Tag: employee retention at startups

Inside the Most Politically Dangerous C‑Suite Role: Hard Truths on Culture, Layoffs, and Leadership

I’ve long believed the people function is a strategic engine, not a support lane. That conviction was only reinforced in a recent deep dive with Katie Burke, now COO at Harvey after joining as Chief People Officer. Before Harvey, she spent 11 years in HR leadership at HubSpot, helping build one of tech’s most distinctive cultures. In this piece, I unpack what resonated most for me as a product leader: a marketing-minded approach to HR, deliberate hiring from hospitality, and the non-negotiable case for culture as a core business strategy.

The first principle is simple and often overlooked: HR leaders should think like marketers. Employer brand is a product; your candidate and employee journeys are funnels; and your programs deserve the same rigor we bring to product—segmentation, positioning, channels, and continuous A/B testing. When we treat onboarding, performance, and manager enablement like iterative product launches—complete with activation metrics, retention curves, and NPS—we stop guessing and start compounding results.

One line has become a north star for how I approach executive leadership: “Don’t ask for a seat at the table. Build the table.” In practice, that means codifying the operating system—decision rights, principles, cadences, and accountability—so the organization isn’t improvising strategy in every meeting. Product, People, and Finance should co-own this OS; that’s how you scale clarity faster than headcount.

Transparency is the tax we pay for alignment, and it compounds trust. After an IPO, the impulse can be to close ranks. The better move is radical transparency with context: what changed, why it matters, and how decisions get made now. On my teams, that looks like publishing decision records, sharing tradeoffs explicitly, and using written docs to reduce rumor velocity—core muscles in stakeholder management as complexity grows.

I also loved the counterintuitive hiring bet: prioritize hospitality backgrounds alongside traditional corporate pedigrees. People who’ve thrived in service environments bring customer empathy, operational resilience, and a bias for proactive care—traits that elevate everything from onboarding to incident response. In product terms, they’re culturally accretive hires with high signal on service quality and consistency.

The trickiest part of the Chief People Officer role isn’t process—it’s politics. You are the executive team’s own HR business partner, which requires coaching, candor, and conflict mediation at the highest stakes. The goal is to “Be the Michael Jordan of your exec team”—the teammate who elevates standards, makes others better, and chooses the hard right over the easy familiar.

Layoffs create a culture debt that accrues interest. Expect a “2.5-year cultural hangover after a layoff”—in many companies, an inevitable two-year layoff hangover—unless you actively repay it. That repayment plan includes narrating the why with specificity, rebuilding trust through manager enablement, and re-anchoring on performance and values. Measure leading indicators (manager effectiveness, time-to-decision, psychological safety) alongside lagging ones (regretted attrition) to track the true recovery arc.

People leaders also need to create “graceful exits.” Doing this well preserves dignity for the person, protects the team’s morale, and safeguards the company’s brand. The bar is straightforward: clear rationale, fair process, useful feedback, generous support, and alumni pathways. A graceful exit signals that even when business realities bite, respect is non-negotiable.

Expectation-setting matters. Two truths cut through the noise: “The workplace shouldn’t be Disneyland” and “Our job is not to make you happy every day.” The promise is not perpetual happiness; it’s meaningful work, fair standards, growth opportunities, and leaders who tell the truth. When we set that contract clearly, engagement becomes an outcome of purpose and progress—not perks.

On feedback, I use the protein vs. sugar rule for employee feedback. Sugar feedback is pleasant and perishable; protein feedback is specific, sometimes uncomfortable, and growth-driving. Great cultures build a taste for protein—clear role expectations, crisp examples, and written follow-ups. Mechanically, that looks like structured 1:1s, decision retros, skip-levels, and manager training that demystifies “what good looks like.”

Being a Chief People Officer isn’t for the faint of heart. The role must be demanding by design—on executive hiring quality, performance management courage, and values enforcement. Moments like “Berry-Gate” are reminders that small symbolic issues can balloon when feedback loops are unclear. Close the loop fast, publish the rationale, and ensure there’s a predictable path for concerns to be heard and resolved.

When hiring, beware patterns that predict friction. That’s why “frequent flyers” are a new-hire red flag. Movement can signal adaptability—but weather-vein pivots and blame-shifting often repeat. Probe for ownership, learning moments, and sustained impact; you want people who compound value, not just sample it.

Clarity on scope prevents leadership whiplash. Which company decisions fall to the Chief People Officer? Think leveling frameworks, compensation philosophy and bands, performance calibration, manager standards, ER policies, and org design guardrails—always in lockstep with Finance and the CEO. Escalate when there are values collisions or systemic risks; otherwise, push decisions to the right altitude and owner.

