Tag: product management leadership

Mastering International Expansion: My Product Playbook Inspired by Faire’s CEO Max Rhodes

International expansion can be a powerful growth lever — or an expensive distraction. Through my product leadership lens, I’m always looking for patterns that separate the former from the latter. Recently, I reflected on insights from Max Rhodes to distill a practical, founder-friendly playbook for going global without losing focus.
Max Rhodes is the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. His vantage point is especially useful for product leaders scaling multi-sided marketplaces and navigating complex cross-border dynamics.
Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar.
In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world.
After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb. I found his decision framework refreshingly practical — a blend of timing, readiness, and strategic focus that maps well to the realities of product-market fit, capital efficiency, and operational maturity. I’ve used similar mental models to pressure-test when our roadmap should shift from depth in one market to breadth across many.
Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it. What resonated with me was the balance between a disciplined operating rhythm — clear goals, tight feedback loops, and cross-functional ownership — and a nuanced, market-by-market go-to-market strategy that respects local competitors and customer behaviors.
To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups I’ve leaned on this mindset during hypergrowth — encouraging PMs, GMs, and functional leaders to continually redesign their roles so we can scale scope without calcifying decision-making. The emotional lift is real, but the payoff is a more resilient organization that can execute across time zones and product surfaces.
Here’s how I translate these lessons into an actionable international expansion checklist for product leaders: validate pull (authentic customer demand and repeatable GTM motion), ensure supply and liquidity for marketplaces, map the competitive landscape by customer jobs (not features), stand up a clear operating cadence with measurable outcomes (not just output-based OKRs), hire for local context and cross-functional ownership, and define a fast, lightweight process for localizing product, pricing, and support. When those pieces click, international expansion compounds rather than distracts.
You can follow Max on Twitter at @MaxRhodesOK.

Inspired by this post on First Round.

October 21, 2025
Never Done Sales? Proven GTM Playbooks I Learned from Meka Asonye at Stripe & Mixpanel

I recently sat down to unpack practical go-to-market lessons with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor. As someone who lives at the intersection of product management and revenue, I was eager to explore how his operator playbooks translate into founder-led GTM, early pilots, customer success, and the first sales hire.

Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business. This trajectory grounded our conversation in the kind of zero to one B2B marketing and sales context that founders and product leaders wrestle with every day.

In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. As I listened, I kept mapping his approach to the product discovery rituals my teams use: clarify the problem in the customer’s words, validate urgency with real-world triggers, and close the loop with crisp next steps. When early calls stall, I look for the same failure modes he flags — muddy ICP definition, solutioning too early, or skipping mutual action plans — because those blind spots ripple into product-market fit lessons later.

He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. I’ve made similar tradeoffs: hire athletes over specialists too soon and you risk inconsistent execution; hire too senior too early and you can overfit process to a still-evolving product. I probe for pattern recognition in discovery, deal hygiene, and collaboration with product — then validate with back-channel references that speak to coachability and grit. On comp, we aligned on anchoring incentives to leading indicators you can measure post-onboarding (pipeline quality, conversion at key stages, and time-to-first-win), rather than chasing lagging revenue alone.

We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. My litmus test: a strong design partner has painful, frequent use cases, access to decision-makers, and a bias toward co-building — without asking you to contort your roadmap into bespoke work. If your ICP is squishy, pilots turn into unpaid consulting; if it’s crisp, you get signal on packaging, onboarding, and the reliability thresholds that unlock renewal.

We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. I see the same pattern: founders over-index on acquisition and underinvest in outcomes. The antidote is early, proactive customer success that operationalizes value moments — onboarding checklists, success plans tied to business metrics, and regular health reviews — so renewal is earned long before it’s negotiated. This is where founder-led GTM compounds, turning hard-won pilots into durable references.

Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture. What stood out to me was the throughline: the same curiosity, discipline, and customer empathy that drive outstanding sales and product outcomes also make for thoughtful investors — especially those helping founders navigate the messy middle between idea and repeatable GTM.

If you’re building from zero, here’s how I’m applying these takeaways with my teams: structure first conversations around problem clarity and next steps; define your ICP tightly enough to say clear no’s; choose design partners who reflect your future ideal customers; treat customer success as a core GTM motion, not a support function; make the first sales hire with leveling discipline and reference rigor; and measure onboarding success with leading indicators that predict revenue. These are the small, repeatable habits that move you from searching for fit to systematizing growth.

