5

Building your leadership team

Evolve your time as CEO from doing to managing

As you scale beyond tens of people into the hundreds, your role as founder needs to undergo a dramatic transformation. You’ll no longer be involved in every hire, or even know everyone’s name. You’ll inevitably feel a weight of responsibility for the livelihoods of so many others. You’ll have multiple investors, and will probably have less than majority ownership or control of the company. You’ll feel yourself pulled away from frontline activities and the raison d’être behind your business, and sucked more deeply into running the company.

These changes are both inevitable and in the best interests of the company. But adapting to them can be challenging, and you need to adjust the way you spend your time accordingly. One of the most crucial things you need to consider is how to create CEO leverage—bringing people on board and creating processes that can channel and amplify your actions, freeing you up to focus on what only you can do.

You need to become the conductor rather than the musician.

Martin Mignot, Index Ventures

Several of the founders we interviewed for this book had things to say about this transition in their role:

In my first startup, I still found myself coding on the side when we were 80 or 100 people, which maybe wasn’t the best use of my time. As a developer, it was tough for me to rewire my brain so that I didn’t see a day without coding as a wasted day. But leading is about getting leverage through others.

Jason Citron, CEO & Co-Founder, Discord

In the early days, I just had to put in the sheer hours needed. I can now create windows when I can be more deliberate, and my focus is on celebrating our success, while ensuring we retain humility and grit. But I still can’t take my foot off the gas—there’s just a different shape now to how I achieve.

Kate Ryder, CEO & Founder, Maven

You need to fight against the inertia of, ‘I’ll keep doing what I’m doing now.’ You need to regularly realign your time against the real priorities.

Matt Schulman, CEO & Founder, Pave

I am now surrounded by a lot of doers, but ideas often originate with me. With hundreds of people in the company, I focus my internal time on upleveling my executive team, while maximizing the external time I have with customers plus media.

Anonymous Founder

You might hope that you’ll spend less time on people, but you won’t. It will just morph into other types of people stuff.

Divinia Knowles, The COO Coach

Now that we’re at a larger scale, my role has developed into founder plus executive. As a founder, I can bring passion, product instinct, domain expertise and intimate knowledge of the company; As an executive, you need to really focus on leadership and operational excellence. Being able to combine both is a real privilege.

Abakar Saidov, CEO & Co-Founder, Beamery

A key part of my role now is to bring clarity and simplicity. I’m the only person in the org who can say, ‘We’re not going to do X, and that’s ok.’ Otherwise everyone wants to perform and achieve, and that can overcomplicate and reduce effectiveness.

Rodolphe Ardant, CEO & Co-Founder, Spendesk

But there’s a balance to be struck here. While you need to step away from the frontline, you also need to consider where you, and only you, can make the most impact, and feel the most fulfilled. If you have a “superpower” it brings you joy to use, then carve out time and formal responsibility for exercising it. For many founders, this revolves around product, and they love to remain hands-on with product review sessions. The key thing is that you do this in a way that always provides learning and development progress to other members of the Product team. The same principle applies if your superpower is in sales, operations, or anything else.

Inspiration and vision are very important. But my value also lies in translating these ideas into products. If you disconnect completely from building, it’s too easy for folks to misunderstand what they should be building, and you can end up with hallucinations! So I see my role as more like an editor, working with raw material. At any time, certain areas of the business need more editorial input than others. For areas that are ticking, I’m offering inspiration. But for areas that are misfiring or new, I lean in.

Jason Citron, CEO & Co-Founder, Discord

Hanno [Personio’s CEO] is good at choosing what he wants to do, and at pulling back when he’s too deeply involved in something that he shouldn’t be. It’s impressive ‚and also very rare.

Maria Angelidou-Smith, CPTO, Personio

Core executives

At the start, hire just a few executives

In the early days, it rarely makes sense to hire executive-level talent across more than a couple of functional areas. You won’t be able to afford it, and you’ll also struggle to access and land high-caliber candidates. You’re also unlikely to know the precise profile and experience that would be most helpful for your company. In general, we advise you not to hire more than three executives by the time you reach 50 people.

MOST COMMON EXECUTIVE HIRES BY 50 HEADCOUNT—PERCENTAGE OF COMPANIES MOST COMMON EXECUTIVE HIRES BY 50 HEADCOUNT—PERCENTAGE OF COMPANIES

Nonetheless, it can be beneficial to have seasoned professionals to guide your early thinking. The concept of “fractional execs” has therefore gained ground in recent years—that is, former operators who spread their time across a number of startups during the period before a full-time executive is hired into the role. There is a growing talent pool on the fractional side, particularly for People, Marketing and Finance execs.

The best founders know what they don’t know. Working with fractional executives can help them to accelerate their learning curve, so they know more clearly who they’ll need in a full-time capacity later on. The risks and costs are lower than diving straight into a full-time hire. For example, which marketing channels and competencies should you double-down on? Doing this before you hire permanently can bring clarity and focus to your role.

Sandra Schwarzer, Index Ventures

There are still risks with fractional executives. Are they an outsider or an insider? Are they doing actual work or only advising? It’s important to have clear and aligned expectations around these questions. It may be that a more traditional advisor role is better suited. But if there’s heavy lifting to be done, you want an “insider” mentality.

We favor constructing these relationships as part-time employees rather than as contractors, with a minimum of three days per week. While this can be less favorable from a tax perspective, the “psychological contract” is stronger. Another option is a “burst exec”, who is contracted (three to five days per week) for a few months to deliver a defined project or objective. For example, a People Leader who helps to deliver the initial vision, mission and values documentation plus internal rollout. Or a Finance Leader who helps you run your next fundraise. The worst type of arrangement in our experience is a one day per week freelancer paid per diem, who never really gets under the skin of who you are or what you need to focus on.

You might find it helpful to engage one or two fractional functionally-oriented executives during the first period of scaling, but construct these relationships as either “burst contracts” or as part-time employees.

Craft your inner circle as you grow

Even with co-founders to share the load, you will need to increase the number of experienced and specialist functional leaders as you scale—people you can comfortably delegate to, and who know what “great” looks like without having to learn it through trial and error.

These executives will be people who can operate at either a VP or CXO level, who can assume responsibility with a high degree of autonomy to run an entire functional area of the business. They will always (with a 95% likelihood) be better qualified than you or any other co-founder to run their function at scale.

It all comes down to the quality of your executive team. Building this team is your number one priority. It just makes everything else easier.

Daniel Ek, CEO & Founder, Spotify

Building a leadership team also brings its own challenges, such as managing internal comms now that there’s a new layer between you and the broader team. Most of your time will now be spent with a small number of direct reports, so you’re no longer directly role modeling the behaviors you want to see in the organization as a whole in areas such as goal setting, feedback (positive and negative), quality bar, and prioritization.

The central challenge when selecting and managing leaders is ensuring that things are done the right way, even when you’re not looking.

Martin Mignot, Index Ventures

Find “executive-stage fit”

Very few functional leaders can be star performers at all stages of growth. Companies often progress through multiple generations of leadership in core roles on their journey from startup to IPO-readiness. This can be challenging to manage as a founder, since it can involve letting go of executives as well as finding new ones— topics we’ll address later in the chapter.

We can distinguish three leader personas that map against stages of a company’s life: Builders, Scalers, and Optimizers. Each of these personas also brings a distinct blend of leadership thinking: strategic, tactical, and operational.

