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:
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.
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.
Beyond engineering, the timeline for hiring leaders can differ. A breakdown for the primary roles:
What is the difference between an executive and a director?
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:
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:
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
Outcome: Reduce error rates by x%
Outcome: Speed up releases by y%
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:
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:
Understand the various models and patterns of success and failure within the role.
Inquire about their recommendations for your hiring process:
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
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:
Reach out to us if you need guidance on which specific search firms to consider and why.
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.
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:
Example: Reference Questions from Alumni Founders
Tactics for reference checks:
Questions to ask:
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.
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.
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.
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
Weekly Team Leads Meeting
Weekly Business Review
Box maintains an ongoing list of 12–15 strategic subjects. The meeting structure is below:
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:
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
Weekly Leadership Meeting (from when Apoorva was CEO)
Broader Senior Team Meeting
Weekly Meeting (Nat Friedman as CEO)
3-hour meeting on Monday. Agenda is the following:
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.
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.
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:
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."
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