Tag: IC to manager transition

Inside the Engineering Cultures of Microsoft, Reddit, Looker & Twitter: Hard-Won Lessons

I’m endlessly fascinated by how engineering culture shapes product velocity, quality, and leadership outcomes. Drawing on lessons from Nick Caldwell’s journey, I’ve distilled the practices that consistently produce performance, clarity, and cohesion across teams. These are the ideas I reference when coaching product and engineering leaders, building org structures that scale, and aligning teams around outcomes.

Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.

Across Microsoft, Reddit, Looker, and Twitter, the cultural contrasts are stark—and incredibly instructive. I focus on how each environment sharpened a different leadership muscle: designing resilient organizations, navigating high-context communities, aligning product and engineering at scale, and translating mission into execution. The net effect is a practical playbook for product management leadership, manager development, and cross-functional collaboration.

From Microsoft, I take to heart what Nick believes is a massively underrated approach to organizational design. The company’s disciplined cadence of regular pruning and shaping the org chart keeps accountability crisp and prevents drift. Their management training and talent development systems create durable leadership pipelines, while what Nick calls the fairest performance review system he’s seen sets a predictable bar for growth. In my own practice, I mirror these principles with explicit role charters, outcomes vs output OKRs, and routine structure audits that keep teams mission-aligned.

Transitioning from a 15-year tour at Microsoft to Reddit came with a steep learning curve—and that resonates deeply with anyone making a big career move or an IC to manager transition. Nick’s advice maps closely to what I coach: re-anchor on the company’s narrative, over-communicate intent, and recalibrate decision speed to the culture. At Reddit, the mission-driven culture isn’t just branding; it informs how influence is earned and how leaders show up. That lens carries forward to leadership at Twitter, where connecting daily execution to mission keeps product and engineering grounded and resilient through change.

Looker offered a rare vantage point: leading both product and engineering. The result is a masterclass in reducing friction between two orgs that are often at odds. The insights I apply: define a single operating rhythm for product roadmapping and sprint planning, eliminate ambiguous ownership, and measure joint outcomes rather than siloed outputs. When product strategy, discovery, and delivery operate on one shared cadence, you unlock faster decisions, fewer handoffs, and cleaner accountability.

For managers looking to level up, these lessons are actionable: invest in management training, make performance systems transparent, prune org complexity before it compounds, and tie every roadmap bet to mission and measurable outcomes. For engineers eyeing leadership, study how culture sets the rules of engagement—then learn to translate that into decision frameworks, communication habits, and hiring signals that reinforce your product and engineering alignment.

This is a wide-reaching set of takeaways because the problems are universal: how to design organizations that scale, grow leaders systematically, and build cultures where product and engineering don’t just coexist—they compound each other’s strengths. If you’re rethinking your org chart, refining your OKRs, or preparing for your next leadership transition, these practices will give you a durable edge.

Inspired by this post on First Round.

October 21, 2025
Retaining Startup Talent: Conflict Playbooks and Couples Therapy Tactics I Use

I recently sat down with Alex Buder Shapiro, the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care. As someone who leads product management and cares deeply about culture, I wanted to unpack what truly keeps startup employees engaged and growing over the long haul — and how people leaders can partner with product leaders to make that happen.

Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled. That vantage point matters: when HR business partners and product leaders operate as one team, we can proactively design the org, clarify decision rights, and align incentives so people can do the best work of their careers.

We began with conflict resolution at work — a topic that shows up in every scaling startup. Alex talked through patterns she’s seen and why borrowing from couples therapy can be surprisingly effective. I’ve found the same. Techniques like mirroring to ensure each person feels heard, naming feelings before jumping to fixes, and agreeing on shared norms (“assume positive intent,” “disagree and commit,” “no surprises”) defuse tension fast. When I coach PMs and cross-functional leads, I push for structure: time-boxed turn-taking, clear owners for decisions, and a quick retro to repair after conflict. These are the same muscles healthy relationships use — empathy, curiosity, and accountability.