1st Generation—Builders excel at reasoning from first-principles to quickly spin up a function from nothing. As multi-tasking player-coaches, they thrive in ambiguity.
Title / Level = “Head of” or Director
Core skill set = Tactical + Operational

2nd Generation—Scalers are skilled at templating ways of doing things at scale. They’re seasoned managers, and demonstrate strong potential, if not first-hand experience, of being effective managers of managers.
Title/Level = VP or CXO
Core skill set = Strategic + Tactical

3rd Generation—Optimizers have worked at large corporations. They know how to lead big, multi-disciplinary, matrixed organizations that connect across multiple geographies and business units. They’re experienced “leaders of leaders”. While they can add value post-IPO, they’re rarely helpful in a pre-IPO company. In fact, their process-heavy mindset can be destructive in high-growth.
Title/Level = CXO
Core skill set = Strategic + Operational

As a functional team gets bigger, you move from generalists to specialists, and then to segmented sub-teams. It takes a more experienced leader to execute effectively across all these pieces.

Abakar Saidov, CEO & Co-Founder, Beamery

The point at which these types of leaders come into their own varies by function. Headcount is one key factor. Since engineering and sales teams tend to be the largest, the need to switch from “doing to managing” and then to “managing managers” tends to happen here first. This is reflected in our analysis below. But other factors also contribute. For example, as you prepare for an IPO, you need a CFO and General Counsel who have the credibility and gravitas to reassure institutional investors.

HOW MANY SEPARATE LEADERS DO COMPANIES CYCLE THROUGH ON THE ROAD TO IPO-SCALE? HOW MANY SEPARATE LEADERS DO COMPANIES CYCLE THROUGH ON THE ROAD TO IPO-SCALE?

If you hire the wrong type of leader for your stage, expect things to go wrong, even for individuals with exceptional track records and pedigrees. Scalers will struggle to hire and inspire the caliber of people needed for them to step-up to be Optimizers. And Optimizers will struggle to get into the weeds and lead by example, which is necessary as a Builder.

While the functional teams that experience most growth are the most likely to need transitions in leadership, the tenure of different functional executives illustrates the different dynamics at play. The longest tenured executives are in Finance, Engineering and Legal, while the shortest-tenured are in People/HR, followed by Sales. This aligns with our experience—Finance and Engineering Leaders have more objective and tangible skills and qualifications. By contrast, leadership of the People function is more subjective and intangible, and depends upon a close match between the values and behavior of the People Leader and the CEO. Sales leadership has very measurable objectives, but performance shortcomings show up quickly, and the area can be prone to a mercenary mentality.

average executive tenure average executive tenure

Can people move between the Builder, Scaler and Optimizer leadership styles? Sometimes you’ll find leaders who excel at one of the earlier stages, and who go on to specialize as serial operators at that specific phase in the startup lifecycle. You can also find leaders with less experience who can continue to thrive in leading a function, even in hyper-growth. Conversely, you’ll sometimes find a leader with huge amounts of experience and maturity who is able and motivated to step back from Scaler to Builder, or (more rarely), from Optimizer to Scaler. But it’s vanishingly rare for a successful double step-back from an Optimizer to a Builder.

I’ve had more positive surprises from people hired for more immediate needs who are able to scale into the future than the opposite. Hiring big company Optimizers rarely works for pre-IPO businesses.

Martin Mignot, Index Ventures

Calibrate what excellence means for each executive role

You should be regularly discussing the performance and evolution of your leadership team with your Board, your advisors and your coach (if you have one). This will give you a sharper focus on emerging gaps, and allow you to plan in advance for hiring, or switching out, executives.

Where you suspect gaps are emerging in a leader’s ability to perform, you should begin a process of external calibration. Leverage your investors, network and search partners so that you can talk to top outside executives in that area. These don’t need to be interviews with active candidates, but they should be conversations that you prepare for, to reframe your expectations of what “great” looks like for your stage of growth.

We’ve used board members and our VC’s Talent teams for introductions to both active and calibration candidates.

Assaf Rappaport, CEO & Co-Founder, Wiz

Executive hiring calls for a different mindset from you as a founder. Candidates will be deeply knowledgeable about their area and are likely to have longer career histories than yourself. But don’t be bowled over by an amazing resume, and trust your intelligence. If a candidate can’t explain something clearly to you, it’s more likely to be a problem with them than with you.

You’re constantly upskilling across the board, and it can be hard to balance trusting your gut with the rigor that’s required to find your second gear.

Alex Zaccaria, CEO & Co-Founder, Linktree

I made some poor executive hires early on. But I learned from that and got better. I just had to. I came to know more clearly what I was looking for, and was willing to wait for months and months without caving in to the pressure to compromise.

Andrew Robb, COO (former), Farfetch

LEADERSHIP PERFORMANCE GRID LEADERSHIP PERFORMANCE GRID

Build towards a full-stack leadership team

The following executives are critical leadership roles common to any IPO-ready successful tech company, regardless of its focus or how it operates. Additional executive roles may be critical for your specific sector or business model—for example, Chief Risk Officer or Chief Investment Officer in fintech, or Chief Supply Chain Officer in D2C.

The precise composition of your executive team, including the hiring pace, sequence and the mix of C-level and VP-level executives, should reflect your:

  • Stage of growth
  • Strategy and competitive differentiation
  • Strengths as CEO and the strengths of existing executives

Example 1—If you put design at the heart of your competitive differentiation (e.g. Airbnb or Squarespace), then having a Chief Creative Officer makes sense.

Example 2—If you have an exceptional early executive who really understands your broader strategy, you might make them COO, with several functions led by VPs below them.

It’s a meta-skill for any organization to periodically reorg in order to align its people with an evolving strategy.

Soleio, Investor × Designer, Figma Advisor and former Dropbox and Meta

You should steadily build your executive bench as you grow, but expect more rapid executive hiring between 125 and 500 headcount. This reflects growing operational intensity in the business. It’s often a particularly high-pressure period for you as CEO, because you’re personally managing emerging leadership gaps while also making time to hire into them.

AVERAGE NUMBER OF EXECUTIVES AT EACH HEADCOUNT STAGE AVERAGE NUMBER OF EXECUTIVES AT EACH HEADCOUNT STAGE

TeamPlan—Explore our entire library of 210 highly-successful startups for more detailed insights into when and how they built their leadership teams.

Hiring executives

Hire no more than two executives a year

Don’t hire a whole slate of executives at the same time. Finding and hiring exceptional executives is tough. Hiring several in a year, at the same time as maintaining your quality-bar, onboarding them successfully, and expecting business needs to stay roughly the same, are compounding risks. We suggest an annual limit of two new (CEO direct report) executives, and in exceptional cases, three. This will force you to think carefully about your priorities as you build your exec team.

Each year, you should bring on one exceptional (C-suite) executive. Someone you’d have been unable to land in previous years.

Dom Vidal, Index Ventures (former)

I tried hiring four executives at the same time last year, but it was unsustainable. One is ideal, and the absolute max is two. Never do more.

Matt Schulman, CEO & Founder, Pave

Reframe your perspective on interviewing—Jason Citron, CEO & Co-Founder, Discord

Spending the time to recruit executives and senior people is critical as you grow. Bringing in individuals who’ve “seen the movie before” creates the leverage you need. But I was held back because I just found the endless hiring processes and interviews boring. It was like eating broccoli. It wasn’t until I reframed my approach to ask, “What can I learn from this person?” I now treat interviews as advice sessions. I ask people to help me work through relevant current issues. It’s a great way to assess them and is also stimulating for me—it’s like adding garlic and chili flakes to help the broccoli go down!