Scaling exposes the same few failure modes on repeat: fuzzy decision rights, a thin manager bench, brittle processes that don’t flex, and inconsistent leveling that erodes trust. The antidote is an operating model that pairs clear principles with lightweight mechanisms—documented roles, regular calibration, and reviews that audit for both outcomes and operating behaviors.

Comparing a scaled SaaS like HubSpot with an AI-native company like Harvey surfaces important differences. The former optimizes for durable systems, predictable cadences, and governance; the latter optimizes for rapid learning loops, emergent org design, and a higher tolerance for ambiguity. The art is porting the right controls at the right time without crushing velocity.

AI is already changing the people function. GenAI can draft job descriptions, summarize performance notes, classify themes from engagement surveys, and power AI workflows that resolve common HR tickets. The human-in-the-loop remains essential for judgment, context, and ethics—especially around data governance and privacy-by-design. A pragmatic AI Strategy here frees HRBPs for higher-order coaching and organizational development work.

One practice I recommend widely: share your own performance reviews. Modeling openness normalizes growth and turns feedback into a shared craft, not a secret ritual. It also builds trust when you later ask the organization to lean into sharper, protein-rich feedback.

Finally, disagreements with the CEO are inevitable—and healthy. Handle them with pre-briefs, crisp written proposals, explicit tradeoffs, and a shared decision record. Argue like scientists, not politicians; once a call is made, disagree and commit. That combination of candor and alignment is what keeps executive teams high-trust and high-velocity.

The people leader’s chair may be the most politically dangerous role in the C-suite—but it’s also one of the most leveraged. Build the table, tell the truth, design for standards and dignity, and treat culture like the product that powers everything else.

April 10, 2026
Inside Zipline’s Wild Pivot: My Take on Hiring Heat-Seekers and Scaling to 5,000 Hospitals

I’m consistently drawn to stories where product strategy and operational grit collide to change real lives. Zipline, the world’s largest commercial autonomous delivery system, is one of those rare cases. Serving 5,000 hospitals across multiple countries and saving an estimated 17,000 lives per year, it embodies the kind of mission-driven execution I try to model in product management. The arc—from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown—offers some of the clearest lessons I’ve seen on hiring, leadership, and product-market fit under extreme constraints.

One principle that immediately resonated with me: why Zipline doesn’t hire for experience. The idea behind “Why Zipline hires teenagers over PhDs” isn’t a dismissal of expertise; it’s a commitment to learning velocity, ownership, and unteachable hunger. The best startup employees, as described here, are “heat-seeking missiles for pain”—people who chase the hardest problems, not the shiniest projects. In my org, I look for the same signal: candidates who can move from ambiguity to action, who find the bottleneck without being asked, and who care more about outcomes than optics.

I also appreciated the unapologetic stance that “blind references are a non-negotiable.” In high-stakes builds—especially in regulated or safety-critical categories—the cost of a mis-hire compounds. I routinely validate for two traits during references: intellectual humility and accountability. “Can candidates admit when they screwed up?” is a powerful filter. If someone can’t name a hard mistake and how they specifically changed as a result, they’re unlikely to scale with the organization.

Equally important is clarity about who not to hire. The employees Zipline doesn’t want are those who optimize for status, process theater, or low-friction work. In practice, that means pressure-testing for problem-finding, not just problem-solving. I often design interviews around messy, cross-functional constraints (regulatory, operational, and financial) to see who can integrate tradeoffs, not just ideate features. That’s how we build empowered product teams that ship consequential outcomes, not outputs.

There’s a reference to “Zipline’s secret leadership playbook,” and while the specifics remain private, the spirit is unmistakable: first principles decision making, ruthless focus, and a culture that rewards radical responsibility. Translating that to my product organization, I emphasize five behaviors: orient to the mission under uncertainty, run fast but close the loop with data, communicate constraints early and often, own the long tail of consequences (especially in safety and reliability), and scale judgment by teaching the why, not just the what. That blend of clarity and autonomy is the backbone of product management leadership at any growth stage.

On the other side of the culture coin is “Why you should always fire quickly” and “The brutal firing advice that shaped Keller’s leadership.” I’ve learned (sometimes the hard way) that slow decisions erode trust and team velocity. Moving quickly doesn’t mean being harsh; it means being fair, explicit, and humane—tight feedback loops, role clarity, and decisive action when the gap persists. If your bar is clear and your coaching is consistent, acting fast protects both the mission and the team’s energy.

Strategically, the origin story reads like a masterclass in choosing the right problem. The team moved “from toy robots to drone delivery: Zipline’s pivot,” then partnered deeply with Rwanda, where “How Rwanda’s health minister changed everything” is a pivotal moment. It wasn’t a linear climb—”How Zipline almost died – twice” and “Why Zipline’s launch was a ‘complete disaster’” underline a tough truth: breakthrough products rarely arrive fully formed. What matters is the operating cadence that turns early chaos into repeatable reliability—especially when the stakes are measured in minutes and lives.

