Karen Peacock on Leading Leaders

1. The CEO’s Job

Set and Relentlessly Communicate the Company’s MSM

• At least once a month, it’s important for CEOs to address the full company on the team’s Mission, Vision, and Strategy
  
  • Repeating your MSM often and with consistent language is critical because employees are heads down in their own work every day, and especially in an environment that’s moving fast, it’s helpful to regularly remind them of their “true north”
  • Brad Smith, who’s one of the CEOs Karen learned the most from would always say “repetition doesn’t ruin the prayer”
• Without constant reminders from the CEO, employees may risk losing sight of the bigger picture and may optimize for tasks that aren’t aligned with the company’s long-term direction 

Framework: Karen’s Six Core Responsibilities for the CEO

• The What: Set mission, vision & strategy informed by customers and market insight to inspire, winning hearts & minds. 
  
  • This should communicate what you’re really trying to do, how you’re going to make it the best job of people’s lives, why you’re in the business, what the vision is and what future state of the world are you trying to create as a company 
  • This should be informed by your customer and market insights. Especially between the Series B and Series D, founders struggle to articulate their MSM from the lens of customer and market insights
• The How: Develop values, key principles, and build an exceptionally strong team. Develop and grow the culture. 
  
  • Have clear key principles that your company operates under and that you share regularly
  • You should also communicate with clarity the bar for what greatness looks like in your team. This will help you assemble a strong team
    
    • As CEO, you should also try and surround yourself with people who are stronger than you in specific domains 
• Execute! Set a high bar, with clear goals (both output and outcome) and hold people accountable to deliver (including yourself).
  
  • Make sure you set clear goals. Karen thinks of goals in terms of output and outcome. The output is important to communicate what specifically you are executing towards accomplishing, and the outcomes communicates what you achieve as a result of the output
    
    • Ex. Your output was to publish an article, and your outcome may be: how many customers you got via the article? What percent of customers who used your product once went back and used it again from the article?
  • Holding yourself and your team accountable also helps you set the culture. There will inevitably be moments where things don’t work out and the way you respond in those situations shows your company’s true values 
• Become a leading voice in the market
  
  • Part of your job as a founder is to set the tone in your space and spend time in the market with customers and whoever the key influencers are of your product or service. 
    
    • Karen emphasizes that you don’t need to be perfect to start, but it’s worth investing in speaking or presentation coaches to continuously improve over time
• Raise capital, allocate capital well, keep shareholders informed and positive.
• Constantly learn, adapt & grow. Keep building and growing aggressively. Set the pace.
  
  • Karen emphasizes that you should be constantly learning, growing, and adapting aggressively. As CEO, you’re setting the tone and pace for the whole team. Ask them questions like:
    
    • What did you accomplish this week?
    • What did you learn last week?
    • How many customers did you speak to? What surprised you in those conversations?
  • You can also ask your leaders to ask this of the people that report into them. These will help set the tone for the pace at which your org should be learning and growing

Q: How much autonomy should leaders have in retaining high performers who are poor cultural fits?

Context: Some individuals deliver strong business value and help their manager hit goals, but demonstrate behaviors we don’t want replicated. How do you navigate situations where removing a cultural misfit could hurt a leader’s ability to hit their numerical targets, especially when compensation is tied to those goals?

Your Culture is What You Permit

• Even in cases where someone is delivering results, if their behavior isn’t one you’d want 20-30% of your org to emulate, you cannot allow it to exist
• Leaders need autonomy, but not at the expense of culture. Karen believes that while this tension is a common challenge for CEOs, you must drive a hard line when behavior undermines the environment you want to build. 
  
  • Karen uses the test: if 20–30% of the team behaved like this in 1–2 years, would I be okay with it? If the answer is no, you can’t permit it.
• Karen compares culture to a bowl of fruit: one moldy raspberry can spread and spoil the rest. If you let toxic behaviors stay because someone is delivering today, those behaviors won’t remain contained to your top performers, they will trickle into average and even underperforming team members

Address Culture Issues Directly and Early

• Karen suggests starting by giving clear, direct feedback to either the leader themselves, or the leader managing this person. In this conversation, share why their behavior is problematic and make sure they understand the pain as well. 
  
