions.

3. Open Communication:

• Create a safe space for open and candid communication.
• Encourage the executive to share their observations and concerns, and be open to feedback.

4. Clarity of Expectations:

• Make sure the executive understands your expectations and the company's strategy.
• Clarify your thought process and share key insights, such as how you pitched fundraisers or recruited talent.

5. Respect for Sacred Company Values:

• Identify aspects of the company culture and values that are essential to you.
• Communicate why these values are important and be open to discussions on how to align with them.

III. Managing Senior Executive Performance:

1. Focus on Systems, Not Blame:

• When goals are not met, focus on understanding why it happened rather than assigning blame.
• Encourage discussions about the reasons for missing targets and what can be learned for future success.

2. Private Feedback:

• Provide constructive feedback in private, emphasizing a commitment to improvement.
• Avoid public criticism, as it can undermine team morale.

3. Clarity in Communication:

• Ensure clear and specific communication of expectations and results.
• Use one-on-one meetings to assess progress against agreed-upon initiatives.

4. Effective Apology:

• As a CEO, be willing to apologize when necessary, both for not meeting commitments and for any mistakes.
• Master the art of an effective apology to build trust with your team.

IV. Frameworks for Goal Tracking and Feedback:

1. 1:1 Document:

• Utilize a structured 1:1 document to track progress and outcomes.
• Start each meeting by reviewing results and key initiatives, fostering alignment.

2. Radical Candor:

• Embrace the Radical Candor framework, which involves challenging directly and caring deeply in communication.
• Balance deep care with crisp challenges in your feedback.

3. Clarity in Communication:

• Ensure that your communication with executives is clear, specific, and results-focused.
• Articulate what you need from them and be fearless in addressing issues.

Generic Executive Interview

Detail Orientation / Testing for "Builder"

• Can you briefly explain your company's product and go-to-market? They should have command of the product and process end-to-end. They should be able to cover value proposition, sales motion, customer/buyer, how expansion is driven, implementation/customer success, and competition.
• What are you personally responsible for? What about your team? What about other executives at the company?
• How do you segment your customer base? How does the GTM motion differ across each?

Hiring and Team Building

• What are the roles and responsibilities on your team?
• Can you take me through each of your direct reports and their strengths/weaknesses?
• Who are the best external and internal hires youʼve made?
• Can you tell me about a bad hire?
• Who are the top 3 people youʼll try to hire if you end up in this role? Will they follow you?
• What are your managerʼs strengths and weaknesses? If I call them, what will they say are yours?
• Tell me about an executive youʼve had a challenging relationship with.

Decision Making

• What KPIs or metrics do you regularly look at? Tell me about a meaningful decision you made based on one of them.
• Give me an example of when data/metrics have led you astray
• Do you spend time with customers? How much? Describe a decision that you've made from customer feedback.

Communication

• What are your companyʼs top strategic priorities? What is controversial about the strategy?
• What would you do differently if you were CEO?
• What are the lowest and highest performing parts of the business? What about your org? How do you know?

EQ & Habit of Self-Improvement

• What businesses have you learned the most from observing? What companies do you most admire?
• If you could go back in time a few years, what would you do differently?
• What is the #1 area you've improved in your current role?
• When in your career have you felt most accomplished?
• What is the toughest feedback youʼve ever received?
• What do you think will be the biggest challenge coming to our company?
• What would you do over in your career if you had the chance?

A note on detail orientation. At the early stages of company building, hiring failures often stem from a leader not willing to "do the work" in the role. By testing for detail orientation you get to the bottom of whether the leader actually went into the weeds of decision making and process at their company or if they delegated and made decisions from exec land.

Considering a 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 executive 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 executives serve a year or two as a chief of staff to leaders like Jeff Bezos or Andy Jassy, after which they transition to other leadership capacities within the organization.

How to get the most out of your EA?

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 depend 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.

On Managing Leaders

1. Ensure Proper Onboarding

Consider the onboarding process as you integrate the leader into a team, rather than merely introducing them to a role. In the initial 60 days, their foremost task should be to absorb as much as they can about the organization. This involves interacting with pivotal team members, not just their direct reports, and scheduling extensive weekly meetings with you for guidance and clarity. Equip them with foundational knowledge about the industry and your enterprise, encompassing aspects like company history, culture, customer base, competitive environment, and primary challenges.