Scaling from 1 hospital to 5000 required more than product brilliance; it demanded systems thinking across logistics, compliance, safety, and community trust. That’s stakeholder management at its highest level. The product lessons are durable: anchor on outcomes, not artifacts; build reliability as a feature; and practice founder-led GTM where your credibility is on the line with customers and regulators. This is where first principles decision making beats benchmarking—particularly in novel categories where there are no playbooks to copy.

There’s also a hard-nosed operational takeaway in “The 10x hardware cost rule every founder should know.” My read: assume total cost of ownership will balloon once you account for manufacturing variability, support, redundancy, maintenance, and compliance. In product strategy, I treat those multipliers as design inputs, not afterthoughts. If the unit economics can’t survive these realities, the idea isn’t ready—no matter how elegant the prototype looks in a lab.

Across all of this, a few product management patterns stand out for me: build teams around outcomes vs output OKRs; hire for slope, not just intercept; make continuous discovery routine with real users (in this case, clinicians and health systems); and treat operational excellence as a product surface. When a mission is this consequential, culture becomes a safety system—and every leadership decision compounds into either speed with quality or speed with regret.

For leaders building in complex domains, this journey is a blueprint: pick problems that matter, hire “heat-seeking missiles for pain,” keep blind references non-negotiable, lead with first principles, and scale with responsibility. Do that well and even a “complete disaster” launch can become the inflection point of a category-defining company that flies 135 million autonomous miles and saves 17,000 lives per year.

March 12, 2026
Stop Groupthink in Hiring: Proven Product-Led Tactics to Make Faster, Fairer Decisions

Is hiring broken—or just badly designed? I’ve been sitting with that question after a recent conversation that crystallized what I see across product organizations: AI-fueled application overload, sprawling interview loops, and fuzzy criteria that invite groupthink at exactly the wrong moments. If you’ve ever watched a promising candidate stall out late in the process, you’re not alone. Listen to this episode on: Spotify | Apple Podcasts.

Here’s the reality I’m observing in the market: Layoffs and hiring freezes have flooded the funnel, while AI tools make it trivial to submit hundreds of applications. Companies are overwhelmed, so they respond by adding more interviews and more stakeholders, hoping more touchpoints equal better signal. In practice, that complexity often dilutes accountability and increases noise—especially for product management leadership roles where clarity, not consensus theater, determines success.

I’ve seen too many offers derailed by “one last step.” A candidate clears every structured interview, then a casual lunch or unframed panel suddenly becomes the deciding factor. The team isn’t briefed on what to evaluate, one lukewarm comment lands, and group dynamics cascade into a no-hire. That’s not rigor—it’s randomness masked as prudence.

Groupthink ≠ good hiring decisions. When everyone has veto power, risk-averse no-decisions become the default. Focus-group-style interviews create bias, not signal, and “culture fit” often becomes a proxy for stereotyping or personal preference. As product leaders, we’d never ship a feature based on vibes; we shouldn’t make high-stakes hiring calls that way either.

There’s a better way—and it mirrors how we run great product discovery. Define who you’re hiring before writing the job description. Set clear success metrics for the role. Assign each interviewer specific criteria to evaluate. Treat hiring like product discovery: intentional, structured, and evidence-based. In my teams, that looks like tight scorecards, interviewer calibration, and a decision owner who synthesizes evidence—not a popularity contest where the loudest voice wins.

Chemistry checks still matter, but only when we define what collaboration actually means for the role. Introversion, debate style, or lunch-table small talk are not performance indicators. I look for behaviors we value in empowered product teams—clarity of thinking, healthy dissent, co-creation under constraints—often via a real working session with the future product trio. Diverse teams outperform homogenous ones, even if not everyone “vibes,” so I optimize for complementary strengths over sameness.

If you’re a candidate, remember: When a process feels broken, it’s often not about you. Ask how you’re being evaluated to gauge process maturity; a thoughtful team will happily walk you through their rubric and what great looks like. For structure and support, I’ve seen “Who: The A Method for Hiring” help leaders clarify requirements; “Never Search Alone” and joining a Job Search Council (JSC) can give you peer accountability and sharper narratives. For current openings, I regularly point PMs to Scott Baldwin’s PM job postings on LinkedIn.

My challenge to fellow product leaders: Audit your hiring process the way you’d audit your roadmap. Where are decisions getting stuck? Where are you over-indexing on consensus and under-indexing on evidence? Tighten the criteria, streamline stakeholders, and instrument the funnel so you can learn and improve. The payoff is faster, fairer, more confident decisions—and teams that reflect the rigor we expect in product strategy and stakeholder management.

What’s one change you can make this week—reworking the scorecard, calibrating interviewers, or replacing an unstructured lunch with a real collaboration exercise? Small improvements compound. Let’s build hiring systems that are worthy of the talent we’re trying to attract.