Hire executives aligned with your needs in two years' time

You need to reframe what capabilities you need from an executive hire against what your company will look like in 18 months to three years’ time, not against your needs today. The faster your growth, the more important, and challenging, this is to envision. However, it’s essential so that your ramped executive can operate at their sweet spot of experience, but also look forward to new challenges beyond. This also gives you the time as a team to hit the milestones necessary for the executive to be successful—for example, to get your product ready for rollout by a new enterprise-focused Chief Revenue Officer (CRO), or to put in place the necessary accounting foundations that a strategic CFO can build upon.

Hire leaders for your next chapter of growth, rather than on a timeline. If you’re preparing to roll out an enterprise offering, hire a CRO or VP Sales capable of doing that.

Nina Achadjian, Index Ventures

I optimize for the job as I envisage it in three years’ time. Most people run in cycles, where Y1 is onboarding, Y2 is performing, and Y3 is getting itchy about what comes next.

Andrew Robb, COO (former), Farfetch

There are times you just need to hire someone to get you through the next two years, even though you suspect they’ll then plateau. You can think of this as a ‘tour of duty’ approach, and reassess what you need when their tour is up. In general, though, you should try to hire someone you can imagine being in the seat in three years’ time, particularly in roles that you expect to look very different then versus now.

Sandra Schwarzer, Index Ventures

Look for “step-up” execs

To widen the pool, consider a candidate looking for a step up. You’ll want to look for someone who has thrived in a second-in-command role, running a function at a similar or later stage, and who’s had a great mentor to learn what excellence looks like. Their current job title or the number of people they’ve managed isn’t nearly as important as having skills equivalent to a proven leader (e.g. communicating, influencing, inspiring, developing, handling complexity). However, be more cautious about step-up candidates for execution-intensive roles running big teams such as Sales or Engineering. In these cases, you want someone who already knows what to do.

Don’t only look at executive experience. Also look for the number two who wants to become number one. For example, a Finance Leader who’s lived it all including an IPO, but didn’t lead it themselves. These people are hungry and can grow.

Assaf Rappaport, CEO & Co-Founder, Wiz

Think hard about how far you can broaden your search to include candidates working in different sectors or business models. For some roles, you might be looking for very specific sector insight and experience, such as enterprise security sales. But for others, like CFO or VP People, you can flex more widely, which in turn improves your candidate diversity.

Location also has a big impact on your access to talent. The Bay Area still has by far the deepest pools of executive tech talent across all roles. This will shrink significantly if you are in a nexttier location such as New York, LA, Boston or London, and dramatically for most other places. Think through whether relocation would be necessary for the right candidate, or how much in-person travel time would be acceptable. Otherwise, manage down your expectations on hiring proven executives, and focus on step-up hires.

Consider the impact on your incumbents

If you need to hire on top of an existing leader, be sensitive. Figure out if it’s better to try to hold onto the incumbent, or to encourage them to move on. If you want to keep them, present it as an opportunity, and make sure the incoming exec is truly a step-change, someone they can respect and learn from. Make the transition a success for your incumbent leader, opening their path to be a step-up candidate in a future role.

If you want the incumbent leader to stay on with you, it’s really important to involve them in the interview process, though only later, once you’re reasonably confident that you’ll make an offer to the candidate. The incumbent shouldn’t have a right to veto, but they might flag potential issues. The interaction should ideally be in the context of a case study or lunch, rather than a formal interview or competency assessment. You should do a rich debrief with the incumbent to draw out potential onboard ing opportunities or challenges for both the candidate and the existing leader.

Sandra Schwarzer, Index Ventures

Look inside and out for executives

We discussed why internal promotion is a good idea in the last chapter, and how it needs to be balanced against the benefits of drawing in fresh perspectives and candidates with richer operating experience. These challenges bite the most at the executive level, which is reflected in the range of opinions offered below. In high-growth, you’ll need to look externally for the vast majority of executive-level appointments. On the other hand, the proportion of executives promoted from within will increase with scale. Our analysis indicates that 18% of executive appointments made between 51–125 total headcount are the result of internal promotions, rising to 25% between 126–500, and reaching 32% by 501– 1,000. We also found that internal promotions to VP level are twice as likely (20% of total) as those to CXO (9%).

PERCENTAGE OF EXECUTIVE APPOINTMENTS MADE AT EACH HEADCOUNT STAGE THAT ARE INTERNAL (%) PERCENTAGE OF EXECUTIVE APPOINTMENTS MADE AT EACH HEADCOUNT STAGE THAT ARE INTERNAL (%)

Why you should hire externally

There’s a tendency, especially for first-time founders, to be too loyal to their existing team leads and too trusting in their ability to scale. Instead, there needs to be an honest reckoning: Are the people leading the company today really the right people to take you to the next stage? If a skill set or expertise you need is missing, you need to find it externally.

Sian Keane, Chief People Officer, Farfetch

You go through so much together with your early leaders. You want them to continue to succeed, and it’s hard to take your loyalty out of the equation. You can end up putting their needs ahead of the company’s.

Anonymous Founder

If your year-over-year growth goal is 35%, you can probably promote internally, if your existing team is working like clockwork. But 80% or 100%? That’s just not possible without people falling over. You need to supplement your leadership with external talent to cope with that pace of change.” Marcia Kilgore, Founder, Beauty Pie “External talent can raise the bar, and expands the skill set and perspective of your team.

David Lee, Chief Creative Officer, Squarespace

The toughest decisions involve internal candidates with great potential, but where you just don’t have the time to wait for them to get there. It doesn’t happen often, but when it does, it hurts.

Andrew Robb, COO (former), Farfetch

Our first CX agent was amazing and ambitious, but not highly experienced. We progressed her too far, too fast, and without sufficient mentoring. Eventually, with a team of 150 under her, the pressure became too much. We made a mistake, which I’ve tried to learn from.

Anonymous Founder

Why you should promote internally

The state-of-the-art isn’t what’s going on in the last generation of post-IPO tech companies. If you’re super successful, it’s a new playbook, likely written at your company!

Soleio, Designer × Investor, Figma Advisor and former Dropbox and Meta

It’s human nature to look for superstars outside. We undervalue the people we know, and overvalue the people we don’t.

Kipp Bodnar, CMO, Hubspot

Internal promotion is particularly important from a diversity and inclusion perspective—identify and nurture your own talent pipeline.

Lindsay Grenawalt, Chief People Officer, Cockroach Labs

It’s controversial to say, but some functions have such a mediocre executive talent pool—in marketing and people in particular—that it’s often not worth bringing in a so-called expert from outside.

Anonymous

Each external executive hire you make involves a risk. It can go horribly wrong, even with a rigorous search process.

Sian Keane, Chief People Officer, Farfetch

Stability and equilibrium are often undervalued in leadership, versus bringing in new leaders externally.

Gabriel Hubert, Co-Founder, Dust and Product Lead (former), Alan

Also be aware that some investors can have a tendency to look to a big hitter from the outside to solve problems. But bear in mind that they won’t know your own team members and their strengths as well as you do.

Scaling yourself in a scaling company— tips from Farfetch

Sian Keane joined Farfetch in 2013 as Head of HR when the company had 60 employees. She was promoted as the business scaled, becoming Chief People Officer in 2018 and through IPO. She offers three lessons for professional development:

1. Network—Build a solid group of external professionals who knows what challenges are likely to come in the next phase of growth. It’s critical to know what’s coming down the track in order to plan and be ready for them.

2. Think longer term—Major processes or projects can take a year to design and implement, and another year to embed. So you need to project forward two to three years, to design for what the organization will have grown into at that point, and therefore what will be needed. You need to turn this type of thinking into a habit.

3. Invest in your personal development —Set aside a generous amount of time for coaching, reading and courses. Actively seek out feedback, and be open to changing as a result of what you hear. Cultivate humility and self-awareness.