  • Karen emphasizes that conversations should always start with the direct manager. It’s their responsibility to hold their team accountable
    
    • If the issue persists, it can escalate one level up, but it doesn’t need to jump multiple layers unless there’s a specific reason (e.g., the IC’s insights are uniquely valuable). As CEO, it’s your job to hold the managers accountable for addressing the issue, not to directly intervene 
  • Karen uses the Situation, Behavior, Impact (SBI) framework to have these conversations. An example of how to use this in conversation with your team members is below:
    
    • Situation: “When you’re in the lunchroom talking with colleagues…”
    • Behavior: “…and you share that you don’t think the company is making the right decision or that leadership is moving fast enough…”
    • Impact: “…it demotivates others and lowers productivity. People look to you as a leader, and that negativity spreads.”
• Karen suggests allowing 1-2 cycles of feedback, but if the person improves briefly and then reverts, you must move quickly to take action. Prolonging your tolerance for behavior that’s negative to your team’s culture signals to the whole company that their behavior is acceptable
• In some cases, removing a toxic but productive employee can actually relieve the broader team more than leaders would expect. Other team members take note when cultural misfits are tolerated and they also take note when leaders take action to protect the company’s culture 

When Performance Conflicts With Culture

• Sometimes letting go of a poor cultural fit will risk a leader missing a number they’re being comped on. This creates a tension where managers may not want to let go of performant hires even if they’re poor cultural fits. 
  
  • Karen suggests approaching these discussions with clarity that your company’s goals are not to be pursued in a vacuum. The “what” (hitting metrics) must always sit within the “how” (integrity, culture, values)
• In cases where you realize you haven’t made cultural expectations explicit enough as CEO, you can offer your leader temporary relief. 
  
  • For example, this may look like adjusting a leader’s comp for the current quarter, acknowledging that the expectations weren’t clearly communicated before. But you reset the standard immediately going forward: cultural misfits cannot stay, even if they’re helping hit the numbers
• While letting go of poor cultural fits who continue to drive performance may be painful in the short term (you may miss a target or have extra work in the intermediate), they reset standards going forward.

2. Building the Right Leadership Team

Q: How do you handle early hires who perform well individually but aren’t scaling into the leadership role?

Context: A first sales hire who is an excellent seller and brings prior leadership experience, but has not met the bar in building and hiring a strong team. How do you have the conversation with this person when you’d like to retain them as an individual contributor, but no longer see them as the right fit to lead the function?

When a Strong Team Member Won’t Make the Right Leader

• Sometimes you’ll have team members with prior leadership experience and there’s an implicit assumption (by them or the team) that they’ll naturally grow into a functional leader. Over time though, you may realize they’re not a right fit to scale the team yet
  
  • Karen stresses the importance of being decisive here: don’t put someone in the leadership role just because of their tenure or past experience. Strong team members don’t always translate into strong leaders. In this conversation, you should also be clear on why you’re making this call
• The conversation you have with the team member should be clear, direct, and framed as a win-win.
  
  • Example framing: “We’ve decided to bring in a deeply experienced sales leader who you and the team can learn from. I see your potential and want to expand your scope whether that’s leading mid-market, helping train new hires, or taking on bigger deals.”
• In the medium term, you may not need two leaders, but you can still create extended responsibilities or projects that allow the other team member to grow.
  
  • Ex: Training sessions for new reps, owning mid-market accounts, or piloting new processes.
• While titles can sometimes help serve as a win-win in these settings, Karen cautions against creating a precedent (e.g., handing out inflated titles like SVP) that could cause problems across the org.
  
  • The goal should be to give them the scope to grow and stay motivated, while filtering out concessions that could backfire with other employees.
• If appropriate, involve them in the hiring process (e.g. as part of the interview panel) so they feel invested, but only if you trust they’ll evaluate objectively and exercise good judgment.
• In these cases, the external hire should be clearly a step above the internal candidate on paper. That way the rationale is obvious, both to the AE and to the team.
• Karen also emphasizes the importance of recognition. Even if you don’t often give praise, this is the time to deliver it. Genuine, well-placed positive feedback will be remembered, reinforces their value, and makes it clear that their contributions matter even without a formal leadership title.

Q: How do you retain and motivate a leader when backfilling their role with a more senior hire?