Inspired by this post on Product Talk.

February 3, 2026
4 Proven Ways to Keep Employees Informed and Engaged—from Onboarding to Lasting Adoption

Keeping employees informed and engaged isn’t just a communications challenge—it’s a product challenge. When we treat internal tools like products with clear activation moments, measurable outcomes, and continuous discovery, adoption moves from hope to habit. Over the years, I’ve seen small changes in how we onboard, communicate, and measure compound into dramatically higher engagement, better compliance, and faster time-to-value.

“How to improve onboarding, compliance, and internal communications within your employee tools.” That question guides my approach end to end—from the moment someone logs in for the first time to the day they become an expert, championing best practices across their team.

First, I personalize onboarding to accelerate user activation. I map the critical first actions and design a lightweight sequence of product tours and in-app guides that surfaces only what matters right now. Progressive disclosure, clear UX writing, and thoughtful tooltip design reduce cognitive load. I measure time-to-first-value, A/B test checklist microcopy to remove friction, and use Intercom or Pendo to deliver contextual walkthroughs by role, location, and permission level. Amplitude analytics helps me validate that the guided path leads to the intended activation event and sustained usage.

Second, I make compliance effortless and measurable. Instead of long trainings, I embed micro-learnings and policy nudges directly in the flow of work, with just-in-time prompts and short, scenario-based confirmations. I segment by role to avoid alert fatigue and localize where regulations require nuance. Completion rates, quiz accuracy, and time-to-complete are tracked alongside qualitative feedback. When compliance messaging underperforms, I run A/B testing on tone, timing, and format, then iterate until adherence is both higher and faster.

Third, I orchestrate internal communications as lifecycle messaging—not announcements. Employees get targeted release notes, role-specific tips, and in-app reminders aligned to their stage: new, adopting, proficient, or champion. I avoid channel sprawl by making the primary source of truth available in the product, then reinforcing it via email or chat only when necessary. CRM integration and audience rules ensure relevance, while a champions network and office hours create human touchpoints that deepen trust and accelerate adoption.

Fourth, I close the loop with analytics and continuous discovery. I instrument key events and run retention analysis to understand which behaviors predict long-term engagement. I look at cohorts before and after a new guide or product tour, and I compare lift in user activation and feature adoption over 14-, 28-, and 90-day windows. Amplitude analytics provides the behavioral picture; surveys, interviews, and passive feedback widgets explain the why. Together, these inputs power a product-led growth approach for internal tools—observable, repeatable, and improvable.

When teams ask where to start, I pilot one persona, one workflow, and one high-value outcome. I define the activation event, instrument it, launch a single targeted in-app guide through Pendo or Intercom, and A/B test the onboarding microcopy. Two weeks later, I review retention cohorts and completion data, talk to users, and either scale the pattern or iterate. That cadence builds credibility quickly because it ties every communication to a measurable result.

The payoff is tangible: faster onboarding, higher compliance, clearer internal communications, and employees who feel supported rather than overwhelmed. With disciplined messaging, smart instrumentation, and ongoing discovery, we can turn internal tools into catalysts for performance—and transform engagement from a campaign into a culture.

Inspired by this post on Pendo – Best Practices.

January 6, 2026
Organizational Development Demystified: The Engine Behind Smarter Teams, Culture, and Growth

When people ask me how product organizations actually scale what works, I point them to a simple truth: organizational development is the operating system that makes strategy executable, teams empowered, and outcomes repeatable.

It turns out that organizational development isn’t just HR lingo. It’s the engine behind smarter teams, better culture, and long-term growth.

In practice, I think of organizational development as the discipline that aligns structure, incentives, rituals, and learning loops so empowered product teams can do their best work. It connects product management leadership with execution through clear decision rights, transparent roadmapping, and ways of working that reduce friction across product, design, and engineering.

On the ground, this looks like moving from activity measures to outcomes vs output OKRs, forming durable product trios to own customer problems end to end, and tightening stakeholder management so priorities don’t whipsaw week to week. It also means investing in onboarding that accelerates time-to-impact, creating feedback rituals that surface risks early, and using retention analysis to make smarter bets about where to double down.

The payoff is tangible: faster decision-making, fewer handoffs, and clearer accountability. Teams ship with confidence, leaders get leading indicators instead of lagging surprises, and employee retention at startups improves because people see how their work connects to a meaningful value proposition and product-led growth.

In my own practice, shifting to outcomes-first planning, establishing product trios, and clarifying interfaces across functions reduced decision latency, improved deployment frequency, and made ownership unmistakable. The organization became more resilient because the culture, processes, and metrics reinforced one another instead of competing for attention.