Having a growth mindset is key to scaling as an executive in a high-growth company. Embrace imposter syndrome, with a thirst to learn and stretch yourself. Push constantly to be better. But demand brutal honesty from the CEO to tell you if they think you’re falling behind. You’re a shareholder too.

Nina Achadjian, Index Ventures

Run rigorous executive search processes

If you need to prioritize an executive hire, and there’s no amazing candidate either internally or uncovered through your network, then you should work with an external search partner.

Given the air of mystery that can surround headhunters and executive search, it’s worth going into more detail for exactly how to do this, using our 13-step process below.

1. Be judicious about who you pick

Founders often don’t pay enough attention to this critical first step. Get recommendations for search specialists from your network and your investors. Get pitches from two or three, and be sure to take references from recent clients. Make sure you ask plenty of questions, such as:

  • Have you done similar searches to this one before? When?
  • Who ran these searches? Are those individuals available to work on my search?
  • How well do you understand this type of role? Can you describe specific candidate archetypes and which might be right (or not) for us?
  • What success have you had in securing diverse hires for your clients? How have you achieved this?
  • Which companies are off-limits due to client clashes?
  • How many searches will your lead partner be conducting in parallel?
  • Are you conducting parallel searches which might create tension or conflict due to an overlap of potential candidates?
  • Who will make the first call to candidates? Who will conduct the first interview?
  • Can you provide sample profiles based on our first (pre-selection) call? (This is to check how well they have understood your brief.)
  • Can you show us you understand the compensation range for this role, split between proven versus step-up candidates?
  • Can you provide constructive challenges to our objectives? For example, in relation to our access to top candidates, who can we realistically target given our stage and profile? Are our timeframes for completing this search realistic?

Fixed-fee is the standard approach, split into three staged tranches (kickoff, mid-way, and getting an accepted offer from your chosen candidate). Some top firms have an appetite for taking equity in lieu of cash for a portion of their fee, although very few will push this.

2. Be clear about your priorities

Your search partner should take the lead to ensure that you:

  • Know the likely overall timeline for the search, and when you can expect to be meeting the first pre-screened candidates.
  • Map out the full hiring process in advance: Which interviewers, in what sequence, and with what power (influencer versus veto-power)?
  • Write a job description, which can be shared with interested and vetted candidates.
  • Build a scorecard for the role, setting out the four to six key competencies you’re looking for, potentially with a weighting between them.
  • Establish “candidate archetypes” that may be a good fit and worth targeting. For example, you might define three archetypes as: proven candidates in your sector, proven candidates in adjacent sectors, and step-up candidates in your sector.
  • Set diversity goals for the search. Your search partner should be able to let you know the key diversity parameters for the specific role, allowing you to realistically target a specified percentage of diverse candidates for initial conversations, and for your shortlist.
  • Share the above materials with your interviewers, and ensure alignment.

Get the recruiter to pitch the role back to you, before they start outreach to candidates. This is to make sure they’ve got the story clear, and can effectively showcase your company, the role and the opportunity.

3. Stay abreast of the search process

  • Schedule weekly update calls with your search partner to discuss specific candidates, the overall candidate pipeline, and any feedback they’re hearing back from the talent pool overall. Do not delegate these calls—as CEO you need to be driving the process.
  • Conduct initial meetings with a slate of candidates that cover your target candidate archetypes to help you sharpen your preferences and narrow the search parameters.
  • Highlight top (and top diverse) candidates, where initial outreach could be directly from yourself to improve the likelihood of a response.

4. Start interviewing within two months

There’s a wide time range for running a search from kickoff to an accepted offer. It can run from as little as six weeks to as long as seven to eight months for highly complex searches (e.g. a tricky role in a tough geography with specific diversity requirements). However, you should be meeting multiple viable candidates within two months, and have established a clear understanding of what “great” looks like.

5. Use your interview time efficiently

Getting your leadership team in place is a key priority. Great founders will make time for candidate calls without slowing down the overall search process. On the other hand, you shouldn’t need to speak to 20 candidates. Your search partner should ensure that each interview you conduct teaches you something new, even if you reject the specific candidate.

6. Engage passive candidates

The majority of candidates you’re likely to meet during a search will be passive. Although the search firm will have warmed them up, you’ll need to spend five to 10 minutes connecting with them on a personal level before you can gauge how much effort it will take to sell the opportunity to them and get them fully invested in the process. Only then will you have earned the right to quiz and assess them at length.

7. Have an open dialogue with your search partner

When issues arise, the key is to have an open and ongoing dialogue with your search partner. They should know if you’re unhappy rather than being surprised if you express disappointment after several weeks. Likewise they should be managing your expectations about the search process and target candidates, ensuring you’re all aligned and that their assertions are supported with data. For example, if they say that you are overly focused on aspirational versus viable candidates, can they prove unresponsiveness to outreach or compensation expectations that are beyond your budget?

Here are some of the main reasons why executive searches go wrong:

  • A mismatch between the search partner and the client on the exact role or profile you’re looking for—This suggests poor stakeholder management by the search partner.
  • Clarity of feedback—Are you giving clear feedback after each interview you conduct to help the search partner tighten their parameters? Or are they failing to adjust their approach based on your feedback?
  • Lack of success connecting with target candidates—For example, is your search partner over-committed and using juniors to call candidates who are unable to convey your story effectively?
  • Lack of internal alignment—Do your interviewers have a shared understanding of what you’re looking for?
  • Time-lags between interviews—Are you moving candidates through the process fast enough or are you losing them to competing searches or to a sense that they’re not a priority?
  • Reputation in the market—Have you pre-burnt yourself in the market through negative news or opinions shared by former employees?
  • Hot talent market—We’re past the craziness of 2020-21, but top candidates remain in very high demand. A hot talent market can still make a search twice as hard and long, with candidates fatigued through constant approaches by recruiters.
  • Rigidity about location—If you’re not in a top-tier location and insisting on permanent relocation, you may simply be unable to find candidates willing to engage in your process.

8. Assess candidates’ technical skills with an outside expert

As we discussed in Chapter 4, it’s good to apply the same questions to all candidates so you can easily compare their responses. In addition to what we’ve covered previously, use the scorecard you’ve created with your recruiter as the basis for the questions.

For many executive roles, you’ll lack individuals internally who can really assess a candidate’s technical skills. In this case, involve an outside expert to conduct a purely technical assessment. Your investors should be able to introduce relevant experts for most functions.

Dylan [the founder of Figma] is exceptionally good at seeking outside advice from experts to learn about new topics. He recognizes the limits of his own knowledge.

Amanda Kleha, Chief Customer Officer, Figma

You need a very bought-in candidate before you can use a complex case study requiring hours of preparation. Otherwise, you’re giving candidates an excuse to pull out of the process entirely. This means that the case study is usually the last step in the process before you extend an offer. Also gauge the candidate’s situation—for example, a CFO at a sensitive point in their budgeting or fundraising cycle isn’t going to appreciate the extra burden.

9. Make sure candidates’ values align

In an executive hire, values-fit is crucial. In addition to the suggestions we offered in Chapter 4, you’ll need to invest extra time with candidates you’re assessing for your executive team, so make the most of it. Once they’re deep into the process, you want to observe them carefully in-person, both in and out of the office. How do they interact with other people? What does this say about their values? This is also an opportunity to gauge your personal chemistry, which is critical with any direct report that you hire. You have to be able to relate to the individual, have a good rapport, and find your interactions with them enlightening and energizing. But you also have to be aware of unconscious bias, and the tendency to hire people who look, sound and think like you, or what you understand “competence” to mean.

With candidates from very large organizations, try to anti-sell them in the interview. Really push at their motivation. It’s a risk, but candidates who haven’t actually worked in a startup can be drawn to the romance rather than the reality, and end up leaving.