We also dug into the challenge of getting employees to stick around long-term at startups. Retention is rarely about perks; it’s about momentum, meaning, and mastery. From hiring your own boss to navigating tough career conversations, Alex’s playbook resonated with mine. I encourage leaders to draft a “growth contract” with each team member: What capabilities are you building this quarter? What scope will expand if you nail it? What support do you need? When someone hires their own boss, I frame it as a capability accelerator — you’re trading title for a teacher, and the compounding effect on your craft can be huge.

Her own journey — rising through the ranks from IC to exec at Flatiron — offers a blueprint for the IC to manager transition many product folks face. My guidance: don’t rush the leap. First expand scope as an IC (own bigger outcomes, not just features), then practice leadership without authority (drive cross-functional programs), and finally formalize people leadership when the org truly needs it. In product management leadership, that sequencing prevents the common trap of managing without mandate or mission.

Alex has also seen the growing pains of scale up close — and I’ve lived them, too. On day one in a new role, you’re “selling” your new role with an elevator pitch when you first join, because clarity reduces friction. I write a crisp one-liner on why the role exists, the problems it owns, and how success will be measured, then socialize it relentlessly. Just as important is resisting the danger of locking into people processes and frameworks too early. I favor lightweight experiments: pilot a performance ritual with one org, run a compensation calibration dry run, or test a feedback cadence in a single squad before scaling. Evolution beats edict.

Across all of this, the throughline is simple: great people leadership and great product leadership share the same foundation — clear outcomes, frequent feedback, and respect for the human at the center of the work. Whether you lead engineering, design, product, or people, these principles help teams compound trust and results.

Inspired by this post on First Round.

October 21, 2025
Mastering Operational Complexity: Building Thirty Madison Without Upside-Down Unit Economics

Operationally-intensive businesses can be unforgiving if you don’t design for unit economics from day one. That’s why I was eager to dig into the playbook behind Thirty Madison and its approach to marrying operational excellence with disciplined financial fundamentals.

I sat down with Steve Gutentag, the co-founder and CEO of Thirty Madison, a healthcare company focused on widening access to specialized care for chronic conditions. The company’s product and operations choices offer a compelling case study for product leaders who need to scale real-world services without sacrificing margins or customer experience.

After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps, a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation.

We got into the realities of building an operationally complex business with a physical or real-world component. I’ve led product and operations through similar constraints, and I appreciated how Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build. The throughline: pair a crisp problem definition with an operating model that earns its margins every day.

He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale. In my experience, this is the difference between a growth engine and a leaky bucket.

We then moved to team design — the people mechanics that make operational complexity manageable. In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager. I shared my own approach: probe for judgment under ambiguity, appetite for continuous improvement, and the discipline to instrument every step of the customer journey.

My takeaway for product leaders: treat operations as a first-class product. Pressure-test the model with conservative assumptions, validate every cost driver, and identify the inventive moves that unlock margin at scale. Keep the customer experience and the P&L in the same conversation, and hire operators who think like product managers and product managers who respect operational constraints. That’s how you build an operationally-intensive business without ending up with upside down unit economics.

Inspired by this post on First Round.

October 21, 2025
Product Lessons from KiwiCo: Scaling Physical Products, Toddler Feedback, and Manager Training

I sat down with Sandra Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. After executive roles at PayPal and eBay, she started KiwiCo over ten years ago to give her own kids more hands-on projects to exercise their creativity — a spark that led to entrepreneurship. Today, KiwiCo has expanded to include 8 different lines of crates that are shipped out monthly. As a product creator, I was eager to unpack how she turned a personal need into a scalable, beloved physical product line.

We dug into the thornier challenges of building physical products and her biggest aha moments as a first-time founder. She described creating the first KiwiCo crate — from the product development process to spinning up a supply chain and shipping department. We discussed how KiwiCo approaches new product lines, particularly in the last year when KiwiCo demand skyrocketed. She also shared how the team gathers quality consumer feedback when your customer is often a toddler — an audience that demands observational research, short feedback loops, and thoughtful proxies through parents and caregivers.