If you’re starting from scratch, begin by aligning on a small set of outcomes that matter, then redesign ceremonies and artifacts to serve those outcomes. Next, empower teams with clear autonomy and constraints—enough freedom to discover, enough guardrails to focus. Finally, make learning visible: use lightweight postmortems, discovery reviews, and customer signal dashboards so your operating system continuously improves.

Organizational development isn’t a one-time reorg; it’s a habit. When we treat it as a product—iterating on roles, rituals, and metrics just like we iterate on features—performance compounds, culture strengthens, and growth becomes sustainable.

Inspired by this post on Product School.

November 3, 2025
Upskilling vs. Reskilling: My Playbook to Future‑Proof Teams, Boost Retention, and Ship Faster

In fast-moving product organizations, the skills that got us here won’t carry us through the next wave of change. I’ve learned that future-proofing a team is less about hiring unicorns and more about deliberately growing the skills we already have—and doing it with intention.

Upskilling and reskilling aren’t the same. Knowing the difference can help you build smarter teams and avoid costly missteps in your L&D strategy.

Here’s how I frame it with my leaders: upskilling deepens capability in the role someone already holds—think strengthening discovery, data fluency, or stakeholder management inside an existing lane. Reskilling pivots talent into a new lane—say, a support engineer into data engineering or a product marketer into product operations. Both are essential to building empowered product teams, but they solve different problems.

Deciding which path to take starts with the roadmap and strategy. If your outcomes vs output OKRs signal a need for better execution in current domains, upskilling is the lever. If your strategy introduces new bets—gen AI, privacy-by-design, or a shift to platform architecture—reskilling becomes a strategic investment. I run a simple gap analysis: inventory current skills, map them to near-term outcomes, and identify high-leverage gaps by team.

When I upskill, I prioritize learning in the flow of work. That means structured practice—not just courses—embedded into product discovery, product trios rituals, and code reviews. Shadow sessions, lightweight playbooks, and in-app guides turn new concepts into repeatable muscle memory. For new managers, I add targeted coaching for the IC to manager transition, because role clarity and feedback fundamentals compound quickly.

When I reskill, I treat it like a product launch. There’s a clear charter, staged milestones, a mentor, and onboarding tailored to the new role. I timebox practice projects, use product tours and internal sandboxes, and pair people with forward deployed engineers or senior PMs to accelerate context. The goal is confidence and competence, not just completion.

Measurement keeps the investment honest. I track time-to-productivity during onboarding, deployment frequency and DORA metrics for engineering-heavy paths, and retention analysis for people outcomes. For product and design, I look at decision quality in discovery, reduced cycle time from insight to iteration, and the clarity of written strategy. All of it rolls up into OKRs so learning is tied to business outcomes, not just activity.

The AI wave has made this even more urgent. I’m deliberately upskilling PMs on LLMs for product managers, responsible AI Strategy, and data governance, while reskilling a subset of engineers and analysts into applied gen AI roles. We cover prompt design, evaluation frameworks, and privacy-by-design basics, then ship small internal tools to turn theory into practice.

Culture makes or breaks all of this. I set explicit learning budgets, protect focus time, and model the behavior—publishing my own learning roadmaps and post-mortems. Stakeholder management matters too: I align expectations in QBRs vs OKRs, broadcast progress, and celebrate skill gains the same way we celebrate product wins. When people see that growth is visible and valued, momentum builds.

One example that sticks with me: we reskilled a cross-functional cohort into analytics and experimentation while simultaneously upskilling our existing PMs in discovery synthesis. Within a quarter, decisions got crisper, experiments shipped faster, and collaboration across product trios felt effortless. The compounding effect was unmistakable.

If you’re starting from zero, keep it simple: map the skills you have, the outcomes you need, and choose one upskilling and one reskilling initiative you can deliver in the next 90 days. Make learning visible, measure what matters, and iterate. The teams that master this discipline won’t just keep up—they’ll set the pace.

Inspired by this post on Product School.

November 3, 2025
8 Proven Strategies I Use to Upskill Teams Fast and Future-Proof Our Edge in the AI Era

Your team’s skills have an expiry date. Here’s how to upskill employees before the clock runs out and your edge goes with it.

I’ve learned that upskilling isn’t a one-off training day—it’s an operating system for building resilient, empowered product teams. When we treat learning as a product, with clear outcomes, feedback loops, and constant iteration, we future-proof both our people and our roadmap. Below are the eight strategies I rely on to upskill employees quickly and sustainably while strengthening employee retention and execution quality.

1) Anchor upskilling to strategy and outcomes. I start by mapping critical capabilities to our company strategy and outcomes vs output OKRs. This makes learning unambiguously relevant: every course, cohort, and coaching session ladders up to measurable value. If a skill doesn’t advance our north-star metrics or customer outcomes, it doesn’t make the cut.