Andrew Robb, COO (former), Farfetch

One of the simplest tests is taking someone for coffee or lunch, and seeing how they treat the barista or server. It sounds straightforward, but it’s amazing how many people can regurgitate values from a job spec in a discussion, but clearly not live them in practice.

Charlotte Howard, Index Ventures

As soon as possible after each interview, complete a scorecard for the candidate. Highlight points of interest or concern against each competency and areas for follow-up, if the candidate made the cut to progress to the next stage. Also think about which of your internal interviewers will be best placed to explore each of the outstanding areas.

Any instinct you have from interviewing is probably right, and 10× worse than you think it is. Take time to lean into the feeling and unpack it. If you perceive a lack of fit, don’t move forward.

Max Klijnstra, Co-Founder and Chief Growth Officer, Otrium

10. Get feedback from interviewers

Ultimately you are the hiring manager, and you can’t delegate the decision. But you want to get objective and frank feedback from your other internal interviewers. Use your scorecard to focus this feedback on what really matters.

Make sure that you don’t bias other interviewers by providing too strong an opinion about how you feel. Collect the feedback “blind” as soon as possible after they have met the candidate.

If you’re deciding as a group on whether a candidate should receive an offer, the CEO should always speak last, to avoid introducing bias.

Sandra Schwarzer, Index Ventures

11. Take at least four references

Eliciting representative references to guide your decision-making is particularly significant when you’re hiring executives. (See our earlier remarks in Chapter 4 for some background about how to handle references and backchannel checks). You should aim for at least four references for any executive hire, and ensure you collect broad feedback (previous managers, peers, and subordinates) to give you confidence about your decision, and also to identify insights to help with effective and personalized onboarding.

I do loads of referencing on executive candidates, sometimes up to a dozen. There’s no such thing as too much.

Amit Bendov, CEO & Co-Founder, Gong

12. Make your offers personal

As the CEO, you should always extend your offer verbally one-on-one to an executive candidate. Make it as personal and authentic as possible, highlighting why you’re looking forward to working together and the scale of the opportunity this role affords. Follow up with a written offer letter that restates why you’re excited by them, and why you think they should be energized by this opportunity.

Index Ventures’ Rewarding Talent offers further guidance around equity compensation for executive hires.

Obtain board (or Remco) approval before you table any executive offer, including upper limits for how far you’re willing to step up during negotiations. If the candidate is going to see a drop in their cash compensation, you might choose to table your highest and best offer upfront. Alternatively, you might give yourself some wiggle room by starting lower.

Compensation negotiations with executives should never go for more than two rounds, otherwise they corrode good faith and mutual respect.

Dominic Jacquesson, Index Ventures

You need to be prepared for a candidate to reject your best offer. This can be tough after you’ve invested so much time in building conviction and internal alignment, but offer acceptances for executive roles are 75–80%. You need to be ready to walk away and continue your search. But you should first explore in detail with the candidate why they’re saying “no”, in case there are elements that can be worked through. As one example, is it a question of start date versus a significant vesting point in the candidate’s current role?

13. Spend the first year onboarding

Several of the entrepreneurs we spoke to confessed to hiring excellent executives who failed to make their expected impact, primarily because of insufficient or poor onboarding. These executives never learned how to navigate the organization effectively or to understand the context behind historical decisions, and therefore failed to build trusted relationships with the people that really mattered. They usually ended up leaving the organization and the whole executive hiring process had to restart, this time with the added challenge of having to explain to wary new candidates why the previous incumbent didn’t stick around.

Poor onboarding is often the cause of executive hires rapidly bouncing out. Give up any machismo ideas about ‘sink or swim’ or throwing people in at the deep end. You want them to have a positive impact as soon as possible, so invest upfront and set them up for success.

Sandra Schwarzer, Index Ventures

For executives, onboarding is not a 90 day process—that’s just too short. Their whole first year can be considered part of onboarding learning the culture, building critical relationships, understanding systems and so forth. Be deliberate about creating a plan. You need to spend enough time with the executive both inside and outside work to establish trust and openness.

Onboarding will involve a range of other people too, both internally (e.g. peers) and externally (e.g. customers, vendors, investors). You should jointly define and prioritize whom they should spend time with, provide pre-briefing context, and spend time debriefing. Focus on early warning signs come up during this period, such as misunderstandings or ambiguities that could impede effectiveness, and unpack why they arose. For example, role overlaps or differences in communication styles or personalities. In particular, watch how they respond to feedback, particularly to criticism. Remember that while people can change their style or approach, there’s zero chance of this happening unless someone has explained why that style isn’t appropriate in your company, and how they should behave instead.

I recommend daily 15 minute one-to-ones with direct reports during onboarding. Keep this going until it becomes obviously over-the-top. Inadequate onboarding can be fatal for a new executive. You need to give immediate feedback to set them up successfully. I also go above and beyond in stressing to my direct reports the need to be raw in their feedback to me. You’ve got to establish honesty and openness in all your communications.

Matt Schulman, CEO & Founder, Pave

You can add further richness and evidence into feedback you offer to executives by personally conducting 360s with their direct reports at the six and 12 month points. As CEO, people might find it hard to open up to you with negative comments, fearing that you could disclose what they share in a way that could come back to bite them. If you have cause for concern, you need to ask direct reports who you know to be high performers about the specific concern, and stay attuned to subtle signals when they respond, so that you can lean into this for more detail.

The first 90 days is also a unique opportunity to leverage a new executive’s fresh pair of eyes on the business. Make the most of this time for “reverse onboarding” to hear what the new hire has to say in order to identify strengths and weaknesses in your own company and team.

Fire under-performing executives decisively but graciously

Even with a thorough assessment and onboarding process, you can’t guarantee that executive hires will work out. For a start, there’s a learning curve to figuring these processes out, so expect to make at least one or two executive mis-hires as you build out your team, and don’t beat yourself up for having made a mistake. As discussed earlier, only a minority of executives can adapt their approach across multiple stages of company growth, which means that the time will likely come when you part ways with them.

In the early days, I was too slow to pull the trigger on under-performance. One of my first hires took me 12 months to let them go. The next was six months, then three, and then two. I’m getting better at identifying issues and acting on them.

Anonymous Founder

This can be emotionally tough. You know how challenging and disruptive it will be to hire and onboard an alternative executive. But you need to stay alert to signals, particularly during their first six months, that things aren’t working out positively. A consistent failure to hit mutually agreed objectives is a clear signal, as is a failure to course-correct on behavioral issues that you’ve flagged to them. Repeated negative feedback from 360 reviews conducted with the executive’s direct reports is another. If these indicators mount up, you should share your concerns with two or three trusted confidants to get their perspectives: board members, established senior executives, co-founders or relevant advisors.

Be very wary if an incoming executive starts to lose, or to fire, individuals below them who you had thought were high-performers.

Mark Fiorentino, Index Ventures

Where you get clear signs that things are going wrong, and where direct feedback and guidance has failed to bring things back on track, you need to be decisive in removing them. Otherwise things will inevitably get worse over time. You will suffer poor motivation and potentially lose valuable team members, making it less likely that you’ll meet your business objectives. Failing to act could also undermine your team’s confidence in you as a leader, since you’re the only person who can put things right.

I had an excellent early ops hire, who was smart and strategic. I promoted him to be a manager, and then to VP—this involved managing managers, which he hadn’t done before. When a VP Sales hire didn’t work out, I asked him to step in as I was over-stretched. The wheels started to come off at that point. It took me a while to establish that the issue was more than one of over-stretch or burnout. He just wasn’t able to develop his management skills in step with the scaling in his teams. When he started to lose good people, I was forced to act. It was emotionally tough, but we just couldn’t afford to slow down our pace for him to catch up.

