Hiring and Managing Executives

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.  

Succeeding in your New Role

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 a Great Company

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 executive leadership team.  The task of recruiting and managing top-tier executives 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 seasoned executives.  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 an executive 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 exec 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 executives 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 executives 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.
   ‍
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.
   ‍
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.
   ‍
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.
   ‍
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 executive 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 executives 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.

Frequently Asked Questions: 

What is the difference between an executive and a director?

• Answer: Executives 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.

Hiring executives

Recruiting executives 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 executive 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 an executive

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 Executives Prior to Recruitment

Before bringing on an executive 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 Executive 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 Executive 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 executives take 6-12 months to hire. 
• Actively expand your pool of potential candidates. Whenever you interact with executives, 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 executives 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. Executives 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 executives 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 how 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.

6. Case Studies

DoorDash: Tony Xu's Criteria for Executive Hiring

Tony shares his criteria for hiring great executives based on his experience at DoorDash. He also shares mistakes to avoid.

Benchling: VP of Engineering

A deep dive into Benchling's interview process to hire their first VP of Engineering

Faire: VP of Engineering

A deep dive into Faire's interview focus areas when hiring their first VP of Engineering

Scale: Executive Hiring Criteria

A deep dive into Scale's criteria for evaluating executives successfully

Gusto: Executive Hiring Criteria & Process

A deep dive into Gusto's criteria for hiring, interviewing, and managing executives

Ironclad: VP of Sales

A short summary of Ironclad's VP of Sales hiring process

On Managing Executives

1. Ensure Proper Onboarding

Consider the onboarding process as integrating the executive 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, executives 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 executives, 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 Executives 

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 an executive'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 executives will preemptively identify and address issues, keeping you informed.

To gauge the satisfaction of an executive's 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, amalgamating their feedback with your own perceptions. One executive 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 executives. 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 Executives 

Your objective is to cultivate an aligned team rather than isolated executives with independent goals. This cohesion emerges from team interactions and personal connections. Regular executive meetings and retreats facilitate this. Executive 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, executives 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, executives 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

Examine 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 an Executive Doesn't Fit 

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

Executives 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 executives 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.

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.

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 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 them?

According 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 sizeable 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."

Additional Resources

Generic Executive Interview Questions

A list of generic executive interview questions. We will continue to add to this over time.