2) Build a learning operating system, not a library. Content without cadence is shelfware. I establish a predictable rhythm—monthly skill sprints, short microlearning modules embedded in workflows, and quarterly capability reviews during planning. We integrate upskilling into onboarding, QBRs vs OKRs check-ins, and product roadmapping so learning time is protected, visible, and non-negotiable.

3) Design role-based paths with clear ladders. I create skill matrices for PMs, designers, engineers, and GTM partners, then craft levelled learning paths to close gaps. We use the 70-20-10 model (doing, coaching, coursework) and pair it with individual development plans, so growth is personalized but standardized enough to scale. This clarity boosts motivation and speeds up onboarding.

4) Learn by shipping real value. The fastest learning happens on real products. I pair courses with stretch assignments tied to live initiatives—product discovery sprints, customer shadowing, rapid prototyping with gen ai, and cross-functional product trios. We treat these as safe-to-try experiments with clear success criteria, so teams upgrade skills while moving the roadmap forward.

5) Institutionalize coaching and peer learning. I formalize mentorship, guilds, and weekly critique sessions to turn tacit knowledge into shared practice. We run cross-team demos and communities of practice so lessons travel fast. Managers coach to outcomes, not checklists, and we reward people who teach—because knowledge multiplied beats knowledge hoarded.

6) Measure capability, not attendance. I avoid vanity metrics. Instead, I look for leading indicators that learning is changing behavior and outcomes: higher quality product discovery, clearer product positioning, tighter stakeholder management, improved deployment frequency, and stronger retention analysis. Where appropriate, we set a minimum detectable effect (MDE) for skill experiments to ensure we can actually see impact.

7) Fund time, not just tools. Upskilling dies when calendars are full. I carve out recurring maker time for learning, set explicit expectations in performance plans, and tie promotions to demonstrable capability growth. We provide stipends for courses and certifications, but the real unlock is creating space and manager accountability so learning sticks.

8) Use AI strategically to accelerate practice. We embed AI Strategy thoughtfully: gen ai co-pilots for research synthesis, scenario role-plays for stakeholder conversations, and guided feedback for UX writing and product tours. The rule is simple—AI should compress cycle time and elevate judgment, not replace it. I encourage teams to document prompts and playbooks so good patterns compound.

To align and de-risk, I bring stakeholders into the loop early—finance to co-own ROI, HR to integrate paths into career frameworks, and functional leaders to ensure parity across teams. This alignment reduces friction, strengthens product-led growth, and keeps the effort resilient through reorgs and strategy shifts.

The outcome of this approach is simple: faster time to competency, higher confidence, and a culture where learning is part of how we build. Upskilling is the most durable competitive advantage I know—because tools change, but teams that learn together win together. If your edge feels like it’s slipping, start small, make it visible, and iterate. Your future roadmap—and your people—will thank you.

Inspired by this post on Product School.

November 3, 2025
How I Decode Founder Advice: Lessons from Thumbtack CEO Marco Zappacosta on Boards, Time, and Trust

I recently dug into a conversation with Marco Zappacosta, co-founder and CEO of Thumbtack, who has spent the last 13 years building the company into a billion-dollar business — and it’s his first and only job after graduating college. As someone who lives at the intersection of product management leadership and company-building, I was struck by how deliberately he navigates the deluge of advice that comes with being a first-time founder.

What resonated most was the way he differentiates between moments that demand a return to first principles and those that benefit from a tested playbook. In my own practice, I’ve found that product strategy and organizational design often require first-principles thinking, while operational cadence and execution rituals tend to scale best with proven patterns. The key is recognizing which game you’re playing — invention versus optimization — and applying the right mental models to filter input without losing velocity.

Marco’s approach to parsing counsel as a first-time CEO is refreshingly pragmatic. Rather than treating advice as binary, he triangulates from multiple data points, looks for invariants, and pressure-tests assumptions against the company’s unique context. I use a similar lens: anchor on the problem, map potential solutions to risk/return, and calibrate decisions with base rates where possible. It’s a disciplined way to turn a mountain of opinion into actionable signal — especially when stakes are high.

He also connects this discipline to stakeholder management, particularly in how he runs Thumbtack’s board so quarterly meetings become a critical resource, not just a time suck — and why he shares the board deck with the entire company. I’ve found this level of transparency to be a force multiplier: it aligns teams on priorities, elevates product roadmapping and sprint planning, and empowers leaders to make trade-offs with clarity. When the narrative is shared, accountability scales.

Marco candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to ensure the folks who remained still had confidence in the company and his leadership moving forward. In hard moments like these, consistent communication, explicit prioritization, and a clear framework for decision-making matter more than ever. Trust is built by showing your work — why choices were made, what changes now, and how success will be measured.

Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities. I’ve learned to pair outcome-oriented OKRs with a ruthless weekly schedule audit: if the calendar doesn’t reflect the strategy, the strategy won’t happen. This discipline creates focus, accelerates learning loops, and keeps leaders from becoming the bottleneck.