Anonymous Founder

At this point, if you haven’t already, you’ll need to disclose your decision to your People Leader, so that you can jointly orchestrate a termination process that doesn’t expose the company to risk.³ When it comes to the actual meeting with the executive, you need to take care to follow all guidelines, particularly outside of the US, where employee protections tend to be stricter.

³ It is also recommended to have the exit package and documentation reviewed by an employment attorney.

Know what you’ll have to cover in the meeting, including:

  • The timeframe for departure
  • The status of any final/severance pay due and benefits (particularly health cover)
  • What you expect from them, if anything, in terms of handover
  • The status of any accrued bonus or exercise rights over vested stock options

These points should also be written up and printed for the individual to take with them to review more calmly afterward.

The best advice I was given before holding my first termination meeting was to rehearse these lines to use to kick off the meeting: “I’m afraid I don’t have good news to share with you today. We have decided to let you go from the company.” Make sure you can say this while maintaining eye contact, and conveying a neutral but human tone. Pause afterward to hear the reaction. Expect that this may take an uncomfortably long time, as the person processes the news. Be compassionate to the fact that you are telling them that you have lost faith in them. I’ve followed this advice with each termination I’ve had to conduct since.

Anonymous Founder

If you have been clear in previous feedback to the individual regarding your mounting concerns, the news of their termination should not come as a surprise. For the majority of people in this case, their reaction will primarily be one of sadness. They might ask how you came to this conclusion, and you need to be prepared with what you will say, as a succinct but direct summary.

Depending on personality, their relationship and their own assessment of what’s led to this point, some people can assume a sense of cynical acceptance, which you need to have the composure and maturity to let pass. Only a small minority of individuals respond aggressively, and you should be able to gauge in advance whether this is a possibility. If they do, you need to bring the meeting to a conclusion quickly. Maintain calm, saying, “I’m sorry that you feel this way, but I considered this decision very carefully, and it is final.”

Regardless of how an individual responds during the termination meeting itself, in the period following it and leading up to their final day, most people do become more negative and cynical. They may also become outspoken in their criticisms of you and of the company. In these cases, if you had expected the individual to continue working during their notice period, you should consider switching them to paid administrative leave.

You also need to restrict or remove access to any company information, systems and premises following the meeting. Even if the individual handles the termination news with good grace, you should apply certain restrictions during their notice period. At the least, you should closely monitor their access and file download activity to protect sensitive data and knowledge.

Co-founder Relationships

Should co-founders stay or go?

Co-founder harmony is critical to the early success of any startup. However, while a large majority of founding CEOs retain this position in successful companies through to IPO or exit, only a minority of co-founders retain an executive role through to IPO. In fact, many end up leaving the company prior to exit.

PERCENTAGE OF FOUNDERS STILL WORKING AT THEIR COMPANY BY HEADCOUNT STAGE PERCENTAGE OF FOUNDERS STILL WORKING AT THEIR COMPANY BY HEADCOUNT STAGE

The principal reason for co-founders stepping back or out is that they lack the skill set or desire to build and lead a large team. In these cases, there might be an alternative and mutually-beneficial role for them within the company, such as being an individual contributor or leading a subteam or initiative. However, many co-founders choose to step away entirely. They might prefer a return to an earlier-stage environment, or they might wish to start a new company, or pursue entirely different career or personal goals.

These transitions can be hard for you and other co-founders to navigate. Hopefully you’ll both end up on the same page, making the transition a bittersweet but positive experience. You might benefit from the input of a mutually trusted advisor or board member in preparation for such a conversation. But ultimately, as CEO, you have to find a solution that is in the best interests of the company.

The same advice applies to yourself, if you feel joyless or unable to cope at the thought of leading the company through the next set of goals and challenges. This isn’t a character flaw or failure. Rather, it’s a mature and brave acceptance. While investors undoubtedly prefer founder-CEOs, they also know that this isn’t always in the best interests of either the company or the founder.

We were looking to close a seasoned executive. I knew she’d only accept a C-level title, reporting directly to me. This forced a difficult conversation and rapid transition with my co-founder. Ultimately he realized what was best for the company and agreed to work under her. It has been transformational for both the company and for my co-founder.

Anonymous Founder

We realized over time that whereas I got joy from the outcomes—regardless of what tasks this required me to actually do— my co-founder’s joy had come from crafting and coding the product, rather than the stuff that they now had to do at scale.

Anonymous Founder

CEO Leverage

Limit your direct reports

There’s no “magic number” in terms of CEO direct reports. Multiple factors can influence the best solution: stage of growth, business model, founder DNA, and the capabilities of the specific leaders in the company. Reporting lines can also be fundamentally reconfigured if a COO is appointed who can take over direct responsibility for a large chunk of the organization.

In the earlier stages of the company’s life, CEOs often have a large number of direct re ports—say 10 or 12—as there’s simply a lack of alternative options. This is particularly true for solo founders and represents one of the toughest challenges of taking that path. It’s vital to build CEO leverage by establishing appropriate support, as well as by hiring leaders to whom you can delegate.

With scale, the CEO role involves more intensive external-facing responsibilities. You need to spend more time with investors, media, key customers and partners. Your number of direct reports needs to drop accordingly. Note that direct reports in this context don’t include individuals whose role is explicitly designed to provide CEO leverage, such as an EA or Chief of Staff.

By 500 headcount, we advise that a CEO should not have more than eight direct reports, and it could be as few as three.

The following functional leaders are direct reports to the CEO by the 500 headcount stage:

  • COO/President
  • Finance—CFO or VP Finance
  • Technical—Chief Product and Technology Officer (CPTO) or a separate CTO/VP Engineering and VP Product
  • GTM—Sales (CRO or VP Sales) and Marketing (CMO or VP Marketing)
  • People—Chief People Officer or VP People
  • Legal—General Counsel

Without careful attention (and a degree of luck), getting to this point might involve a particularly intensive “crunch” period between 126 and 250 headcount, when operational complexity is ramping up, but before you’ve been able to build out an effective bench of executives.

This situation isn’t healthy for multiple reasons:

  • It over-extends the CEO, drawing them away from critical engagement with product, the board and external communications.
  • The CEO will be unable to provide sufficient bandwidth to each functional area, either slowing things down or reducing the quality of decisions.
  • A CEO can’t be expected to be an expert in all functional areas, particularly as complexity increases, which further reduces the quality of decisions.
  • If the situation persists it can lead to CEO burnout.
  • It can make changes to reporting lines tougher when a new executive is hired.
  • Individuals may feel that it’s a demotion to no longer be directly reporting to the CEO

You should also consider lightening your load as CEO by temporarily giving additional responsibilities to trusted existing senior executives, even if those jobs are outside of their core competencies. If they have smarts, internal credibility and your trust, they should be able to rise to the challenge for a period of time.

More senior leaders bring a stronger focus on their own priorities and ways of working. The CFO is focused on keeping within budget. The GC and HR executive have a focus on risk. The CRO is focused on growth. This can lead to tensions. My job as CEO isn’t to play parent but to state clearly what I want our risk appetite to be and to communicate this clearly. I use live instances to demonstrate this. Then I need to step back and let my executives work it out between themselves.

Anonymous Founder

Consider a Chief Operating Officer

COOs play a special role in a leadership team, so it’s worth unpacking what they do, and whether it makes sense for you to hire one. It all starts with the founder. Are you at your best when you’re more hands-off from day-to-day operations, and can focus on vision, strategy and external audiences? Or are you better suited to running the business, setting objectives and holding people to account? If the former sounds like you, then a COO could unlock huge leverage.