For instance, at Gusto, leaders are expressly informed that their initial months should be dedicated to familiarizing themselves with the company's operations and dynamics. It's only after this immersion that they're entrusted with implementing changes. When the COO of Intercom came on board, she wasn't immediately assigned direct reports. Instead, she dedicated her initial months to conducting numerous one-on-one sessions across the organization. In another instance, a founder prepared an executive for their role by providing extensive preparatory reading material, compiling a list of 30 key individuals for meetings, arranging personal dinners with fellow leaders, and timing a management retreat to align with their joining.

After the first 60 days, the executive should have come up with an initial plan. Engage them to share valuable insights and feedback, and ensure that this plan is revisited and assessed at consistent intervals.

2. Establish Objectives and Ensure Accountability among Leaders

For new CEOs, the concept of delegation is understood, but its execution can be challenging. Until now, every decision might have passed through you and your co-founders. Extracting yourself, especially from segments you're passionate about, is tough, but necessary for growth. Once you've positioned a competent leader and set mutual goals, trust them to take charge and make autonomous decisions.

Assessing a leader’s performance is straightforward: they should achieve their targets and maintain a content team. If these criteria are met, your delegation is successful. Focus on outcomes rather than dissecting their methods. Efficient leaders will preemptively identify and address issues, keeping you informed.

To gauge the satisfaction of a leadership team, solicit feedback from their subordinates. While earlier you could gauge morale intuitively, your current position requires a more systematic approach. Gather insights from team members (skip levels), amalgamating their feedback with your own perceptions. One leader shared that actionable feedback emerged from structured tools and consistent communication.

Skip-level roundtables, where you engage with team members directly, are effective for understanding team dynamics. Regularly convene groups to discuss company positives and areas of improvement. Structure these sessions with specific inquiries and identify recurring themes. Share the findings (while maintaining confidentiality) with the concerned executive. Such interactions also bolster a culture of approachability.

Offer clear, precise feedback to leaders. Balance constructive criticism with positive reinforcement. Regular feedback, especially during the initial phases of collaboration, is essential. Additionally, provide comprehensive written feedback biannually. This written record should reiterate previously discussed points.

3. Establish a Cohesive Team, Rather Than a Group of Independent Leaders 

Your objective is to cultivate an aligned team rather than isolated leaders with independent goals. This cohesion emerges from team interactions and personal connections. Regular leadership meetings and retreats facilitate this. Leadership meetings should be both enjoyable and productive. An atmosphere devoid of enjoyment indicates underlying issues. Effective meetings promote open dialogue, problem-sharing, and collaborative problem-solving. While you steer the direction, leaders should actively participate.

Periodic management retreats also promote team unity and combat against political work atmospheres.

Example: Executive Meeting Structures

Weekly Executive Team Meeting

• Running agenda each week to discuss big company level topics
• Goal is to make sure the executive team stays connected and to discuss big strategic topics
• The output of these meetings is typically decisions on big strategic and hiring topics

Weekly Team Leads Meeting

• Once they scaled past ~80 people this became important. Its a meeting for directors and above
• Max uses this time to broadcast what is top of mind for him and the leadership team at Faire
• The goal is to ensure alignment on key goals. It is impossible to be too repetitive

Weekly Business Review

• Weekly meetings reviewing all key metrics in the business
• If metrics are off, they understand why and how to address missed performance

Box maintains an ongoing list of 12–15 strategic subjects. The meeting structure is below:

1. Examine their 12 primary indicators.
2. Analyze the sales pipeline.
3. A rapid-fire session where each participant highlights their most pressing issues.
4. Break for lunch.
5. Focus on 1-2 strategic areas, typically summarized in three slides each.

Weekly Leadership Meeting

One-hour meeting on Tuesday at 1pm. Meeting is structured around a Google Doc where key company metrics are automatically populated each week as a status update. Within the doc, each executive also has a section to answer the following questions:

1. Red/yellow/green on professional and personal things
2. Key focus areas for the week
3. Things youʼre concerned about
4. Things you need help on

People read and comment on the doc for the first 10 minutes. This allows little things to get resolved via the comments. The remaining 50 minutes they discuss key topics that Wade has curated.