For builders at any growth stage, there’s a powerful takeaway here: cultivate a repeatable way to distill advice, clarify when to use first principles versus a playbook, operationalize board relationships as strategic assets, and turn time into your sharpest instrument. The result is a more resilient company — and a leadership practice that compounds.

Inspired by this post on First Round.

October 23, 2025
Stop Being the ‘CEO of Culture’: Build Scalable People Systems Like a Product Manager

I keep seeing the same pattern: when people leaders try to be the “CEO of culture,” they stall. When they act like product managers, culture scales. In a recent deep-dive with Colleen McCreary, the Chief People Officer at Credit Karma, I explored exactly how to operationalize that mindset to drive durable results and employee retention at startups.

With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow.

What stood out immediately is her operating system: she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. As a product management leader, this resonates deeply with how we approach product roadmapping and sprint planning, as well as outcomes vs output OKRs — optimize for the majority use cases, make intent unambiguous, and deliver predictably.

She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly. In my experience, this cadence functions like a product release train for your startup compensation strategy — reducing ad-hoc exceptions, creating transparent expectations, and reinforcing fairness. The result is higher trust and healthier decision velocity when headcount scales.

Equally powerful is her reframing of the role itself: she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. That shift unlocks rigorous thinking — requirements, trade-offs, user research, and iterative launches — for everything from onboarding and performance to recognition programs. Treating culture as a portfolio of interdependent systems turns soft notions into measurable, improvable products.

We also examined how rewards and recognition were incredibly different at Zynga and Credit Karma, and why career growth isn’t just about a promotion. I’ve seen teams accelerate growth by expanding scope, deepening skills, and enabling lateral moves — especially during the IC to manager transition — instead of over-indexing on title changes. When you define multiple growth paths, you give top performers more ways to win without distorting your org design.

Finally, we discussed whether to double down on strengths or focus on correcting weaknesses when it comes to performance. My playbook mirrors hers: set outcomes, coach to amplify superpowers, and shore up only the critical deficits that block those outcomes. This keeps the conversation anchored in impact rather than activity and aligns incentives across managers and teams.

If you’re a first-time founder or an early people leader, the takeaway is clear: stop looking for a cultural silver bullet. Build an operating system for people the same way you’d build a great product — define the problems, prioritize, ship incrementally, and measure what matters. When you do, culture stops being a slogan and starts becoming your most reliable growth engine.

Inspired by this post on First Round.

October 23, 2025
Moments That Changed Us: Teresa Torres & Petra Wille on Leadership, Loyalty, and Product Discovery

Some conversations stay with you because they surface the hard-earned truths that quietly shape our judgment as product leaders. This episode of All Things Product with Teresa Torres and Petra Wille is one of those. As I listened, I found myself revisiting my own inflection points—times when prioritization became survival, when loyalty met reality, and when user research humbled my assumptions. What follows are the moments and mindsets I believe every product creator and product management leader can learn from.

Listen to this episode on: Spotify | Apple Podcasts

In this episode, Teresa and Petra swap the stories that shaped their careers. From navigating the fallout of the 2008 recession as a startup CEO, to realizing the company won’t love you back no matter how loyal you are, to the first user interviews that cracked open a new way of seeing product work—these are the pivotal (and sometimes funny) moments that changed everything. As I reflected, I connected these stories to practical patterns we all face: capacity limits that force clarity, leadership under uncertainty, and the discipline of product discovery.

At [02:30], Teresa’s crash course as a startup CEO during the 2008 recession reminded me that there are seasons in product where perfect information doesn’t exist—only direction and conviction. I’ve been there. In those moments, we earn trust by making the next best decision, communicating trade-offs clearly, and moving. That’s leadership when the stakes are real.

By [11:20], the conversation reframed prioritization as survival, not just a backlog exercise. I’ve learned the same lesson: hitting the limits of your own capacity reshapes how you prioritize. It’s not about doing more—it’s about deciding what not to do. In practice, that means aligning roadmaps to outcomes, not output, and letting OKRs focus the team on the few bets that matter now.

At [18:45], Teresa shares the insight that unlocked her agency as a leader: “No one knows the answer.” That line is liberating. When we stop searching for the mythical right answer, we create space for informed bets, time-boxed experiments, and evolving product strategy. I’ve seen teams accelerate the moment they internalize this.

At [29:10], Petra’s story—why the company doesn’t love you back—hits close to home. Loyalty is admirable, but without boundaries it becomes burnout. As leaders, we protect both people and outcomes by setting explicit expectations, designing sustainable on-call and delivery cadences, and recognizing impact early—long before a too-late pay raise tries to fix a deeper problem.

The [42:05] moment about the pay raise that came too late is a textbook example of how retention is a lagging indicator. Compensation, growth paths, and recognition must be proactive. If you wait for exit interviews to learn, you’ve already lost institutional knowledge and momentum.

