Claire on Scaling People

Claire’s Role in Scaling Stripe

Claire joined Stripe at around 160 employees and helped them scale for several years to over 1000 people. 

1. Norms, Communication, and Culture Setting

Handle Exceptions To Norms Openly, With Clear Justification

• Clearly communicate the expectations and preferences that your company has, but also be transparent when you make exceptions to those norms. 
• ​​If you allow exceptions (e.g., someone works different hours), be clear that this is based on an explicit agreement predicated on their high impact and productivity.
• If someone is not productive, act quickly to remove or correct the issue. Else, you risk undermining the team’s norms.

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Document and Communicate Working Norms as You Scale

• Start documenting your norms early – at the 30-40 employee mark, Claire suggests writing down core working norms, principles, and expectations, ideally as part of your onboarding materials. 
  
  • Don’t wait until you’re 100+ people. Start this process by 30–50 employees so you can onboard new hires consistently and maintain culture as you scale
  • At Stripe, Claire documented the following:
    
    • Vision & Mission: Why do we exist? What’s our purpose?
    • Goals: What are our current objectives?
    • How We Work Together: What are our agreements or norms for working together? Hours? Flexibility? Communication standards? 
• Having these expectations in writing lets you hold people accountable. If someone isn’t aligned with your norms, you can refer back to the written document during performance or exit conversations.
• Claire believes “Policies” are too rigid and legalistic of a word to describe these expectations. Instead, she uses Norms” or “Guidelines” to signal flexibility and shared expectations. 
• Some companies, like Stripe, know they can be flexible. In that case, in your written norms, explicitly note that there can be exceptions—but clarify these should be rare and based on clear, documented conditions (like high-impact, trusted employees).

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2. Organizational Design: Sales and Customer Success

Example: How Claire Thinks about Sales and Customer Success

• As you scale, some functions will naturally require different skill sets. Claire distinguishes these between Hunters, people focused on externally acquiring resources (e.g. Recruiting and Sales), and  Farmers, people skilled at internal nurturing and development (e.g. HR and Customer Success).
• She recommends regularly auditing your organization’s needs:
  
  • Do you need more hunting (external growth and acquisition)?
  • More farming (internal development, retention, and support)?
  • Or a strong balance of both?
• Identify your organization’s biggest gaps and hire or develop talent accordingly, rather than following a rigid org chart or standard reporting structures.
  
  • For example, as you scale, Customer Success (CS) naturally divides into different functions:
    
    • Integration/Deployment: Focused on onboarding and technical setup, requiring specialized skills to get customers up and running.
    • Farming/Expansion: Focused on relationship management, retention, and uncovering opportunities for growth—these roles nurture ongoing customer value.
  • It’s important to explicitly define whether CS is expected to drive revenue. If so, structure compensation and incentives accordingly, but recognize that:
    
    • Most people who are excellent at farming (customer care, retention) are not naturally inclined to hunting (deal closing, upsell).
    • Tying too much of a farmer’s compensation to aggressive sales outcomes can backfire – they may become less effective or disengaged.
  • Over time, organizations like Google, Stripe, and HubSpot found it was more effective to blend pods with complementary skill sets rather than expect individuals to master both roles:
    
    • Pods often pair a senior relationship manager (farmer) who deeply understands the customer with an account executive (hunter) who steps in when there’s a concrete expansion or upsell opportunity.

Your Org Structure Will Depend on Your Business Model and Stage

• For any org decision, consider what specifically that team needs and what goals they’re working towards – this should shape your org design. 
  
  • Some orgs put Customer Success under Sales, others keep them separate, and some larger companies have a Chief Customer Officer overseeing both Sales and Success (plus other customer-facing functions)
    
    • Where Customer Success should sit depends on:
      
      • Your business model
      • How customers are acquired, where revenue comes from, and the relative importance of retention vs. new logo growth
      • The skill sets and backgrounds of current leaders and what gaps exist on your exec team
  • Claire believes that some roles require Hunters while others require Farmers focused on internal nurturing and development. People that excel across both of these skill sets exist, but are rare.