There are a number of models for a successful COO. But regardless of what the role looks like, COOs are typically accepted as being a deputy to the CEO, empowered to make proxy decisions regarding almost any aspect of the business. It’s important to distinguish this framing of COO—as Chief Operating Officer—from the more narrowly defined Chief Operations Officer, which is about specific responsibility across Operations teams (such as supply chain activities in a D2C E-commerce business).

COOs are more common in Marketplace and B2C App business models compared to SaaS. A CRO in a SaaS business may take on elements of the COO role, when they oversee the entire GTM/ Revenue team.

The COO offers the CEO a partnership— someone else who works ON the business rather than IN the business.

Divinia Knowles, The COO Coach

The classic framing is that the COO is internally facing while the CEO is externally facing.

Hannah Seal, Index Ventures

Effective COOs are servant-leaders. They may be quite introverted, but with enough personality and confidence to build great relationships across all stakeholders. The best setup is when they are complementary to a more extroverted CEO.

Divinia Knowles, The COO Coach

COOs generally hold more authority than any other executive in the company besides the CEO. This may be reflected in one of three distinct setups:

1. The COO has a large portion of the organization directly reporting to them. This setup makes sense if the CEO is finding it challenging to effectively manage their direct reports alongside all their other priorities. Before the COO is appointed, the CEO may have more than eight functional lead reports. With a COO (which in this form might also carry the President job title), the CEO’s reports could drop to as few as three— e.g. COO, CFO, plus maybe a CPTO or Chief People Officer (CPeO). Alternative configurations are also possible: for example, the COO might take on the Tech team, but not GTM responsibility. Or in a Marketplace, the COO might take responsibility for both demandand supply-side teams.

This configuration requires a very careful and explicit delineation of roles between CEO and COO, and of reporting lines, particularly because top executive hires are likely to insist on reporting to the CEO. If your COO is supposed to be “running the show” this can create a conflict. You will also need to adjust your respective roles over time as the business evolves. The COO will need to have demonstrably richer prior operating experience than anyone else, as this lies at the root of their authority.

Well-known examples of COOs with broad responsibilities across a company:
Facebook/Meta
Sheryl Sandberg ←→ Mark Zuckerberg
Google/Alphabet
Eric Schmidt ←→ Sergey Brin
Box
Dan Levin ←→ Aaron Levie
King
Stephane Kurgan ←→ Riccardo Zacconi

2. The COO has less direct responsibility over portions of the organization. In this formulation, the role is more about building connective tissue and scaffolding for the organization. The COO drives the operating cadence and principles, OKRs and execution. This type of COO may own just one full functional team, plus a smaller “cross-organization” team (e.g. BizOps, corporate development, or analytics), although they often end up with additional interim or project-based responsibilities. For example, integrating teams, systems and products following an acquisition; to stand in if another executive leaves unexpectedly; or if there’s a business area that requires a dramatic overhaul. This flavor of COO tends to work best when the individual was previously in a more focused executive role, and is promoted to be COO—the most common shift being from CFO to COO. As a new hire, it can be tough for this kind of COO to build a deep understanding of the business, and they therefore struggle to earn the respect of the leadership team in a timeframe that’s realistic for the model to work.

Jonas was the very first employee at Personio in 2016, joining as Customer Success Lead, but limited prior experience. He’s been a superstar, and was promoted to VPCS, more recently becoming COO. He has retained responsibility for CS and CX, and has also taken on analytics and operating cadence.

Martin Mignot, Index Ventures

3. The COO is hired early and has broad responsibilities across the company. They are likely to have solid prior operating experience, but typically much less than in the first configuration. As the company scales, their direct responsibilities narrow as specialized functional executives are hired. The COO might be left directly owning only a single function, but they still retain the more holistic responsibilities of the COO role. They accumulate a deep understanding of the business over time. The degree of trust they’ve built with the CEO and others is the source of their authority, rather than their formal span of control as reflected in the organizational chart.

I joined Farfetch at seed stage, doing everything that wasn’t related to fashion: growth marketing, tech product, operations, G&A and international expansion. Jose [founder & CEO] focused more externally: on supply, business development and investors. As we scaled to Series C and D and brought on other executives reporting directly to Jose, my role narrowed, although I had to jump back into running teams during transitions. Both preand post-IPO, I ended up commercially focused on the core marketplace. But I also owned M&A and had earned a sort of soft power internally to shape strategy.

Andrew Robb, COO (former), Farfetch

Consider a Chief of Staff

If you think that you have the ingredients to hold onto the full-stack CEO role without needing a COO, you risk becoming the major organizational bottleneck because you’re overseeing so many direct reports and areas of the business. You need to create leverage by delegating more of your to-do list.

In this situation, it’s becoming increasingly popular to hire a Chief of Staff (CoS). The main distinction between a CoS and a COO is in terms of experience and remit. The CoS rarely has any team of their own. They triage who you see and when, join you for most meetings or one-to-ones, and provide briefings on significant external meetings. Their overall role is to ensure that you can focus on priority areas and that your team follows through on them. For example:

  • ExCo weeklies and offsites—building the agenda, capturing and pursuing next steps
  • Creating materials for board meetings or offsites
  • Fundraising—pulling together presentations and preparing investor briefing notes
  • Operating cadence—orchestrating OKR processes

We distinguish three levels of CoS, which align broadly with the stage of business:

  • Early-stage (Seed)—Gives you an extra pair of hands to competently conduct research and analysis, which accelerates decision making. Typically two to three years of prior experience.
  • Middle-stage (Series A–D)—Can execute on certain areas on your behalf, but mostly as coordinators. 4–8 years prior experience
  • Later-stage (Series D+)—Can execute with your authority (West Wing style). Deep experience, often including as a professional (e.g. legal or finance background). These tend to be career CoS’ers.
CHIEFS OF STAFF IN LATER STAGES TEND TO HAVE MORE EXPERIENCE CHIEFS OF STAFF IN LATER STAGES TEND TO HAVE MORE EXPERIENCE

The most common background for any CoS is either consulting, investment banking, law or VC. These are super smart, super focused and highly strategic individuals—hyper-organized generalists with exceptional intellect and drive. You should be punching above your weight to convince them to join at a particular stage. The quid pro quo is that they are desperate to get into the world of startups and work with a founder, but lack any obvious route in, so they are also willing to take a significant pay cut.

I have had a Chief of Staff (Guillaume) for five years now, since we were 100 people. He has given me huge leverage in execution: presentations, fundraising decks and tracking follow-up actions. As the company has matured I’ve been able to give chunks of this work to other leaders and I’m now thinking about reshaping the CoS role.

Rodolphe Ardant, CEO & Co-Founder, Spendesk

Typically CoS roles are “tour of duty” jobs lasting 18–30 months, after which individuals either take on another senior role in the company (e.g. General Manager of a business unit) or leave to pursue other opportunities. In exceptional cases where they have built credibility and respect, a CoS may also step up to a COO role.

Every founder should consider a CoS. It’s a brilliant way of bringing exceptional talent into your company.

Charlotte Howard, Index Ventures

Hire an EA

We recommend that all CEOs hire an EA by the time you hit 50 headcount. You can work with an EA at one of three levels, described below. Stepping-up between levels involves finding the right person, building trust and understanding, and also significantly adapting and delegating your own workflows, which requires an intentional shift in your mindset:

Level one

  • Calendar scheduling
  • Travel planning
  • Flagging key dates or meetings which require preparation
  • Helping on office management

Level two

  • Access to email—clear out junk and ghost-write responses as drafts for review
  • Tracking and feedback around how you’re spending your time versus your priorities
  • Anticipating what you might need or might have overlooked

Level three

  • Autopilot on email—permission to choose when to send stuff on your behalf
  • Identifying how the team operates—who’s upset and who should you spend time with
  • Responsibility for office cultural events
I hired an EA when Discord was 20 people and it was a big improvement. She funneled all meeting requests against my priorities, knowing when to schedule things.