From a product discovery perspective, I found KiwiCo’s approach refreshingly pragmatic: iterative prototyping, tight learning cycles, and early validation that inform product roadmapping and sprint planning. When demand surges, operational excellence becomes a product feature — and Sandra’s experience reinforced that product-market fit lessons don’t end at the moment of traction; they expand into forecasting, inventory strategy, and resilience across partners. The throughline is an outcomes-over-output mindset that keeps the team anchored on value delivered to families rather than feature velocity.

We then shifted to culture — the often overlooked engine behind durable execution. Sandra is a strong believer in manager training for everyone, from folks that manage just one person to executives that have been managing for decades. She outlined the specific management training modules they leverage at KiwiCo and made the case for having everyone at the company fill out a motivations spreadsheet. For leaders navigating the IC to manager transition, these guardrails accelerate consistency, empathy, and decision quality across teams.

Finally, we explored how she creates a feedback-rich environment for herself as a CEO. I appreciated the intentionality — structured forums, explicit invitations for critique, and clear norms that make feedback safer and more actionable. Whether you’re shipping crates or software, the lesson holds: sustained product management leadership depends on mechanisms that convert diverse signals into aligned action. If you’re building physical products or scaling a product organization, these practices offer a blueprint for learning faster, de-risking complexity, and keeping customers — even the tiniest ones — at the center.

Inspired by this post on First Round.

October 21, 2025
Cracking Executive Hiring: My Playbook from Robinhood COO Gretchen Howard on Interviews & Onboarding

I recently sat down with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund. That lens—hypergrowth, scale, and rigor—made for a candid, deeply practical conversation about the art and science of executive hiring.
My first principle: align the hiring profile to the trajectory of the business. Before I draft a role spec, I map where the company will be in 12–24 months and work backward—org design, critical outcomes, decision rights, and the interfaces this leader must own. This prevents over-hiring for prestige or under-hiring for comfort, and it keeps us investing in the right places where leadership leverage is highest.
We also dug into the balance between domain and operating DNA. For certain roles, industry context matters, but in high-velocity environments I prioritize builders who can scale ambiguity into systems. Put differently, I look for leaders capable of balancing financial industry expertise with an innovative, hands-on mindset that’s critical for startups. That balance avoids the two common failure modes: executives who can “talk the talk” but can’t ship, and specialists who struggle once the playbook runs out.
On the executive interview process, I keep a tight loop that tests judgment, learning velocity, and execution. I probe for whether someone has a “knower” versus a “learner” attitude by asking for specific instances where they reversed a strongly held view based on new data, what broke when they scaled from one stage to the next, and how they built successor benches. I also ask candidates to walk me through decisions they owned end-to-end—the context, options considered, trade-offs, and how they measured outcomes.
My feelings toward interview exercises are intentionally mixed. Over-engineered “strategy cases” can select for presentation polish over operating truth, yet lightweight, job-relevant exercises can surface depth and working style. I time-box collaborative work sessions on a real (sanitized) problem we’re facing, making expectations explicit: I’m evaluating how we think together, not a perfect answer. This yields a more authentic read on communication, prioritization, and bias-to-action.
Reference checks are non-negotiable and high-signal when structured. I run both provided and backchannel references, triangulating on scope, followership, and change management. My go-to questions: What did this leader make better that stayed better? How did they handle a miss? Would you rehire them for this stage and why? I also ask references to predict the candidate’s most likely struggle in the first 90 days; those predictions often become my onboarding guardrails.
Even great hires can fail without intentional onboarding—what I call preventing “organ rejection.” I co-create a 30/60/90 plan that includes outcomes, decision rights, and the first 10 relationships to cement. We align on a cultural narrative (how we build, decide, and escalate), clarify non-negotiables, and schedule fast feedback loops at weeks 2, 6, and 12. Success here looks like early, compounding wins and a clear rhythm with peers—before muscle memory hardens in the wrong direction.
If you’re struggling with your executive hiring—whether it’s coming up with the right candidate profile, aligning on culture fit, or finding that your interview process doesn’t seem to be surfacing the best candidates—this playbook will help you de-risk the decision. The combination of a stage-appropriate profile, a learning-oriented interview loop, disciplined reference checks, and deliberate onboarding dramatically increases the probability that your next executive hire will unlock leverage instead of friction.