Context: An excellent IC was promoted into a head of marketing role and has been operating in that seat for ~18 months. Now the company is bringing in a VP of Marketing above them. This means not just a leveling change, but also exiting the leadership group, which can feel like a demotion even though the person remains critical to the org

Retaining Key Talent While Layering Above Them

• Sometimes high-performing ICs are promoted into leadership roles (e.g., Head of Marketing) but over time you realize the org has outgrown them and you need to hire a more experienced leader to come in.
• In these cases the hardest part is not always comp or title changing, it’s the feeling of no longer being in the room where it happens. Losing access to the leadership table can be demotivating, even for employees who remain critical to the company.
• In your conversations, be transparent about why you‘re hiring above them and what it means. Frame it as both necessary for the company and an opportunity for their growth 
  
  • Ex: We’re bringing in a VP of Marketing who can help us get to the next level. You remain critical to this org, and I want to expand your scope in ways that build on your strengths, whether that’s leading mid-market initiatives, piloting new processes, or training new hires. You’ll also remain part of our extended leadership team so you continue to have visibility into where we’re headed.

Q: What’s the right approach to one-on-ones and feedback cadence with senior leaders?

Context: Founders often hear conflicting advice: some say to do regular one-on-ones with every direct report, while others, especially post-“founder mode”, say to cancel them altogether.

It’s Important to Have Regular Touchpoints With Your Direct Reports

• While not all CEOs have or appreciate 1-1s, all CEOs do have regular touchpoints whether async or synchronous with their direct reports
• A wartime CEO is not a noncommunicative CEO. Wartime CEOs touch all their people regularly, and are very clear on where to go and what the pace is. While they may not have a regular pace of meeting with their reports, they’re still making sure they’re getting time to interface with their people regularly, even if it happens organically in the natural pace of work. 
• It’s also important to give people feedback in real-time, because that’s when people learn best. 
  
  • Karen’s SBI framework can be helpful in these conversations
• Karen suggests getting your team together on a regular basis, and emphasizes that even wartime CEOs do this regularly, while it may not be on a set basis (like the first say of every quarter). 

Tactic: How Karen Collects Feedback Within Her Team

• A tactic Karen picked up from Patrick Lencioni’s Five Dysfunctions of a Team is to do speed feedback
• She taken an hour and a half with all her direct reports and each person takes a few minutes to think about one thing each other person on the team does that most helps and most holds back the team
• After everyone has their answers, you start with the leader. The group then goes around and says what the leader did that most helps and holds back the team. This continues with every other member of the group
  
  • Karen finds this exercise more helpful than taking a long time to write performance reviews and get 360 feedback for each person. Through this exercise, in a short span of time the team covers a lot of ground with each person leaving with actionable, relevant feedback
• When Karen first began doing these exercises, she was worried it would be too scary for the group and that certain team members would get really piled on. 
  
  • Instead, she’s found it helpful and affirming every time she’s done it, since team members see that they’re being recognized for and valued for a lot of the things they do, and have an understanding of a few key things they should do differently
• Karen doesn’t do this exercise more than once a quarter. Usually it happens about twice a year, or whenever it feels right for the team. 

Tactic: How Karen Keeps Her Broader Leadership Team Engaged

• To make sure leaders who have to get layered stay engaged and feel involved or groom future leaders, Karen often runs two layers of leadership meetings:
  
  • A weekly exec team with the CEO’s direct reports
  • An extended leadership forum of direct reports and their key direct reports. This group met roughly every six weeks, and had their own email alias/slack groups to make it easy to stay actively engaged.
    
    • This keeps rising leaders engaged in org-level discussions and provides them with visibility, while also giving execs the opportunity to touch a broader set of the org. When key decisions were being made (like senior hires or big changes), the exec team would first share it with the extended leadership team before announcing it to the whole company. The leadership team would also help pressure test these big ideas and changes
    • These forums are used for roadmap reviews, debating strategic shifts, or testing messaging. It provides layered leaders a meaningful way to contribute without being over-extended

Q: How do you support leaders in becoming AI-native?

Context: Company just hired its first sales leader, who is experienced but has never operated inside a truly AI-native company. Some aspects of the role are well-established and should follow tried-and-true best practices. But other aspects are being redefined in real time in AI-native companies.

