Learn how Vercel's COO Jeanne DeWitt Grosser builds scalable systems, develops shared mental models, and creates organizations that execute autonomously at s...
Executive Function: Build Systems That Decide Without You
Key Insights
- Operating at Multiple Altitudes: Extraordinary executives balance 30,000-foot strategic vision with ground-level operational reality
- Systems Thinking: The biggest leadership leap is transitioning from individual contributor to building systems where teams execute without constant oversight
- Shared Mental Models: Creating common language, metrics, and frameworks allows people to make decisions aligned with leadership intent
- Pattern Recognition: Staying close to top performers and key initiatives reveals organizational patterns and enables course correction
- Metric Clarity: Unified definitions of revenue and KPIs prevent cross-functional misalignment and enable honest business reviews
The Dual Role of Executive Leadership
When distinguishing extraordinary executives from good ones, the critical difference lies in the ability to operate simultaneously at 30,000 feet and ground level. At Stripe, Jeanne DeWitt Grosser learned that effective leadership requires developing a multi-year point of view on strategic direction while simultaneously building operational capabilities that don't yet exist.
This is especially challenging in today's environment. With artificial intelligence accelerating change, creating reliable two-year plans feels almost unreasonable. Yet executives must maintain this dual focus. There's often a massive gap between the high-level strategic vision and the operational details required to realize it. Not everyone in a company has the experience to translate "this is our northstar" into "here's what needs to happen hour by hour, minute by minute."
As an executive, you're constantly shifting between three modes: building operations yourself, coaching people who have the will but not yet the skill, and delegating freely to those who've done it before. The proportion of time spent in each mode changes as the company scales, but the fundamental challenge remains constant.
At a 500-person company versus a 5,000-person company, the nature of this work shifts in terms of altitude, but not in fundamental principle. As a leader scales their organization through good hiring, they naturally develop more people capable of receiving a northstar, receiving metrics, and executing without requiring deep involvement. However, the most effective executives always identify "three big rocks"—either things they're deeply reviewing or diving into as individual contributors working alongside teams.
Accountability Across Time Horizons
Unlike individual contributors with clear, immediate accountability, executives think across multiple time horizons. An IC's job might be straightforward: "I'm a PM working on product" or "I'm an engineer deploying code" or "I need to hit this number in this segment." Executives operate differently.
Executives are accountable for results within a year but are meant to be long-tenured. Grosser's career exemplifies this: nearly decade-long tenures at Google, Stripe, and now Vercel. This matters because executives must produce results replicably, year after year. This requires a different team structure: most team members execute for in-year results, while a subset of leaders think about next year, and the executive themselves focuses on longer-term horizons—competitive dynamics, market changes, product roadmap evolution relative to customer conversations.
This brings executives to a critical realization: the best executives function as general managers with depth in their functional lane. While owning a specific functional swim lane, they must look broadly across the entire organization. Does finance use the right metrics? Is product's roadmap keeping the company competitive? These cross-functional perspectives enable executives to make trade-offs that might not benefit their own function but position the entire company for long-term success.
The difference between a star VP and a generational COO or CRO often comes down to whether someone can make this transition. Many VPs get stuck because they continue excelling in their specific function without developing the broader systems thinking required at the next level.
Systems Thinking: The Critical Transition
The biggest leadership leap occurs moving from frontline manager to second-line manager (manager of managers). At the frontline, with seven direct reports on average, you can be quite hands-on. At the second line, you can't be in every deal, every product review, or every detailed decision.
Instead, you must design a system. This means understanding:
- Which metrics truly indicate when something's off track
- What are leading indicators versus lagging metrics
- Which forums and review cadences you need to maintain
- Who are the key people through which you maintain pulse
- How to keep awareness without constant involvement
Many leaders get stuck trying to scale via what made them successful as ICs, continuously becoming super-contributors rather than empowering others to be excellent. The transition to systems thinking requires a fundamental mindset shift.
At Stripe, Grosser moved from running sales functions to running global product partnerships—a function where she hadn't sold out of a bag in years. Rather than applying her sales playbook directly, she recognized this required learning the functional context first. She couldn't pattern match from sales experience; she had to understand banking relationships, partnership dynamics, and industry structures. This taught her that functional depth matters less than intellectual curiosity and the ability to contextualize existing frameworks to new situations.