October 21, 2025
From Founder to CEO: Executive Coach Alisa Cohn on Candid 360 Feedback and Growth

I recently dug into a powerful conversation with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week, and it’s a timely playbook for anyone navigating the shift from founder to CEO.

What resonated most with me is how central self-awareness is to startup leadership—and how hard it is for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa highlights both the right questions to ask and how to get at the root of what people are actually saying in their feedback. In my own practice leading product management, I’ve learned that a multi-source feedback loop is non-negotiable if you want to grow faster than your company’s complexity.

To invite real candor, I set clear expectations up front, guarantee anonymity when appropriate, and ask for specific examples. Prompts I rely on include: What should I start, stop, and continue? When have I been most and least effective? What’s one behavior that would most improve my impact? I also ask for a confidence rating and context (e.g., cross-functional vs. team settings), which surfaces patterns that one-off comments miss. This simple structure keeps feedback actionable for product management leadership and founder-led GTM environments where speed can mask weak signals.

Of course, the hardest part is what to do with what you hear. Not every piece of feedback is useful, and Alisa’s guidance aligns with my own rubric: look for themes across sources, weigh input by proximity to the work and blast radius, separate facts from feelings, and test changes through small, time-boxed experiments. I operationalize changes in my day-to-day routine with calendar nudges, pre-commitments (e.g., publish decision criteria before important calls), and a trusted peer who can observe and nudge me in real time. Small, consistent behavior changes compound faster than sporadic big swings.

We also surface the most common opportunities for growth that show up again and again: communication and decision-making. I’ve seen how a CEO’s personality is unconsciously reflected in the company culture—pace, rigor, appetite for risk, how we treat “no,” and whether we bias toward outcomes vs output. To counter the “shadow of the leader,” I make these drivers explicit: write down decision guardrails, publish decision logs, and define what “good” looks like for communication quality and speed across functions.

Another area we dig into is how to have effective conversations about layering and letting people go. Layering—bringing in experienced leaders above early high performers—works when expectations are clear, roles are well-scoped, and dignity is preserved throughout. My playbook: share the business rationale, define success metrics and timelines, offer a growth path where possible, and avoid ambiguity that erodes trust. When exits are necessary, clarity, compassion, and speed protect both people and culture.

Finally, I’ve adopted a brief reflection ritual that Alisa recommends every founder incorporate into their daily routine. Mine takes ten minutes at day’s end: What mattered most today? What did I learn? What will I do differently tomorrow? This lightweight cadence keeps me honest about progress, especially in the messy middle of the IC to manager transition and the broader journey from scrappy founder to established CEO. It’s also a lifesaver for leaders who struggle to give away their Legos.

You can follow Alisa on Twitter at @AlisaCohn.

Inspired by this post on First Round.

October 21, 2025
Inside Instacart’s Culture Playbook: Max Mullen’s Tactics for Values that Drive Behavior