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‍Early-Stage GTM Teams Need Versatility, Not Overspecialization

• Early-stage companies can struggle to cover new sales, renewals, and relationship management without over-specializing into too many roles. This quickly creates complexity and handoff issues. 
• Early on, you don’t want a team with many, highly-specialized roles. Instead, start with team members who have range across multiple functions– for example, sales/CS team members who can both hunt for new business and nurture existing accounts as needed.
• ​​Eventually, most mature orgs have net-new business AEs focused solely on landing new customers, and a separate class of AEs (with different comp structures) attached to pods. Initially, this is too much bifurcation for a small GTM team. 
• To distinguish between the two roles as you scale, communicate goals and expectations clearly and use compensation to clearly signal priorities for each role. 
  
  • If AEs drift into farming/CS territory and miss their growth targets, that’s a leadership issue, and it should impact comp accordingly.
• Every exec will think their team should own Customer Success or expansion. Don’t get bogged down in endless debates and org chart proposals.
  
  • Instead, make a clear “right-for-now” decision on structure, communicate to your exec team that it’s subject to regular review, and keep execs focused on executing on goals instead of territory debates.

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Selling to Enterprises is its Own Skill Set 

• Getting in the door with enterprises requires a very different skill set from managing ongoing enterprise relationships. You’ll often need both, even if they report to the same leader.
  
  • Early on, you might find someone strong at both, but more commonly, these are distinct roles that will need to split as you scale.

3. Hiring a Head of People

Early Heads of People Must Be Hands-On Builders

• Below ~500 employees, most of the work as Head of People involves setting up internal systems, compliance, leveling, benefits, and handling employee terminations. This is usually different from the strategic work experience people leaders crave. 
  
  • Comp strategy is one of the only strategic levers, but early Heads of People rarely get a say here–these are usually owned by the founding team/CEO. 
• Truly experienced heads of people rarely join companies with less than 500–1,000 employees. They prefer to come in once the foundational “building” phase is over.
  
  • This means early-stage companies are left either taking a risk on a rising operator with less experience, or accepting that their Head of People will have to be highly tactical for a while.
    
    • If your Head of People has only worked at a large company, they may struggle with the original building phase. 
  • Many VP of People or Head of People candidates from small companies have inflated titles and haven’t truly led at scale. Director-level or strong senior managers from companies that grew from hundreds to thousands are often better bets.
    
    • Seek out candidates who’ve helped build great People teams at companies at rapidly scaling companies – even if they haven’t held a former leadership title. 
• What to look for in your Head of People:
  
  • Prior exposure to company-building: ideally worked on a great people team under a Head of People you’d want to hire later, and is eager to build, not just maintain.
  • Low drama, good judgment: avoid highly-neurotic candidates or those who seem drawn to “people drama”; you want an honest builder focused on driving business outcomes through people, not internal politics.
  • Willingness to roll up their sleeves: the best early hires are those excited to set up basic systems and infrastructure, even if the work is gritty.
• It will be hard to get a great long-term Head of People until you’re quite big. 
  
  • In the interim, look for a generalist People Lead or Head of HR that can handle building the tools and systems you need early on.  
    
    • Given that the two roles require distinct capability sets, finding someone who can cover both may be difficult. 
    • At ~200 people, Claire hired someone at Stripe to function as an HR lead.

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 Introducing Structure Is Painful, But Waiting Makes It Worse

• Early People work involves setting up job levels, ladders, and compliance. This work is often messy, unrewarding, and under-resourced. 
  
  • When Stripe was at 300 people, Claire introduced job levels and leadership ladders. This was faced with pushback— introducing structure felt demoralizing to early employees. 
    
    • At Stripe, rolling out levels/comp bands at ~300 people was painful, but companies that waited until 800+ described it as a “blood bath.”
• Firing is an unavoidable and often messy part of scaling a company. If no one has experience, the burden usually falls to whoever knows how to do it, making them the unpopular “grim reaper” of the company.
  
  • Even though managers should be able to handle terminations, many often avoid the conversation because they are inexperienced or too scared to do it.  
    