Building Shared Mental Models
One of the most powerful tools executives possess is the ability to build shared mental models throughout their organization. When your team can answer "What would Jean do?" in your absence and arrive at the right answer nine times out of ten, you've succeeded in scaling your decision-making authority.
Several mechanisms facilitate this:
OKRs and Structured Communication: At Vercel, Grosser starts every staff meeting with "Jean's top of mind," explicitly communicating her current mental model. This practice surfaces what she's thinking about and why, allowing the team to understand her decision-making framework.
Shared Language and Frameworks: A segmentation framework lets everyone discuss customers identically. Lead-to-revenue models create shared language about funnel conversion, ACV, timeline, and segment performance. Sales methodologies like MEDIC provide common vocabulary. When finance, product, and sales all speak the same language with common definitions, it prevents the situation where the same data looks green to one function and red to another.
Onboarding New Language: At Vercel, "Know Your Customer" (KYC) is one of the company values. All new hires now receive a KYC onboarding session explaining how to think about customers, how to analyze them, and what the customer segments look like. This creates consistency in how the entire company understands their market.
This approach to shared mental models prevents one of the most common problems in scaling organizations: different functions debating metrics because they define them differently. At Stripe, there was friction between sales (oriented toward bookings), finance (oriented toward GAAP revenue), and engineering (oriented toward usage metrics). This ambiguity created situations where the same business result could appear green or red depending on how you cut the data.
The solution isn't just creating definitions—it's enforcing them systematically. At Vercel, Grosser and the finance team aligned on using GAAP revenue as the company standard. While they still forecast with more granular metrics internally, when the executive team discusses results, they all translate to the same definition. This prevents the political dynamics where functions can claim success or failure based on favorable interpretations.
Patterns, Depth, and Selective Involvement
Effective executives stay close to the most exceptional performers at various layers, which enables pattern recognition. If you're running sales, spend time selling alongside your top sellers. Are their messages evolving? Are they handling objections differently? Are new patterns emerging?
For the initiatives that drive step-function change, executives should be highly involved early, then dial back once the project has "exit velocity." This transition is critical: early on, you're actively participating, commenting on every sentence, attending all initial planning meetings. But the goal is to reach shared mental model clarity such that you can confidently move to bi-weekly or monthly reviews.
This approach requires discernment about which things deserve depth and which deserve delegation. The matrix is simple: identify your three big rocks. These are either areas you're deeply reviewing and staying close to, or areas so complex that you need to get in there actively working alongside the team. Everything else should be delegated with clear metrics and review cadences.
For Grosser at Vercel, a current priority is building enterprise sales capability. Having built her career in PLG (product-led growth) and inside sales, she's now personally making first calls to enterprise buyers. She's recording those calls so the SDR team can hear her approach. By doing the work herself initially, she's establishing the mental model others can follow. She's not delegating this yet because the capability doesn't exist in the organization yet.
Similarly, she launched a GTM engineering team in her first six weeks, pairing sales engineers with data scientists to build a lead-qualification agent. Initial human-in-the-loop versions ran for six weeks before matching human performance. The difference between attempting to delegate something that hasn't been invented yet versus something that's been systematized is stark. You must do it yourself first.
The COO Role: Ownership of Customer Experience Systems
Grosser's role as COO at Vercel differs from traditional COO definitions. Rather than running HR and finance (as many COOs do), her functional responsibility encompasses all "soup to nuts" go-to-market: marketing, sales, sales engineering, customer success, support, and partnerships.
This structure has significant advantages. It creates single ownership of customer experience and revenue. Sales can't blame marketing for demand generation problems; marketing can't blame sales for conversion issues. She owns both. This enables an integrated strategy rather than competing functions operating with overlapping but misaligned goals.
From a product and engineering perspective, this structure clarifies feedback loops. Support has one set of requirements. Sales has another. Marketing is thinking about future product directions. Rather than product and engineering deciding how to prioritize among three competing voices, Grosser reviews all inputs and proposes a unified strategic combination.
However, this breadth comes with trade-offs. While Grosser brings deep sales experience and expertise in go-to-market dynamics, she doesn't have twenty years of marketing experience. She must trust her hiring and leadership abilities to ensure functional excellence in areas where she's less experienced.