Inspired by this post on First Round.

October 21, 2025
IC, Manager, or Founder? Amber Feng’s Playbook for High-Impact, 0→1 Engineering Careers

I recently dove into a compelling conversation featuring Amber Feng, the co-founder and CTO of Cocoon, who was previously an engineering leader at Stripe for eight years. As I reflected on her journey, I found actionable takeaways for anyone navigating an engineering career — whether you’re optimizing your IC craft, stepping into management, or exploring the founder path.

What resonated first was how her experiences span the full spectrum — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. I’ve seen similar arcs on my own teams, and the highest-impact engineers consistently share unexpected traits: they obsess over customer problems, communicate with crisp clarity, manage energy as carefully as time, and treat stakeholder alignment as a core skill. Those behaviors compound across levels, and they’re as valuable in product discovery as they are in product roadmapping and sprint planning.

We also get into the perennial debate many engineers face — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and her experience mirrors what I advise during the IC to manager transition: map your strengths to the type of impact you want to drive. If you thrive on deep focus, complex systems, and technical leverage, the IC path can be your force multiplier. If you’re energized by coaching talent, orchestrating outcomes vs output OKRs, and building cross-functional momentum, management might be your best lane. In either path, revisit the decision periodically — careers aren’t one-way doors.

Another thread I appreciated was how she approaches scope and ownership. Whether you’re shipping as an IC or leading as a manager, momentum comes from framing problems tightly, sequencing bets, and reducing operational drag. I often encourage teams to use a simple try do consider framework to prioritize learning loops, and to treat developer evangelism, forward deployed engineers, and founder-led GTM as strategic tools to accelerate product-market fit lessons.

Finally, we turn the page to the most recent chapter — becoming a first-time founder. Amber shared the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon, and her words of wisdom for engineers with interest in starting their own company from 0 to 1 align with my experience: start with a painfully specific problem, tighten feedback cycles, and keep GTM simple before you scale. Early on, zero to one B2B marketing is about credibility, not campaigns; talk to users, ship obvious value, and let your product creator mindset guide the roadmap.

If you’re exploring co-founding dynamics, you can read the First Round Review article Amber mentioned with the co-founder questionnaire here: https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder

You can follow Amber on Twitter at @amfeng

In sum, whether you identify as an IC, manager, or future founder, the most sustainable careers are portfolio-shaped: evolve your role as your strengths and context change, measure progress by outcomes, and invest in systems that make great work easier to repeat.

October 21, 2025
Executive Hiring That Scales: Battle-Tested Tactics to Find the Right Leaders, Right Now

Executive hiring is one of the highest-leverage — and riskiest — decisions a founder can make. As someone who has scaled product organizations, I’ve learned that the playbook for landing the right leaders changes dramatically as you move from startup to scale. A recent deep dive with Jack Altman, co-founder & CEO of Lattice, crystallized the patterns I see most often: what to prioritize, what to avoid, and how to run a process that consistently produces great executive hires.

The first principle I align with: hire for the next 18-24 months, not the next 5 or 10 years. Early on, the company’s needs shift so fast that long-range “perfect fit” profiles become theoretical at best and paralyzing at worst. I look for leaders who can unlock the next chapter of growth with clear, near-term outcomes — and who have the range to adapt as the strategy evolves. (Here’s the blog post he mentioned about the different stages a CEO faces.)

Founders often get burned by hiring “too big.” Over indexing on BigCo experience or chasing seniority and lofty titles rarely matches the messy, hands-on reality of a startup’s current challenges. I’ve made that mistake — selecting the resume that looked flawless on paper — only to find misalignment on pace, ownership, and scope. Conversely, some of my most impactful leaders started as more junior, undiscovered talent with clear spikes, grit, and coachability. When in doubt, I bias toward the person who shows me how they’ll win here, not just how they won elsewhere.