    • Delaying difficult conversations is often why terminations happen in the first place – many times, performance issues fester because managers never knew how to give clear feedback early on.
  • HR’s role is to enable and support managers, providing hand-holding, clear scripts, and guidance through the process.

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Give Standout Internal Talent the Opportunity to Scale, and Watch Closely 

• In an ideal world, most of your senior leaders will come from homegrown talent that’s scaled with the business – they know your product, your customers, and how you operate as a company. 
• In reality, if you’re growing very fast, your talent needs will far outpace your ability to internally promote talent. Even though you’ll have to hire externally, try to decide what proportion of senior leaders you want to hire externally. 
  
  • This is especially important for more senior hires. The more senior your external hire, the more likely they are to not mesh well with your company’s current practices. 
    
    • At Stripe, Claire brought in senior recruiting leaders to nurture a promising hire on the recruiting team into Stripe’s Head of Recruiting.
    • Dell followed a practice called “Scaling to the call”, where high potential internal team members were given the chance to scale up in their role, through either a promotion or a hard assignment, and then observed to see how well they scaled into that function.
      
      • The people that scale well are often eager for feedback and very valuable.

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A Nontraditional Background Can Make A Strong Head of People

• Leaders with nontraditional backgrounds can actually be strong candidates to lead People/HR
  
  • These hires often bring a “product brain” and systems thinking perspective to the function, making them rigorous, and data-oriented. 
  • Example: Facebook once put a product leader on top of People. Stripe’s current Head of People does not have a traditional HR background.
• The main risk with these hires is the lack of legal and compliance expertise. At Stripe, Claire hired an internal employment lawyer to augment her more junior People team, covering regulation and compliance. 
  
  • The legal aspects of the job can be learned or complemented with the right expertise. What you want from a nontraditional hire is a network, a program they can learn through, and people they can upskill from. 

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Great People Leaders Will Anticipate and Call Out Breakpoints

• The best Heads of People that you hire at 500-100 people will push CEOs to confront leadership gaps and think ahead about what will break as the company grows 5x, 10x, 500x its current size.
  
  • These leaders should be truth-tellers – they should challenge founders about which execs won’t scale with the company and force hard conversations before things break.
    
    • Example: “Beth does great work today, but she won’t be able to do this job in two years—what’s your plan?”

4. Compensation

Scaling Compensation is Messy and Difficult

• When Claire first joined Stripe, two things surprised her:
  
  • The lack of management – most people didn’t even know who their manager was 
  • The time and effort that went into managing compensation. 
    
    • Comp is really strategic and incredibly hard to get right. Stripe’s valuation was changing fast – people hired a couple years prior were making far more than others, and there was no real way to equalize compensation across the org. This also meant Stripe’s position in the talent markets was changing.
  • As you scale, you’ll need to rebuild systems for trust, fairness, and communication. At Stripe, this meant Claire spent hours evaluating compensation in Excel, though there’s really no clear way to maintain a perfectly fair system in practice. 

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Balance Comp Transparency with Education and Context

• Full transparency on compensation is rarely practical or helpful – Claire recommends limited transparency instead. 
  
  • Equity is particularly difficult for employees to conceptualize – most aren’t equipped to interpret the full context of comp data, like grant date, share price, current value, vesting, and market changes.
    
    • Avoid telling employees or managers it's "too complicated to understand"; instead, explain that comp is always evolving due to shifting market benchmarks and changing macro conditions.
  • Google implemented a “snapshot” system, where managers would temporarily review spreadsheets with HR during comp/performance planning, provide feedback, and then lose access. 
    
    • To keep total comp private, managers could toggle between either viewing either cash or equity data, but not both. 
• At scale, some companies are required by law to publish salary information. 
  
  • When Stripe reached this point, they published broad salary bands for roles/levels, but kept intentionally wide. 
• Use clear, ongoing education to explain that everyone entered under a different system, emphasizing that bands are based on benchmarks and that volatility in a high-growth startup is unavoidable. Be transparent about the logic and structure, but avoid sharing granular, individualized data that’s likely to create more confusion than clarity.