The Second-Order Question: What Gets Built?
Beyond executing the functions she owns, Grosser sees her second major responsibility as helping the entire company operate more effectively. This isn't about empire-building her function; it's about asking questions like:
- How can we achieve more unified metrics across the company?
- What segmentation frameworks will help us think about customers consistently?
- Where should we dig deeper, and what insights are we missing?
Her executive team is running a workshop focused entirely on "the how"—how the company operates. This complements the planning session focused on "the what"—revenue targets and how to hit them.
As a fast-growing company like Vercel scales, certain cultural and operational practices that worked at one scale may need refinement at the next. Using tools like CultureAmp for employee engagement surveys (now conducted quarterly instead of annually) provides data on what's working and what isn't. Grosser plans to conduct a "Stop, Start, Continue" discussion with her leadership team—explicit calibration of what they believe is working, what isn't, and what needs to change.
This is important because if the executive team doesn't share agreement on operating mechanisms, they can't maintain cultural cohesion around them. A practice that was critical to product-market fit must be consciously preserved and communicated, not assumed to persist as the organization grows.
Data-Driven Clarity on Product-Market Fit
One of the hardest shared-context problems Grosser faces is distinguishing between product limitations and go-to-market limitations. At Vercel, they have strong product-market fit in the developer community but are now expanding to enterprise.
Are they succeeding in enterprise because they have genuine enterprise product-market fit, or just because they're selling well? This ambiguity creates tension between product/engineering (believing limitations are in go-to-market) and the sales team (believing feature gaps exist). Both are probably partially right.
Rather than debate this politically, Grosser implemented a data-driven approach. They built detailed go-to-market frameworks mapping revenue sources, organic growth, and product-line readiness by segment. This framework asks: "For this customer segment and product, are we completely ready to sell to every company in the world, or are we halfway there?" They rate each combination: "really strong here," "might need one or two things," "need to build this."
This clarity enables joint agreement on roadmap priorities: "This segment and product combination is not our year," or "We're ready to pursue revenue aggressively here." Without this framework, the conversation devolves into functional advocacy rather than data-driven strategy.
Hiring Executives: Contextual Flexibility
When hiring executives to join her team, Grosser screens for several critical attributes. The most important is contextual flexibility—can this person pattern match from their previous experience while understanding what's different about this situation?
Many executives fail because they apply their playbook too rigidly. A classic example: someone highly successful in a consumption-based business assumes payments (another consumption model) requires the same approach. But payments have fundamentally different margin profiles and competitive dynamics. Good executives research the differences and adjust their framework rather than applying it wholesale.
Grosser's interview process assesses this through multiple mechanisms:
First Interview: Understand their background and ask them what they did. Position the role by saying "Here's why I'm hiring for this, and these are the problems you'll need to solve." This direct framing reveals whether they're genuinely motivated to solve those specific problems or simply looking for a title bump.
Second Interview: Provide a prompt about challenges they'd face in the first 90 days and ask them to think through how they'd approach it. Before this interview, Grosser often does a prep call where she gives them additional information and watches which questions they ask. This is "high signal"—the quality of their questions reveals how they break down problems.
Executive Workshop: Have them produce work product addressing three prompts aligned to actual first-90-day challenges. For a CRO search, this might be: develop a go-to-market strategy for a specific customer profile (e.g., Nike's CTO), design an operating model, and propose how to leverage AI and data science in sales.
Cross-Functional Interviews: Have them meet with product, engineering, and other executives. Each stakeholder has veto power, meaning they need to trust this person deeply.
Founder Alignment: Have them spend time with the CEO. Any executive reporting to Grosser must be someone the founder also trusts enough to reach out to directly.
Through this process, Grosser identifies executives who can contextualize, stay intellectually curious, and collaborate effectively. She spots the pattern: failed executives typically didn't get their hands dirty to understand context, tried to apply playbooks too rigidly, didn't adapt culturally, or failed to build networks and cross-functional relationships.
Metrics as Language and Truth
Metrics deserve focused attention because they're surprisingly complex. Two foundational approaches:
Driver Trees: Start with top-line revenue and break it down into the hundred different nodes that drive that outcome. By understanding which specific drivers are moving or stalling, you can identify exactly where to focus energy. For Vercel's B2B segment, Grosser's model showed the business was most sensitive to ACV (average contract value). For the PLG segment, signup conversion rate was the biggest lever. This granular understanding prevents scattershot efforts and enables focused resource allocation.