My end-to-end executive hiring process is intentionally rigorous and replicable. I start by defining the business outcomes we need over the next 18-24 months, then codify them into a scorecard that guides sourcing, interviews, and reference checks. I source via targeted outreach to operators who’ve solved adjacent problems at similarly complex scale. In interviews, I blend behavior-based probes with practical work sessions: “Walk me through how you’d build this team from zero to ten,” “Model the first 90 days,” “Show me the operating rhythms you’ve used to drive outcomes.” I look for crisp thinking, specificity, and an instinct for prioritization under constraints.

References are non-negotiable — and I don’t just confirm facts; I test patterns. I ask backchannels for stories of adversity, the candidate’s default leadership mode under pressure, and how they grew their managers. When stakes are high, I’ll also do references on references to validate consistency. The goal isn’t perfection; it’s reducing variance and surfacing the truth about ownership, resilience, and learning velocity.

There are telltale red flags that an executive lacks an ownership mentality. They blame context rather than diagnose systems. They talk in abstractions without metrics. They focus on headcount before outcomes. They can’t articulate a teachable point of view or how they’d uplevel managers. On the flip side, the strongest candidates connect strategy to execution, quantify trade-offs, and show how they’ll build a high-agency culture from day one.

Most executive hiring errors trace back to fuzzy scope, wishful thinking, or skipping process under time pressure. I guard against this with a 30-60-90 plan tied to measurable leading indicators: decision velocity, operating cadence, pipeline or funnel advancements, hiring throughput and quality bar, and the health of manager layers. If those early signals don’t materialize, I intervene quickly with clarity, coaching, and constraints. And if it still isn’t working, I part ways fast and fairly — the team deserves decisive leadership.

Finally, I’m deliberate about when to promote internally versus hire externally. Internal promotions preserve momentum, culture, and context — especially for IC to manager transition moments — while external hires can inject missing capabilities for new phases of growth (for example, founder-led GTM evolving into a multi-channel motion). I think about the executive team like a portfolio: diversify across experience types, time horizons, and risk profiles. Blend seasoned operators who stabilize systems with high-upside builders who unlock step-changes. That balance is what sustains execution as you scale.

Executive hiring is never “set and forget.” It’s an ongoing discipline of clarifying outcomes, assessing talent against the company’s current chapter, and building the processes that remove luck from the equation. Do that well, and you’ll feel it everywhere: sharper strategy, faster learning loops, and a leadership bench capable of carrying you from startup to scale.

Inspired by this post on First Round.

October 21, 2025
Master Early-Stage Communications: Actionable Lessons from Figma, Uber, and Beyond

Early-stage communication is a product strategy lever, not a press-release afterthought. In my work, I’ve seen the difference a clear narrative makes for founder-led GTM, product discovery, and those early product-market fit lessons that determine whether a company breaks through or stalls. That’s why I was eager to dig into the discipline with someone who’s built communications at category-defining scale.

Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma.

Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden.

Our conversation focuses on what a great communications strategy looks like at early-stage startups. As a product leader, I was struck by how directly the comms fundamentals reinforce core product management leadership behaviors: clarify the customer problem, define the narrative tension, and show proof. She broke down the basics for founders who aren’t familiar with this function, and shared advice for thinking beyond just announcing your Series A funding. I layered on how that same narrative becomes the throughline for zero to one B2B marketing — unifying positioning across product, sales, and customer success.

She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised. I connected this to product discovery: the best message testing mirrors the way we validate hypotheses in product — message pillars, audience-specific proof points, and iterative learning sprints that refine what resonates before you scale paid or earned channels.

Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview. I add a product-centric lens: do the pre-brief like a roadmap review — align on objectives, anticipate risks, prepare crisp artifacts (message map, data, and customer evidence), and practice bridging so you can protect the narrative under pressure.

We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire. My guidance to founders echoes this: hire for strategic clarity first, channel expertise second. In the earliest chapters, a lean, outcomes-focused comms function amplifies founder-led GTM, accelerates learning cycles, and compounds trust with customers, candidates, and investors.

If you treat communications as an extension of product — a disciplined system for discovering, validating, and scaling the narrative — you’ll see compounding returns. That mindset aligns your story with your strategy, makes every launch a proof point, and turns early momentum into durable market position.

Inspired by this post on First Round.