Developing AI-Native Leaders

• Many functional leaders will come from traditional backgrounds. They bring legacy practices, but may lack instincts for what’s changing in among fast growing AI companies
• Karen suggests a two-pronged approach:
  
  • Build relationships with AI-native companies 1–2 years further along. Pair your leaders with their counterparts to learn how functions like sales, finance, or marketing are evolving in this new environment. As founder, also connect directly with those CEOs to spot differences yourself
  • Work with your leaders to bucket challenges into:
    
    • What’s consistent and proven (playbooks to follow)
    • What’s clearly different in AI-native companies (where old playbooks break)
    • What’s uncertain and requires experimentation (where your company can lead the market)
• Frame your conversation with the leader as: “You bring a lot of experience we need, and I also want to give you space to help define the new playbook for AI-native companies. Some things will stay the same, but others are changing quickly, and nobody has all the answers. My goal is to make this a career-defining role for you to become one of the first functional leaders who’s truly AI-native”
  
  • This approach positions your leaders not just as operators, but as pioneers, giving them ownership over shaping how their function works in AI-native companies

Q: How do you onboard leaders to get up to speed quickly?

Context: Early go-to-market and functional leaders often fail not because they lack experience, but because they don’t fully internalize the product, customer, or motion they’re stepping into. Effective onboarding involves finding ways to compress how quickly new leaders get immersed in the customer and product. 

Onboarding Leaders

• Karen emphasized that effective onboarding is about immersing new leaders across the company so they can build credibility quickly and gain context
  
  • Have new sales and marketing leaders sit in on sales calls across the funnel, shadow customer support, and spend time with product teams.
  • At Intercom, Karen even worked as a BDR and support rep to internalize how customers felt
• Go-to-market leaders often fail because they never deeply learn the product. Karen has them demo the product back to their peers. 
  
  • It’s uncomfortable at first, but it forces them to develop fluency and builds respect with product and engineering
• Have new leaders spend time understanding customers, the product, the market, and rival products so they can position effectively and spot differences that matter.
• Set clear upstream outputs and outcomes so you’re not blind for six months:
  
  • Outputs: concrete work they and their teams will do (e.g., content produced, campaigns launched).
  • Outcomes: early funnel signals that show whether the work is landing (e.g., engagement, lead volume and quality, conversion at each stage).
  • The sooner you put these metrics in, the sooner you can course correct, coach effectively, and avoid the failure mode where issues only surface when revenue lags

Q: How should we define leadership expectations in a culture where long hours are the norm?

Context: Sometimes senior leaders are used to working hours that differ from the pace and intensity of many scale up companies. In these cases, leaders who work different hours may come across as not being “in the trenches” with their teams.

Cultural Expectations for Senior Hires

• Be explicit about hours and expectations upfront. These will vary by function: having an engineering leader who works hard is non-negotiable. You need a leader who is visibly in the trenches, working as hard as the team. If you compromise here, you will dilute the org.
• However, there’s more flexibility for post-sales / account management. Leaders can manage family commitments or carve out a couple hours offline, as long as they own the outcome and role-model accountability.
  
  • In these cases, some offline windows are fine (e.g. offline 6–8pm then back online). Others (e.g. offline 3–8pm) likely won’t work for your org. The key is for the leader to clearly own their outcome. 
• Karen strongly suggests not to settle and to wait for the right hire. If it means extending the search, or switching search firms to find your “unicorn hire” do it. 
  
  • A VP of Engineering who won’t grind will fail to earn trust and will lose the team.
• Use the “reverse pitch.” Lay out the reasons not to join (long hours, intensity, cultural norms) so candidates self-select in. Better to filter early than have a failed hire three weeks in. The reverse pitch often flips candidates into selling themselves on why they do want the role.
  
  • At Faire, Max Rhodes would explicitly communicate to all senior hires that the whole company was expected to be online from 8-6
  • Karen uses a similar approach with candidates: She leads by expressing that “This job isn’t for everyone.” She sets expectations that the job will be intense, involve constant learning, and feel uncomfortable at times. 
• Regional cultures also shape expectations. In some countries, norms around vacation or hours differ, and compensation typically adjusts accordingly. Karen’s approach is to align local pay with local expectations. 
  
  • Teams in markets with six weeks of vacation get that, but it doesn’t automatically apply company-wide.