Unified Definitions: More important than choosing the right metric is ensuring everyone defines metrics the same way. At Stripe, sales thought of revenue as bookings-oriented, finance thought of it as GAAP, and product thought of it as usage-based. The result: the same business could look green or red depending on who you asked.
The solution isn't choosing one definition—it's choosing one, agreeing on it, and reporting consistently. At Vercel, Grosser and the CFO aligned on GAAP revenue as the single company standard. While forecasting and operational reviews use more detailed metrics, executive-level discussions translate to this standard definition.
The Balance Between Support and Accountability
Grosser describes operating in the "upper right quadrant"—simultaneously demanding and supportive. From the demanding perspective: she applies high standards to herself and her leaders, and most people she hires genuinely want great results. The differentiation comes from bringing support.
She's positioned as a best-advice advisor, someone people can bring draft work to, someone who'll help solve problems collaboratively. As long as people communicate, make commitments, and follow through, she works intensively toward solutions. But when people don't communicate problems early, don't escalate issues, or let bad outcomes happen without involvement, they encounter far more friction.
This balance isn't complex once you have the right people and relationships. Grosser does a lot of executive hiring, and she coaches people heavily during the interview process itself. By the time she hires someone, they've already experienced her style: she's demanding but deeply supportive.
She does daily work with her leadership team, emphasizing what she calls "brutal intellectual honesty"—the ability to detach your ego from an idea so that "I'm very smart, I just had a bad idea" becomes the operating norm rather than conflating ideas with self-worth.
Pattern Recognition: Identifying Great Work
Great work should speak for itself, but that's insufficient. Grosser actively highlights work and the people doing it. She spends significant time with people she knows are delivering exceptional results—not because she's checking up, but because understanding what excellence looks like enables pattern recognition.
For most teams, people performing at 3-5x the level of average performers are visually obvious. The challenge in larger organizations is maintaining visibility as layers multiply. Grosser finds that the most exceptional performers often approach her proactively, sharing insights with no expectation of benefit—just genuine intellectual curiosity and helpfulness.
The people who try to benefit-seek (who are "building political capital") tend to be more deliberate about aligning conversations with their schedule. Over time in leadership, these intentions become legible.
One counter-intuitive finding: sometimes people doing exceptional work aren't recognized by layers above because executives sometimes obscure their actual progress. This can be from politicking, but more often it's from brutal intellectual honesty—sharing all the ways something isn't working alongside what you're trying to fix. In contrast, someone less effective might say "we're handling this, we'll solve it" without revealing the underlying challenges. The person being radically honest reveals that things aren't perfect, while the person being strategic reveals only the managed version.
Grosser has learned to embrace radical honesty despite the cost. At one point in her Google career, she realized she was being "out-politicked" by less effective people. But rather than adopt their approach, she eventually left for companies where "intellectual purity" was possible—where first-principles thinking dominates over political maneuvering.
Executive Collaboration: Same Team Mentality
While an executive runs a specific function, they're also part of a broader executive team managing the entire company. This duality requires conscious approach.
Grosser sees her peer set as her primary team, not just her direct reports. In that forum, she should present her functional perspective while promoting better company outcomes. This frequently means operating outside her functional area.
At Stripe, this operated beautifully because the executive team had built exceptional trust and had high-quality leaders who stayed in the room together—sometimes thirty people in leadership workshops and staff meetings. The cost was enormous in time, but the benefit was alignment: everyone heard shared context. A smaller subset then did detailed work together on specific initiatives.
The key distinction: leaders who optimize for company results (even when it costs their own function) versus leaders who optimize for their own interests. The former are rare. The latter are common, especially as companies scale and leaders become territorial about resources and headcount.
Grosser's experience at Stripe involved reorganizing a partnership function where nearly 50% of every direct report's responsibilities shifted. Rather than conventional politicking, the team worked through first-principles discussions about organization design. Several structures (partner-centric, function-centric, geo-centric) were viable. They debated each, then debated why each wouldn't work, then synthesized a superior structure. The key was ensuring everyone knew she'd make the final decision (she had authority) but wanted to ensure all perspectives were heard first.