October 21, 2025
Master Startup Compensation: Proven Tactics for Offers, Equity, and Retention at Every Stage

Compensation is one of the most emotionally charged and strategically consequential decisions a startup makes. I recently dug deep into this topic with Kaitlyn Knopp, founder and CEO of Pequity, which automates HR workflows to make compensation more equitable and scalable. Her perspective resonated with my own experiences leading product teams, where pay clarity, fairness, and speed can make or break hiring and retention.

Prior to starting Pequity, Kaitlyn built compensation programs and teams at companies like Instacart, Cruise, and Google — bringing a deep well of experience to this often complicated topic. That breadth matters: startup compensation strategy must evolve as you move from zero to one, to scale, and then to sustained growth.

For founders making their first hires, I emphasize the same traps Kaitlyn flagged: ad hoc offers, one-off exceptions, and over-indexing on negotiation. Instead, I recommend a lightweight framework anchored in broad levels and an initial comp philosophy. This early scaffolding doesn’t need to be heavy or bureaucratic; it simply needs to be explicit enough to guide consistent decisions and communicate how salary, equity, and performance will work for the next 12–18 months.

On offers, I take a balanced view of negotiating. There are pros and cons to negotiating offers, and over-negotiation can quietly erode internal equity and manager confidence. Rather than endlessly debating base salary, I lean on creative approaches outside of salary — such as the exercise window — to tailor offers within guardrails. And because many candidates (especially those who’ve never worked at a startup before) struggle to value equity, I always include a simple equity one-pager: how vesting works, potential outcomes, and what risk actually means in practice.

As the company grows quickly, new challenges appear. Retaining existing employees requires intent, not improvisation. Equity refreshes are a powerful tool when tied to impact and market realities. I also pay close attention to the psychology of bonuses — they can motivate or misfire depending on timing, frequency, and clarity. During periods of inflation and salary adjustments, I favor a transparent narrative that connects the market, our compensation philosophy, and the choices we’re making this cycle.

There’s a tempting trend toward highly individualized packages. While flexibility has its place, I’ve found that too much customization introduces hidden inequities and ongoing operational drag. The antidote is education. I invest in helping employees fully understand their comp — not just the headline numbers. That means straightforward walk-throughs of dilution and tax considerations, so folks see the real value and trade-offs over time.

Here’s how I operationalize this playbook with my team: we publish a clear compensation philosophy; define broad levels and salary bands; standardize equity grant guidelines with built-in refresh logic; and formalize an offer review process to prevent one-off exceptions. We also equip hiring managers with candidate-facing materials to explain equity, stock options, the exercise window, vesting schedules, and potential scenarios. This reduces confusion, accelerates decision-making, and builds trust.

For ongoing discipline, I treat compensation like any other critical product system: we set review cadences, define decision rights, audit for pay equity, and proactively monitor market signals. When we do run compensation changes (promotions, adjustments, bonuses), we pair them with simple, empathetic communication so employees understand the why behind the change — not just the what.

No matter your stage, the goal is consistent and comprehensible startup compensation: an initial comp philosophy you can defend, offers that reflect both market and mission, and retention mechanisms that honor impact. Do these well, and you’ll ship faster, hire better, and keep your highest performers engaged for the long haul.

Inspired by this post on First Round.

October 21, 2025
Cracking Government Sales: Lessons on Long Cycles, Risk, and Pivoting to Product-Market Fit