5. Performance Management and Calibrating Leaders

Move Quickly on Low Performers

• Move quickly on low performers—trust your gut and start asking questions if you suspect someone isn’t working out.
  
  • Low performers at the early stage will hurt the whole company. Holding high standards and being relentless about answers can be very effective for surfacing and addressing underlying problems.

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Every Interaction is an Opportunity to Find Talent

• To be a talent magnet you need to be known for high-quality leadership, ambition, and a positive, well-run company culture.
  
  • Your early talent really matters. Align a strong team around the overall mission of your community – the community you serve needs to notice and respect you. 
    
    • Are you in the right forums? Are you a thought leader in your space?
  • Stripe used hackathon events (like Capture the Flag) to build community, and brand, and find potential hires. 
    
    • Try to do something interesting that’ll get noticed by the community you’re trying to attract. 
  • Every interaction with your team will reflect on your company’s brand – build a reputation as a well-run company. Stripe’s reputation for having no drama went a long way in attracting and retaining talent. 
    
    • Reputation is powerful and sticks with people – this includes your candidate experience for people you don’t end up hiring.

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Invest in Creating Systems You Trust to Scale Decision Making

• To promote ownership while staying involved as a CEO, you have to let people make decisions once you trust them.
  
  • At Stripe, Patrick would go deep into the details if he was momentarily interested in a specific function, but ultimately founders don’t have enough time to go deep into everything. 
• Instead, bring leaders together who first shadow you to learn your taste and judgement, observe how they deliver, and then have them teach others. This is the only way to create a system that you trust and scale without the CEO becoming a major bottleneck.
  
  • For example, Stripe had employees whose judgement and taste were really valuable in API design – Stripe made sure to retain them and give them more responsibility in decisions involving APIs, even if they weren’t the best fit to be managers. 

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Onboarding is Key for Diving Leader Success

• Even when bringing in an experienced leader, founders have to actively manage their onboarding. New execs need to deeply understand your company’s culture, product, and priorities—especially in the first month. 
  
  • Founders tend to go hands off when they hire an experienced leader, even though they still need to be inculcated into your system – they don’t know anything about it. 
    
    • Addressing concerns and misalignment early on gives new leaders the chance to course correct. Waiting to have those conversations almost always results in teams parting ways. 
  • At Stripe, new leaders had an agile daily standup to ensure they were settling into the role well. 
• When onboarding, the goal is to help new leaders thrive in your company’s context, not just succeed in general.

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Align on Benchmarks Early and Often With New Senior Leaders 

• Set clear, measurable goals for leaders, and make sure you’re aligned on the goals they’re setting up for their organization as well. 
  
  • You can delegate setting benchmarks to new leaders: ask them to do their own research and form an opinion on what benchmarks matter, but align with them to make sure what they’re going after is aligned with your vision for the company. 
    
    • The best leaders will actively engage in this process, ask good questions, and form sharp opinions. 
• Look for how much talent each senior leader can bring into your company – if they can’t identify talent gaps, or notice a gap in your team but don’t have any strong candidates they can call, something’s wrong. 

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Meet With Employees Across Company Levels to Collect Feedback

• Meeting with employees at all levels—including skip-levels—is appropriate, not micromanaging.
  
  • Don’t rely only on feedback from “favorites” or friends within the company. Ensure you’re meeting with and hearing from a broad sample, not just those with a direct line to you.
    
    • Regularly meeting with the same skip-level employees can introduce political issues. 
  • Have a systematic approach to collecting feedback – at least once a year, have an employee survey with open-box fields for employees to provide feedback on their managers. 
    
    • Leaders should collect this data and read the comments left by their direct reports
  • Sometimes resistance to new leaders means they're raising the bar, not that they’re failing.
    
    • Take manager scores from employee surveys in context – a low manager score may be because an employee is being managed out – and read the comments. Employees will often softly hint at larger issues worthy of diving deeper into. 
  • Put together small groups of employees and take them out to lunch. Take note of what employee feedback comes up, even softly, and pay attention to the group’s body language in these conversations. 
    
    • If everyone’s aggressively nodding in response to a small, soft piece of criticism – there’s probably a bigger issue there.

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