At [50:15], Marty Cagan and Petra’s first user interviews at Starbucks show how humble, early customer conversations transform practice. Product discovery is not a ceremony; it’s a habit. Even scrappy interviews, when paired with a clear research objective and rapid synthesis, can change a roadmap. I encourage teams to start with simple, recurring conversations and make insights visible in sprint planning.

By [01:02:00], the funny research fail—“close the window” taken literally—delivers the humbling reminder that you are not your user. Language is loaded. Tasks must be unambiguous. And when in doubt, ask one more clarifying question. Every usability study I’ve run has revealed at least one assumption I didn’t know I was making.

Here’s what I took away as a leader and operator: capacity constraints are a gift if we let them focus us; uncertainty is the job, not a blocker; boundaries prevent burnout and build better products; and early, continuous user interviews keep us honest about outcomes over output. If your roadmap isn’t informed by real user context every week, it’s time to change your operating rhythm.

Follow Teresa Torres: https://ProductTalk.org

Follow Petra Wille: https://Petra-Wille.com

Mentioned in this episode: The True Story of Struggles and Success Of A Startup CEO with Teresa Torres by Barry O’Reilly: https://barryoreilly.com/explore/podcast/the-true-story-of-struggles-and-success-of-a-startup-ceo-with-teresa-torres/?ref=producttalk.org

Mentioned in this episode: Petra’s work on coaching product leaders: https://www.petra-wille.com/?ref=producttalk.org

Mentioned in this episode: Marty Cagan: https://www.svpg.com/team/marty-cagan/?ref=producttalk.org

Mentioned in this episode: iPAQ: https://en.wikipedia.org/wiki/IPAQ?ref=producttalk.org

Have thoughts on this episode? I’d love to hear which moment resonated most with you and how it’s shaping your product practice. Share your perspective and let’s learn from each other.

Inspired by this post on Product Talk.

October 22, 2025
Why I’m Tuning In to “In Depth”: Tactical Playbooks for Startup Hiring, Leadership, and Growth

When I first heard, “Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves,” I immediately thought: this is the kind of operating wisdom I reach for every week. As a product leader who obsesses over product management leadership and the realities of scaling teams, I’m drawn to resources that move beyond inspiration and deliver concrete playbooks I can put to work on Monday.

The promise here is refreshingly pragmatic: “We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found.” That’s exactly where the hard problems get solved—whether you’re navigating the IC to manager transition, tuning your approach to product discovery, or tackling employee retention at startups when growth forces you to rewrite the org playbook.

From my vantage point, the most valuable conversations unpack the patterns behind great executive hiring, the cadence of outcomes vs output OKRs, and how storytelling shapes alignment across product, engineering, and go-to-market. I’m eager for insights that translate directly into product roadmapping and sprint planning, lessons on product-market fit that stand up under scale, and founder-led GTM tactics that keep teams focused on what matters.

I’m all in for discussions that get specific—what to ask in a VP interview, how to structure a 30/60/90 for new leaders, and the rituals that keep quality high without slowing velocity. If you’re building, leading, or leveling up your craft, this is time well spent.

I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com

Inspired by this post on First Round.

October 22, 2025
What I Learned from Molly Graham: Hard-Won Management Lessons from Google, Facebook & Quip

I sat down with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School. Every time I revisit her playbook, I find fresh, practical insights that resonate with my day-to-day leading product and scaling teams.

Today, I zero in on management. In my role leading product management at HighLevel, I’ve seen — just as Molly has — how so many startup mistakes come down to general management issues. We unpack the traps that are easy to fall into, how to avoid reactionary leadership, and why deliberate operating mechanisms matter when the team and roadmap are growing fast.

One counterintuitive practice I double down on: spend more time with your highest — not your lowest — performers. Your top talent sets the quality bar, accelerates product discovery, and protects employee retention at startups; investing in them compounds. I share how I structure 1:1s, goal-setting, and outcomes vs output OKRs so high performers stay aligned, unblocked, and energized.

We also talk about managers who shaped our philosophies, the messy IC to manager transition, and the cadence that keeps teams focused without stifling autonomy. Expect concrete tactics you can use tomorrow, whether you’re a first-time manager or a seasoned leader scaling from dozens to hundreds.

Two themes I return to often: codify your culture early, and ‘give away your Legos’. As scope expands, leaders who consciously hand off ownership create more opportunity, reduce bottlenecks, and build a resilient organization. On compensation, I outline a startup compensation strategy and the principles for setting up your first comp system so it’s fair, explainable, and scalable.

If you’re building from 1 to 2, this conversation is a management field guide: clear mental models, practical rituals, and candid lessons learned from scaling product, people, and culture.

Inspired by this post on First Round.

October 22, 2025