Working with public-sector buyers is a different sport than traditional enterprise sales, and I’ve learned that getting it right demands rigor, patience, and empathy. That’s why I was eager to dive into the realities of selling into government with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. The conversation sharpened my own playbooks for B2G sales and underscored how product management leadership must adapt when the buyer is a city, county, or state agency.
We unpacked the practicalities of going to market with government: the extra-long sales cycles, layers of subcontractors, and the need to convince risk-averse decision-makers to take a chance on a startup. In my experience, this requires founder-led GTM early on, paired with meticulous stakeholder mapping, procurement fluency, and airtight compliance. I’ve found it’s crucial to identify the economic buyer, policy owner, legal gatekeeper, and program operator—and then multi-thread relationships so momentum isn’t lost when a champion rotates roles or a budget committee delays.
When cycles stretch into quarters or years, I put a premium on structured pilot design. I aim for time-boxed proofs of value with clear milestones, measurable policy outcomes, and deliverables that de-risk adoption for the agency. This approach aligns incentives for forward progress, while giving the vendor room to iterate on product discovery without jeopardizing trust. It also creates a shared narrative that risk-averse decision-makers can carry into internal approvals.
We also took a step back to traverse the winding road that led to Promise in its current form. Like so many founders I’ve advised, the early journey involved recalibrating the problem-solution fit. Phaedra explains the signals that the first iteration of the product, a bail reform platform, wasn’t going to work as she’d hoped. Her experience mirrors what I watch for in my own teams: leading indicators such as stalled deployments, low utilization by the primary user, misaligned unit economics in government procurement, or policy constraints that cap impact despite strong intent from stakeholders.
From a product-market fit lens, the lesson is to separate mission conviction from mechanism flexibility. Keep the mission constant, but be ruthless about pivoting the mechanism when evidence stacks up. For me, that means codifying hypotheses, setting explicit kill/commit thresholds, and running rapid, qualitative cycles with front-line operators. In the public sector, small usability frictions often become policy blockers—so I test workflows in the field, not just in demos, and pressure-test compliance, data-sharing agreements, and funding sources during discovery, not after.
For founders navigating a pivot, I recommend three disciplined moves: narrow the value proposition to a single, high-frequency pain; re-sequence your GTM around the budget line item that actually funds the work; and redesign onboarding to deliver a visible win inside one reporting cycle. These moves increase the odds of institutional buy-in and compress the time to proof points, even amid long procurement paths.
Ultimately, selling to government rewards clarity, credibility, and outcomes over output. The path is slower, but when you align your roadmap to measurable public impact—and build trust with the program staff who carry the day-to-day load—you create durable, compounding value. That’s where founder-led GTM, rigorous product discovery, and a willingness to pivot converge into true product-market fit lessons for the public sector.

October 21, 2025
How I Build Highly Technical Enterprise Products: Hard-Won Lessons from CockroachDB and Nate Stewart

Building a highly technical enterprise product is as much about disciplined focus as it is about engineering excellence. When the stakes include mission-critical uptime, data integrity, and scale, the product decisions we make today compound for years. That’s why I’m constantly looking for patterns that help my team make fewer, better choices.

Recently, I sat down with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. Our conversation crystallized a number of principles that I’ve seen work in my own practice and that I believe every enterprise product leader should internalize.

First, focus starts with a brutally specific use case. Nate walked through how the Cockroach team narrowed the aperture on where their database would be irreplaceable, not just incrementally better. That clarity anchored the go-forward plan — which meant saying no to a lot of customers who didn’t align with the product roadmap. In my experience, this is the hardest muscle to build. I’ve found it helpful to articulate a one-sentence “non-negotiable” use case, followed by a short list of adjacent use cases we’ll explicitly defer.

Second, treat over-commitment as a structural risk. Nate dives into the tactical ways to avoid taking on too many customer commitments, which he calls tech debt for product teams. I track this debt explicitly: a ledger of promises, effort estimates, and the strategic rationale for each commitment. We cap the total “commitment points” per quarter, require a written business case for any exception, and sunset low-impact promises with transparent communication. This keeps the roadmap credible and prevents well-intentioned deals from silently hijacking strategy.

Design partnerships are the force multiplier in deeply technical categories — especially when working with conservative enterprise clients. Nate outlined different types of design partners and why you should have all of those represented in the early days of your startup. I map partners along two axes: ambition (visionary to conservative) and environment (startup to regulated enterprise). A healthy portfolio includes at least one of each: a visionary who pushes the frontier, a pragmatic mid-market partner who validates repeatability, and a regulated enterprise that stress-tests compliance, security, and operability.

To make design partnerships work, I rely on a simple operating contract: shared problem statement, measurable outcomes, and mutually agreed constraints. We align on exit criteria before we start, time-box pilots, and avoid bespoke code unless it is clearly on the critical path to the broader product-market fit. Executive alignment on both sides and weekly joint reviews keep momentum high and surprise low.

For product leaders stepping into a new role, nothing matters more than building a rock-solid partnership with a CEO as the first head of product. I’ve found three habits indispensable: a shared narrative (why we win), a living strategy doc (how we win), and a predictable cadence (when we decide). I send pre-reads before our 1:1, frame trade-offs in terms of risk and reversibility, and use disagree-and-commit to keep the organization moving. This creates trust, speeds decisions, and shields teams from thrash.