Covering for a Critical Leader on Leave

• Senior leaders generally don’t take very generous leaves. In cases where they do, however, Karen suggests by first breaking the job down into sub jobs. For each sub-job, explicitly decide what stays on their place part-time vs. what must be delegated. 
  
  • This should be written down. Else the ambiguity will confuse your team and slow the company down
• Assign clear interim owners. Name a person for each responsibility with the goal that no one on the team should wonder who’s in charge of X task during the leave. 
• You can scope the sub jobs your leader can still own against their available time. For example, if your leader is working 3 days a week and there are 5 sub jobs, you can roughly estimate that he’ll cover three of the sub jobs
  
  • How you scope these responsibilities depends on how much ownership your leader has over their outcomes, the nuances of each sub job, and the nature of how involved they remain during their time off. Some leaders will over-deliver even while “part-time.” That’s great, but your system should not depend on it. Build a plan that works even if he’s truly offline the other days.
• These moments are also helpful to test whether your senior leader was previously spending too much time in the weeds. If some of these jobs can be executed at 60% capacity without any gaps by other team members, your leader may not need to retake every sub job. This should free up their time for higher-leverage tasks
• You should communicate explicitly with your team that the company cannot afford even a 1% dip in pace while the leader is away. You should write this expectation down and communicate it, with the message being that the pace will stay the same or even be accelerated while they’re away.
• As a CEO, this is also a chance for you to see:
  
  • Who on your team naturally steps up to take on bigger responsibilities?
  • Which processes are running well without your senior leader in the weeds?
  • Where do gaps show themselves without them? These are fragile gaps in your org

Q: How do you reset expectations with internally promoted leaders?

Context: Company promoted several staff engineers into people lead roles last year, but didn’t set a strong calibration at the start. Some projects ended up over-scoped or missing details, and one lead in particular hasn’t shown much proactivity without direct instruction. That dynamic is now ingrained, and it feels awkward to suddenly raise the bar.

Resetting Expectations with Internal Promotions 

• You may sometimes fall into the trap of having promoted managers that you realize in retrospect may have been promoted prematurely. You’ll want to help them grow into better leaders but it’s hard to change you existing dynamic and set new expectations for how involved you’re going to be with them 
• Karen suggests making a change as soon as you realize something hasn’t been going the way you expected. 
• To make a change, mark a clear break. Karen suggests starting by writing down the current state of the world, and how you want things to be (your target state)
  
  • Use this as the backbone of your reset conversation. Frame it as the company entering its next chapter and hitting a higher bar.
  • In this conversation, you can make it clear that the org will be operating in a different way and that you want to take a week with each team to decide what that will look ike
    
    • You can also leverage branding (e.g. Engineering 2.0) to drive the point home that the org is going through a step-function change. 
    • You can tie this conversation to the org’s mission and values (e.g. building a generational company requires proactive leadership, crisp scoping, and higher accountability).
• Once expectations are reset, give your leaders direct feedback against the new bar and be honest with yourself on whether they’re meeting it. 
  
  • Within engineering, Karen likes to have a leadership track and an engineer track to delineate between growing people leaders and talented technical team members going on to be principal engineers/ICs who can drive as much impact through their engineering work. 
• Move quickly once you realize expectations need to shift, and avoid purely reaction-based feedback (after a project is already in motion). Instead, set ways of working upfront:
  
  • Define project goals
  • Agree on success criteria
  • Establish best practices for how the leader should execute before work begins

3. Making the Right Hires for Growth

Q: Should you hire a GTM leader who’s a fit today (a leader who can execute against what’s already working) or a fit for what you don’t yet know (a leader who can help you discover and shape new motions)?

Context: Company is developer-focused, with both a self-serve PLG motion and an emerging enterprise motion. Different GTM leader profiles may be better suited to one versus the other

Choosing Your First GTM Leader

• Many companies often start off with a self-serve PLG motion and build out a larger enterprise motion later on. 
  
  • In these cases, it can be confusing to decide whether to find a leader that can help you figure out and lean into what’s working well so far, versus finding one that can help you figure out what you don’t know already 

Tactic: Filters for Choosing Your First GTM Leader

• Karen’s first filter is to optimize a hire for the next two years, not forever. The average tenure for a first sales leader is about two years, so hire someone who will be exceptional at the 12-18 month mark, not someone who may only be valuable in year three.
  