Jason Citron, CEO & Co-Founder, Discord

I’ve now worked with my EA, Tina Long, for four years and Kalli White, my Chief of Staff, for seven years (though she had other roles within the organization in the earlier days). Thank God for them! Tina has also really supported me now that I’m a mother, helping me to organize school and childcare around work commitments. I have an A+ office of the CEO.

Kate Ryder, CEO & Founder, Maven

Curate your calendar

Set up color-coded blocks of time for thinking versus meetings (maybe split between internal and external), and for personal/family time. Audit this regularly and align with your priorities.

I timebox my calendar a lot, with blocks daily/weekly for workouts, email catch up, and thinking time. Mornings are for deep work. Meetings are between 10–5. Family time is 5–7, and 7–9 is US time [Abakar is based in London]. Twice a year, I also clear my calendar for a half day and ask myself, ‘If I was a professional CEO coming into the company right now, how and where would I be spending my time?’ I then restructure my calendar priorities accordingly.

Abakar Saidov, CEO & Co-Founder, Beamery

Jason Citron, Co-Founder & CEO of Discord, offers advice on prioritization

I’m a big fan of the Eisenhower Matrix. As a founder, whether you’re small or big, you need to free up time for the “important but not urgent” quadrant. Early on, you’re always being reactive, because there is just so much to get done simply to survive. But you need to get ahead of the game to avoid fires occurring in the first place. As you scale, there’ll be hundreds of people who really want to talk to you. It’s easy to become reactive to their priorities, which isn’t necessarily what’s best for the business overall.

THE EISENHOWER MATRIX THE EISENHOWER MATRIX

The judo move is to realize that other people’s sense of urgency can make things feel more urgent to you than they actually are. I think Reid Hoffman said it best, “You’ve got to let fires burn.”

I have introduced two techniques to drive my agenda:

  • A two hour block each morning when I’m at my highest energy to focus on my top goal. This way, I keep moving the most important ball down the field.
  • Regular block of “office hours” time for whoever internally needs to speak to me

Get a business coach

The majority of high-growth founders we work with have a business coach—someone to provide a safe environment in which to explore specific challenges, and to help them navigate their path to a solution. There are many different approaches to coaching, and a lot comes down to personal chemistry. However, it’s important to distinguish between a mentor and a coach. Mentors can provide the benefit of their technical knowledge, skills and experience, but generally on an ad hoc basis, and with less sharing about the emotional journey. Coaches offer active and regular guidance on your journey towards self-improvement, with full openness about the struggles that you may be going through. Some of the best coaches can also provide some active mentoring, but this is restricted to areas of specific prior operating experience.

Tap your network for recommendations and speak to several coaches before picking one. We recommend that your coach also spends time with your direct reports, and potentially with board members, so that they have a more rounded context, rather than relying purely on what you tell them.

In addition or as an alternative to a coach, find confidants and advisors outside the company with whom you can share your anxieties and problems. These could be family members or other founders.

I’ve had different coaches with each stage, and they have been critical for me.

Anonymous Founder

Beware of having a single role model whom you try to emulate. Diversity matters, so lean variously on coaches, mentors, peer founders, advisors, and board members as well as friends and family. Learn to align the right people for counsel on a given issue.

Hanno Renner, Co-Founder & CEO, Personio

I’ve developed a small but strong circle of entrepreneur friends in New York now. They ‘get it’. I used to have monthly dinners with two very good friends, Zach Sims from Codecademy and Liz Wessel from WayUp, over five years. We would talk about the good, the bad, and the ugly.

Kate Ryder, CEO & Founder, Maven

Look after yourself

It’s essential to take care of your physical and mental wellbeing. The stress and time-pressures of being a founder who is Scaling Through Chaos can be punishing. Remain mindful of your need for balanced nutrition, physical exercise and time to decompress. Consider using specialists or therapists too. The days of needing to present yourself as some kind of superhuman who is always “killing it” are thankfully mostly behind us. Show care for yourself, and show your care for others by demonstrating that you care for yourself.

I don’t live close, but I run to the office which allows me to get in some daily exercise.

Matt Schulman, CEO & Founder, Pave

It’s a marathon not a sprint. Sleep well and work out. Late nights won’t help.

Job van der Voort, CEO & Co-Founder, Remote

Your sense of wellbeing is also dependent on being able to look at your overall behavior and to feel that you’re acting in accordance with your personal values. This means not only optimizing for your own success and that of your company, but also fulfilling your obligations and duties towards others in terms of care, time and attention. If you find yourself structurally unable to behave ethically, consider what needs to give or change so that you can be at peace with yourself.

If you have a partner and/or children, be mindful of what you might be asking them to sacrifice for the success of your business. Project yourself some decades into the future, and ensure that you won’t regret the choices you’re making now.

Optimize your travel

Business trips are often essential, but can absorb a lot of time and are also physically draining. You want to make them as efficient as possible. Plan them in advance so that you can coordinate scheduling with all parties that you’d like to spend time with (e.g. customers, prospects, partners, team members, candidates, investors, media, etc). Blocking times in advance also allows your EA to plan your route efficiently.

For long haul trips, it’s also time to lose your early-stage attachment to flying coach. The business cost of you feeling more jetlagged is going to outweigh any savings, let alone the physical toll if you’re doing a lot of travel.

Increase your compensation

Assuming that the company is on a strong financial as well as business footing, then you shouldn’t feel awkward about requesting your Board to increase your cash compensation. The business will benefit if you’re able to enjoy a good quality of life. While founder CEO compensation is significantly discounted versus professional CEOs due to the equity disparity, the difference in benchmarks has narrowed somewhat over the last seven years, and are readily available from sources such as Pave. We also believe that founder compensation should take account of personal circumstances—in particular, if you have children or other dependents.

If there’s an appropriate opportunity when you’re fundraising at later stages (from Series C onwards) to sell a small portion of your founder shares in a secondary sale, this could be another way of creating liquidity to improve your quality of life, particularly if you’re looking to buy a home.

Golden age - nautilus

Golden age

The nautilus is a mollusk that lives in the outermost part of its opalescent shell, made up of multiple chambers that spiral out from one another as the creature grows. Each new chamber is formed by dividing the shell at a constant ratio, approximately 1.618. This is known as the golden ratio or phi, and is visible everywhere from petals to pinecones, self-assembling proteins to the ratio of certain planetary orbits.

Phi emerges from the series called the Fibonacci sequence. It was known in Ancient India but later rediscovered and popularized by the Italian Leonardo of Pisa, called Fibonacci, who imagined the growth of a population of rabbits. The sequence starts at 1 and advances by adding the current number to the one preceding it (1, 1, 2, 3, 5, 8, 13, etc). The ratio of each number to the one prior gravitates ever-closer to the golden ratio.

Fibonacci sequences regularly crop up in mathematics and are used whenever computers need to search efficiently, build complex networks of information, or find patterns in large, unstructured pools of data.

Similar patterns of proportionality tend to emerge in high-performing teams—in the ratios between more and less experienced professionals, between visionaries and do-ers, and between leaders and individual contributors. Shaping your company with “golden means” in mind might help you achieve a harmonious, if necessarily temporary, balance amid the chaos.

Stories of Chaos

Dealing with complexity
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Dealing with complexity
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