Finally, I’m intentional about how I solicit honest feedback across the executive team. I rotate a “red team” to stress-test critical bets, run brief anonymous pulses after major launches, and host cross-functional postmortems that focus on outcomes vs output. I also schedule regular skip-level interviews to uncover operational friction that might never surface in leadership meetings. These mechanisms create a continuous learning loop without slowing down the business.

In sum, the craft of enterprise product management lives at the intersection of clarity, constraint, and collaboration. Define a use case so sharp it excludes most opportunities. Manage customer promises like a portfolio of risk. Build a diverse, intentional set of design partners. And invest early in executive alignment and feedback channels that scale with your ambitions. That’s how we turn technical excellence into durable enterprise value.

October 21, 2025
Stop Promoting Your Top ICs: “When They Win, You Win.” Lessons for Modern Managers

I’m often asked what truly powers a high-performing product organization. My answer starts with managers. That’s why I was eager to revisit the work of Russ Laraway, a seasoned leader who’s been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital. His career arc mirrors the kind of product management leadership many of us strive to cultivate on our teams.
He’s written a new book, titled: “When They Win, You Win.” It’s a research-backed guide that resonated with me because it balances practical tools with the nuance required for the IC to manager transition inside fast-moving product teams.
One idea that immediately stood out is how broken the manager selection process often is. Too many companies default to promoting the highest performer, rather than looking for folks who explicitly demonstrate leadership chops. In my own teams, I’ve seen elite individual contributors struggle when asked to lead without preparation. We now assess for behaviors like an ability to set clear outcomes (not just outputs), coach consistently, give and receive actionable feedback, and create clarity during ambiguity—before offering the role.
Equally valuable are the raw ingredients Russ outlines to gauge whether someone’s truly ready for management—even if they weren’t the best individual contributor. I’ve learned to look for three signals in promotion and hiring loops: (1) a habit of elevating peers’ work, (2) structured thinking that translates strategy into weekly execution, and (3) a bias toward accountability paired with empathy. If you’re hiring managers from outside the company, build your interview plan to suss out the right hire. I like questions that probe how candidates set outcomes vs output OKRs, run 1:1s that compound performance, and handle underperformance without losing team trust.
The book synthesizes heaps of research into clear management frameworks I can put to work immediately. One takeaway is a practical list of the behaviors of highly-engaging managers. What’s worked for me: weekly 1:1s anchored on priorities and growth, explicit role clarity, lightweight career conversations every quarter, strengths-based recognition tied to outcomes, and crisp decision rights. When managers consistently do these basics well, engagement rises and product velocity follows.
There’s no shortage of management advice out there—often contradictory. What I appreciate here is the distillation into an essential, research-backed guide for the modern manager that cuts through the noise. The result is a repeatable playbook I can hand to new product leads and know they’ll have the foundations to build trust, set direction, and deliver business impact.
You can follow Russ on Twitter at @ral1.
His book, “When They Win, You Win.” comes out on June 7, 2022. For more details, see the Amazon listing: https://www.amazon.com/When-They-Win-You-Manager/dp/1250279666.

October 21, 2025
From PM to VP: Proven Tactics to Accelerate Your Product Career and Lead with Confidence