Monthly Business Review

• Monthly OKR meeting to track performance versus goals

Weekly Leadership Meeting (from when Apoorva was CEO)

• Apoorva sets the agenda over the weekend. 3-hour meeting on Tuesday
• Team reviews key metrics from prior week on Monday in advance of Tuesday meeting
• Discussion revolves around founder agenda + discussion of outcomes from last week

Broader Senior Team Meeting

• 1 hour meeting on Wednesday. Includes a broader set of senior team members
• Use the time to communicate what was discussed in the weekly executive meeting

Weekly Meeting (Nat Friedman as CEO)

3-hour meeting on Monday. Agenda is the following:

• Discussion of Sunday Snippets. Every Sunday, leaders share "Sunday Snippets" on Slack. These are a summary of what they are working and what's on their mind
• Nat shares what is on his mind
• Discussion of predetermined agenda
• In the final hour, they invite others to present. This makes people feel like they are being heard and it is a way to reinforce cultural values you think are important at the company

Examines the KPIs from the past 12 weeks, assessing how each week's figures have evolved year-over-year and how they align with set targets. Everyone is encouraged to raise questions regarding any KPI.

The result of the meeting is a list of actionable steps, either to modify a business aspect or to alter the KPI set if it isn't yielding the necessary data for decision-making.

Rather than using slide presentations, Twitch employs Amazon-inspired written documents that adhere to specific guidelines. For instance, growth rates should always be accompanied by their base values, and any number presented should be contextualized with its year-over-year change and its relation to the goal.

The founder maintains a continuously prioritized list of subjects, organized based on their significance. Prior to the meeting, he shares a concise written overview or vision related to one of these subjects.

While they seldom cover all the topics, the prioritization ensures concentration on the most crucial matters. The founder contemplates two key questions: (1) Is any item on the list crucial enough to halt ongoing tasks? (2) If a topic isn't addressed within the upcoming week, is it even necessary to discuss it?

Example: Executive Offsite Structures

At the start of each quarter, they conduct two-day retreats. For the initial one and a half days, only the CEO and their direct reports participate. The wider management team is incorporated for the latter half of the second day.

They hold an offsite during the first week of the quarter's final month.

The objectives are twofold: (1) to ensure they are on course for the current quarter and (2) to establish targets for the upcoming quarter. They refrain from non-work-related activities, given the existing positive dynamics and enjoyment in their daily operations.

Annual offsite. Founder doesn’t feel they need to do it more as the team collaborates well.

Annual planning offsite, complemented by afternoon sessions during organization-wide gatherings.

4. Act Decisively When a Leader Doesn't Fit 

When an executive isn't aligning with the company's needs, it's crucial to take prompt action. 

Leaders are brought on board for their expertise. While feedback is essential, they shouldn't be continually given opportunities to rectify the same issues, nor should they be placed on extended performance evaluations. Such leniency can diminish team morale. Ideally, decisions regarding their fit should be made within 60-90 days.

Managing a business often feels like juggling numerous tasks simultaneously. A proficient executive should alleviate some of this burden, handling certain aspects, ensuring smooth operations, and resolving issues. On the contrary, an ineffective executive might seem to add to the challenges.

A straightforward indicator of an executive's compatibility is your comfort level with them. If you find yourself avoiding interactions or dreading scheduled meetings, it's a clear red flag. 

One founder mentioned, "Engaging one-on-one with an executive should be a valuable, anticipated interaction. If it's something I dread, it's an indication of a potential vacancy." Another emphasized, "I've observed a direct correlation between my rapport with leaders and their success. Not connecting personally often spells failure."

It's not unusual for executive placements to falter. Startups often see a 50% failure rate during their initial wave of executive recruitment. Even a seemingly fitting executive might only stay relevant for a period, possibly two years. Rapidly scaling companies might outpace an executive's capability or interest.

When communicating an executive's departure, ensure the message is conveyed respectfully. Publicly acknowledge their contributions. Such decisions leave a lasting impression on the remaining team, and it's crucial they perceive the leadership as decisive yet compassionate.

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."