  • Ideally your hire will get up to speed in 3 months and be the right fit for where your product and sales motion will be in a few months and will peak within that first 12-18 month window. It’s okay if by month 24 they’re no longer the perfect fit as your product and sales priorities change, statistically speaking you’ll likely have to find another person anyways. 
• Karen’s second filter is to hire someone who has sold specifically to your target customer, at the price point you’re at today or plan to reach in 6–12 months. 
  
  • For example, in the case of a devtools company, she recommends finding a hire who has sold to developers before, since that audience is very different from typical business functions within an org. 
  • You also want to anchor your leader at today’s ACV. If your self-serve tops out near $30k and your light-touch motion lands $100k deals, pick a leader who has repeatedly closed $80–100k contracts with developers. Avoid million-dollar “whale hunters”: they may chase low-probability deals instead of building volume in your core band
• Karen also stresses the importance of aligning scope and incentives with the band you’re targeting and being opinionated about where most of your revenue will be coming from over the next two years. 
  
  • If your focus is on scaling the $80–100k engine, the hire should be measured against metrics that reflect that motion, like qualified pipeline from PLG signals, conversion rates, cycle time, and overall repeatability. 
  • Compensation should be designed to reward volume and velocity in this ACV range, not one-off whale deals that distract from the core motion

Scaling Upmarket Is a Strategy Call

• To determine whether your leader should spend time on whales or not, Karen suggests deciding whether the company has explicitly decided to move upmarket in the next 12-24 months as part of a key strategy change. 
• This is because selling large, $1M+ deals is different in a few ways:
  
  • They come with many product and roadmap changes and often have many bespoke asks
    
    • For example, Intercom entered into a sales cycle with IBM for what was going to be a contract 10x larger than what Intercom’s largest customer was paying them. While the whole team was initially fired up and had decided to scale engineering to meet the sale, IBM came back with 150 bespoke asks and the company decided to sunset the sale.
  • These sales motions have different support and SLA expectations
• Ultimately, Intercom had over 400 customers paying them 200k+ and only a handful paying 1M+. When Karen joined initially, Intercom’s ACV was 10k, so while it’s possible to scale, it’s worth growing one step at a time
• Many B2B companies will either get an SMB or enterprise leader and ask them to cover mid-market as well. Instead, try and be opinionated and prescriptive about where your company’s needs will be and hire accordingly

4. Managing Conflicting Feedback

Q: How should founders weigh their own instincts against input from trusted advisors when making senior leadership hires?

Context: Founders often have strong conviction about the product and customer, but less direct experience hiring senior functional leaders. As a result, board members and advisors can have an outsized influence in these decisions. It’s sometimes challenging knowing when to defer to outside expertise versus when to trust your own instincts. 

Framework: How Karen Navigates Conflicting Advice

• In cases where you receive conflicting advice, Karen suggests weighing No’s more heavily than the Yes’s. 
  
  • For example, if a board member says yes to a hire, you should take it as a positive data point, whereas if they strongly disagree with a hire, it’s worth giving their opinion more weight. You can think of a yes as being a necessary-but-not-sufficient data point towards your decision.
• To come to her own conclusions, Karen likes putting candidates in the job. To make this as real as possible, ask the candidate to do whatever you’d want them to do in their first few weeks in an environment that closely resembles the real day-to-day of working at your company. This often takes shape in the form of a mini project during the interview process, and sometimes Karen will do a couple rounds of this exercise to ultimately make her decision. 
  
  • For a Head of Sales hire, this may look like having them spend time with the product and then having them pitch you on it, deliver feedback based on their understanding of what customers may want, or objectively handle what potential customers may say. 
  • When doing this, make sure to be respectful of the leader’s time. They are likely still managing another full time job while going through your process. 
• Karen believes you find the best fit when you put people in the actual job. The reason for this is that oftentimes founders feel unsure about evaluating people but are far more certain of how to evaluate work. Having candidates go through this exercise allows you to move your evaluation of the candidate into your evaluation of the work. 
  
  • Oftentimes this allows founders to play more into their strengths when hiring. When Karen does this exercise, she usually comes to a far more confident answer within the first few minutes of discussing with the candidate.
• Karen emphasizes that ultimately founders have the intuition to know what’s best for their company. When truly in doubt, it’s okay to trust your judgement.