I’ve spent my career growing product teams and coaching product managers, and I’m continually drawn to leaders whose playbooks translate across company stages. One standout is Jiaona Zhang (she goes by JZ), whose journey offers an especially clear roadmap for moving from individual contributor to executive product leadership.
JZ is the VP of Product at Webflow. Before that, she was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems. She teaches product at Stanford and mentors rising product leaders. You may also know her for the widely shared article, “Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products).”
What resonates most with me is her framing of the product career path. Instead of a linear ladder, think of three distinct phases: contributing as a PM, managing PMs, and leading the function. I’ve used a similar model to guide my own teams, and I’ll walk through how I apply this framework in practice.
Phase 1 — The PM role: When you’re breaking into product, focus on environments that will compound your learning. I look for signs of strong product discovery, clear ownership of product roadmapping and sprint planning, and a culture that values outcomes vs output. In interviews, I ask how success is measured (OKRs, customer outcomes, adoption) and how PMs partner with engineering and design. Early mistakes are common: trying to own decisions without owning the problem, shipping features without a minimum lovable product mindset, and confusing velocity with value. To avoid these traps, anchor your work in customer problems, link every roadmap item to measurable outcomes, and practice crisp storytelling that connects strategy to execution.
Phase 2 — The managing phase: The IC to manager transition is a shift from doing the work to building the system that does the work. As you become more senior, zoom out from features to portfolios, from experiments to strategy. When hiring, I look for complementary archetypes across the team — the product creator who thrives in zero-to-one, the operator who scales repeatable playbooks, the analyst who brings rigor to prioritization, and the evangelist who aligns stakeholders. For first-time managers, my advice is to establish clear decision rights, define the bar for product quality, and coach toward autonomy. Balance mentoring with mechanisms: weekly product reviews, outcomes-driven OKRs, and lightweight rituals that reinforce clarity without micromanaging.
Phase 3 — The executive phase: At this stage, I treat the product organization itself as a product. Define a vision, clarify the customer (your CEO, exec peers, board, and of course end users), and build feedback loops. With the CEO, align on the narrative, business model bets, and the handful of company-level outcomes that matter most. With peers on the exec team, drive cross-functional planning so GTM, finance, and product are synchronized around impact, not just output. With the board, translate strategy into measurable progress and risk mitigation. The goal is to ship strategy: clear choices, intentional sequencing, and a portfolio that advances product-market fit and durable growth.
Whether you’re trying to break into product, grow into management, or step into the executive arena, this three-phase arc is a reliable compass. Invest in product discovery, tie work to outcomes, and develop the operating cadence that turns intent into impact. That’s how you accelerate from PM to VP — and lead with confidence at every step.

Inspired by this post on First Round.

October 21, 2025
Why the COO Role Is the C-Suite’s Most Fluid: Archetypes, No-Blame Culture, and CEO Guidance

I’ve long believed the COO seat is the most fluid role in the executive suite, and my perspective has been sharpened by learning from operating leaders who’ve scaled iconic companies. One conversation that stands out centers on Sara Clemens, most recently COO of Twitch and former COO of Pandora.

In this interview, we explore the nuances of the COO role, which can vary drastically across different companies. We cover:

The three main COO archetypes and which sorts of folks are best suited for those roles.

The tactical elements of being a COO, including Sara’s advice for what good strategy actually looks like, and how to truly create a no-blame culture.

Sara’s lessons on keeping pace as a company doubles in size, including her tips on sketching out “decision rights.”

Guidance for CEOs considering bringing on a COO to the executive suite.

From my vantage point in product management leadership, the variability of the COO mandate is a feature, not a bug. Great COOs adapt to the business model, stage, and CEO superpowers. The best partnerships I’ve seen start with explicit clarity: What outcomes matter most in the next 12–18 months? Which constraints are real? Where will product, operations, and go-to-market intersect—and who owns what?

On archetypes, I map product’s needs to the operator’s strengths. If we’re pursuing step-function growth, I look for a COO who is comfortable orchestrating ambiguous, cross-functional bets. When the priority is scaling reliability and margins, I align with a process- and systems-oriented operator. When the goal is organizational transformation, I look for a builder who can reset norms while protecting momentum. Getting this fit right improves execution, reduces decision latency, and clarifies how we measure progress.

On the tactical elements of being a COO and what good strategy looks like, I anchor on a few principles that have never failed me: strategy is a coherent set of choices, not a list of initiatives; it prioritizes outcomes over output and forces trade-offs. We translate those choices into a focused operating cadence—clear goals, crisp leading indicators, and reviews that separate signal from noise. In practice, that means elevating outcomes vs output OKRs, pressure-testing assumptions early, and linking roadmaps to measurable value creation.

Creating a no-blame culture isn’t soft—it’s operationally essential. Blame keeps teams defensive; learning keeps them fast. I’ve had success institutionalizing blameless postmortems, pre-mortems for high-risk launches, and a norm of writing down hypotheses before we run experiments. We fix the process, not the person. Over time, this builds psychological safety and enables the honest retrospectives that high-velocity product and operations teams depend on.