Workshops, whiteboarding, and extended discussion time were critical. When people can voice concerns and see their concerns addressed in decision-making, they develop less anxiety about outcomes they didn't initially prefer.
Specialized Depth: The Path to COO
Reflecting on her career, Grosser traces her ascent through several deliberate choices:
Following High-Quality Leaders: She purposefully worked for exceptional leaders multiple times. Claire Johnson (worked for her three times), Rich Ralph (worked for him twice, explicitly returning from business school to do so again). These weren't just competent managers—they were people driving exponential growth in their own careers. By adding value to them, she got pulled upward.
Valuing Depth: Throughout her career, Grosser positioned herself as someone strong at certain things, with a clear hypothesis about how she'd learn others. "This job has five major requirements. I'm very strong at three, confident I'll learn the other two." This applied when she moved to APAC at Google (managing both SMB and mid-market when she only knew one), and when she moved to partnerships at Stripe (explicitly telling the CFO she checked half the boxes but believed she'd get there).
Building Organizational Capability: She became known for trying to make organizations better, not just optimizing her own domain. People root for her because she typically helps them be better at their jobs.
In terms of the actual technical skills required: she went to business school specifically because she felt lacking in hard skills (P&L understanding, spreadsheets, financial literacy). Beyond that, most of her development was in leadership—how to operate without authority, how to influence across boundaries, how to communicate effectively, how to lead through change.
The most impactful feedback she received came from John Collison at Stripe: she was demanding and supportive within her own organization but was "dead" to executives in other functions who she deemed ineffective. She wrote them off entirely. While she hasn't fully fixed this tendency, becoming aware of it—and now running multiple functions and developing more empathy for how hard execution is—has made her significantly more open to understanding context she can't immediately see.
Scaling Through Capability Transfer
As individuals ascend to larger leadership roles, they face a critical challenge: they become comfortable with certain skills and continue doing them rather than allowing others to develop. A VP of sales who built their career on PLG might continue managing the PLG segment despite their title expanding to oversee enterprise.
The insight Grosser gained: "You need to kill your job." As you master something, that's the signal to transition ownership. You teach someone below you that skill so they can take over, or you hire someone who brings it, freeing you to learn the next capability.
At Stripe, her career progressed from managing SMB (under 50 employees), to mid-market, to large enterprise. As each capability matured, she progressively focused on the next one. Early in the enterprise shift, she made deals personally to understand enterprise dynamics, but once the enterprise tiger team was established, she brought in an experienced enterprise leader to build that function at scale.
This applies even at massive company scale. The best leaders continue following this pattern: develop a capability, systematize it, hire for it, then move on to what's next.
Time and Attention: Rhythms and Phases
Grosser doesn't allocate her time in fixed percentages. Instead, she cycles between inward-focused and outward-focused periods on a quarterly or multi-quarter basis. Inward-focused periods involve deep dives into organizational design, business metrics, and initiative architecture. Outward-focused periods involve selling, customer conversations, and market engagement.
Both are necessary, but she's found it nearly impossible to do both equally well simultaneously. The switching cost is too high.
Her biggest personal discipline challenge: ensuring time for deep thinking and long-term strategy. This is easily displaced by day-to-day problem sorting, which is tempting because it feels productive. But her highest-impact work comes from having carved out thinking time. Airplane mode is her favorite thinking environment these days.
Quarterly themes also matter. Right now, her theme is building executive sales capability—something Vercel needs as it matures. She's personally making first calls, recording them, and creating playbooks others can follow. In six months, this theme may shift to something else, but the focused investment in building capacity is strategic.
Conclusion
The pathway from talented individual contributor to COO requires conscious development across multiple dimensions: pattern recognition, systems thinking, shared mental models, metrics clarity, and the ability to develop others. Grosser's career demonstrates that exceptional executives aren't born—they're built through following great leaders, developing depth in specific areas, and deliberately choosing organizations where intellectual honesty and company-first optimization are possible.
The highest-impact insight for aspiring executives: most of the magic happens through building systems that make good decisions without you. This requires creating shared language, aligning metrics, developing strong people, and consciously choosing which decisions deserve your personal involvement versus which should be delegated. When your organization can answer "what would the leader do?" and arrive at the right answer in your absence, you've successfully scaled your judgment across the company.
Original source: Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
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