As companies double in size, complexity compounds. This is where “decision rights” become a force multiplier. I recommend codifying who is the decision-maker, who must be consulted, and who needs to be informed before work begins. Whether you prefer RACI, DACI, or RAPID, choose one, teach it, and use it consistently. Pair decision rights with single-threaded ownership for critical initiatives and you’ll reduce escalation churn, speed handoffs, and preserve accountability as headcount grows.

Keeping pace during hypergrowth also demands an operating rhythm that scales. I align quarterly planning with a lightweight monthly business review, ensure product roadmapping and sprint planning tie directly to company-level outcomes, and maintain a disciplined change-management channel so emergent priorities don’t derail committed work. When the cadence is consistent and the artifacts are simple, leaders can move fast without breaking trust.

For CEOs considering bringing on a COO to the executive suite, my guidance is straightforward: define the mandate in terms of outcomes, not tasks; be explicit about the seams between CEO, COO, and product; and decide how you’ll make decisions together before the first decision. Align on metrics, communication rhythms, and escalation paths. Hiring a great COO is not about finding a clone—it’s about designing a complementary partnership that compounds your strengths and closes your gaps.

The through line across all of this is clarity—of strategy, of responsibilities, and of learning. Get those right, and the natural fluidity of the COO role becomes your organizational advantage.

October 21, 2025
Go Totally Asynchronous: Inside Sidharth Kakkar’s Remote, Autonomous Culture That Scales

I’ve spent years leading product teams across global B2B SaaS, and few topics spark more debate than building a remote team that operates totally asynchronously. Recently, I revisited the playbook of Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.)

Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a repeat founder, Sidharth picked up a ton of valuable lessons, particularly when it comes to company culture and management.

Right from the start, he knew he wanted to build Subscript to be global, distributed, and asynchronous. That’s why there are no internal company meetings. Everyone also operates autonomously, deciding what to work on for themselves.

In this analysis, I dive into both the philosophy behind this unique approach and the nitty gritty details of how exactly it works in practice. I’ll unpack how to share company updates asynchronously every week; advice on how to approach goal-setting and performance feedback while minimizing micromanagement; tips for improving transparency and documentation, plus details on Subscript’s running product/market fit journal; thoughts on how to assess asynchronous communication skills when hiring; and how this culture impacts a founder’s role and schedule.

On weekly updates, asynchronous communication shines when it is consistent, structured, and outcomes-focused. I recommend a lightweight cadence that combines a written executive summary, links to artifacts (roadmaps, PRDs, dashboards), and optional short Looms for rich context. Tie each update to outcomes vs output OKRs so teams self-calibrate without meetings, and make updates searchable so new hires can ramp themselves with a clear trail of decisions and tradeoffs.

For goal-setting and performance feedback, autonomy and clarity must coexist. Define clear success metrics upfront, timebox discovery, and use product roadmapping and sprint planning rituals that emphasize measurable customer outcomes over task completion. Replace micromanagement with transparent expectation docs, written performance narratives, and asynchronous 360 feedback—so individuals know what good looks like and can course-correct without waiting for a meeting.

Transparency and documentation are the backbone of a remote, autonomous culture. Centralize decisions in a single source of truth, standardize decision records, and maintain a living discovery log alongside Subscript’s running product/market fit journal. This practice compresses feedback loops, preserves institutional memory, and accelerates product discovery by making assumptions, experiments, and results easy to consume across time zones.

When hiring, I prioritize asynchronous communication skills as first-class selection criteria. Use written work samples, time-boxed take-home prompts, and collaborative docs to evaluate clarity, rigor, and empathy in writing. Look for signal such as strong structuring, crisp problem statements, thoughtful tradeoffs, and proactive documentation of risks and unknowns—capabilities that predict success on distributed teams.

This culture fundamentally reshapes a founder’s role and schedule. With deep work protected and status noise automated, leaders can spend more time on strategy, customer conversations, and coaching. Decision latency drops because context is captured in writing, and the organization scales through principles rather than approvals—exactly what you want in a high-trust, high-leverage product operating system.

There’s tons of food for thought in here, whether you’re a founder thinking about shaping your company culture, or a manager looking for some fresh ideas.

Inspired by this post on First Round.

October 21, 2025