Today, I sat down with Max Mullen, co-founder of Instacart, to dig into the craft of company culture with the precision it deserves. As a product leader, I’ve learned that culture is the operating system of the business—and Max’s journey from early generalist (running everything from product to payroll) to culture-focused executive offers a rare, tactical lens on how to build that OS with intent.
What struck me first was how deliberately he and the Instacart team approached company values. We unpacked the process behind defining distinctive principles—like “Every minute counts,”—and the mechanisms that ensure those values actually guide behavior. I shared how, on my own teams, we translate values into observable behaviors, interview rubrics, and operating rituals so they aren’t posters on a wall—they’re decisions in motion.
We then got practical about embedding values so employees truly feel connected to them. Max offered creative tactics that go beyond all-hands slides: narrative storytelling in onboarding, leader “value spotlights” in weekly reviews, and lightweight recognition loops that reward values-aligned choices. I added my playbook for hiring for values early on—using structured prompts, scenario-based assessments, and scorecards that map back to the behaviors we expect to see on day 30, 90, and 180.
From there, we dug into measuring culture—because what you don’t measure turns into mythology. We discussed using eNPS and pulse surveys, but also the importance of qualitative signals: skip-levels, anonymous async forms for hard feedback, and decision postmortems that reveal if incentives are aligned with stated values. I emphasized closing the loop publicly to build trust and make feedback feel consequential.
We also confronted the pitfalls that creep in as companies scale: easy-to-make founder mistakes, factions that emerge between early employees and newcomers, and the slow drift toward politics and bureaucracy. I shared a few guardrails I rely on: structured re-onboarding during hypergrowth, rotating “culture ambassadors” across functions, publishing decision logs for transparency, and codifying “how we decide” to reduce shadow politics.
The throughline is simple and powerful: founders and product leaders can and should take a deliberate role in shaping culture from day one. If you’re scaling now, run a quick audit: Are your values specific enough to create trade-offs? Do they appear in hiring, performance, and artifacts like PRDs and roadmaps? Can your newest team member explain how to live them in a tough decision? If not, you’ve found your next sprint.
You can follow Max on Twitter at @Max.
If you’re interested in learning more about how Cocoon makes employee leave easy, visit https://www.meetcocoon.com/

Inspired by this post on First Round.

October 21, 2025
From Good to Great: 3 Design Pillars, GTM Savvy, Hiring Loops, and Onboarding Rituals

I recently sat down with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment. As I reflected on the conversation through the lens of product management leadership, I saw clear patterns any design org can use to go from good to great. We dug into her three pillars of what makes a great designer: a product quality ambassador, serve as the glue across product areas, and intricately understand the go-to-market motion. I break down why each pillar matters, along with practical ways I’ve coached designers and PMs to build these capabilities without slowing momentum. First, being a product quality ambassador isn’t just about visual polish—it’s about product discovery rigor, clarity of problem definition, and crisp acceptance criteria that translate seamlessly into engineering execution. I look for designers who raise the bar in design reviews, connect craft to outcomes, and protect user experience end-to-end, not just at the surface layer. Second, serving as the glue across product areas is the multiplier. The best designers broker alignment among product, engineering, marketing, sales, and support. They see around corners, anticipate dependencies, and drive coherence across journeys. In practice, this shows up in cross-functional collaboration during product roadmapping and sprint planning, where designers orchestrate trade-offs to maintain a cohesive experience. Third, great designers intricately understand the go-to-market motion. When designers internalize how pricing, packaging, positioning, enablement, and adoption tie back to the product, they make higher-leverage decisions. I encourage teams to sit in on customer calls, shadow sales and support, and map product workflows to GTM milestones so the work lands with real users and real revenue. We also discussed hiring. She takes me through her hiring loop and how she probes for core competencies in each of these three areas. I’ve found structured work samples, system-thinking challenges, and a cross-functional collaboration exercise to be strong predictors. She also flags some of her own mistakes she’s learned from as a hiring manager—such as over-indexing on visual craft at the expense of product sense, or underweighting GTM empathy. My adjustments: calibrate rubrics to value problem framing and decision quality, not just artifacts; include partners from engineering and solutions in the loop; and debrief on signals tied to these pillars. On onboarding, her favorite rituals resonated with me. Pairing new designers with a solutions engineer accelerates context, builds credibility with customer-facing teams, and shortens the path to impact. Similarly, crowd-sourcing a “Dear New Designer” document captures tribal knowledge, expectations, and responsive norms in one living artifact—an elegant way to transmit culture and standards at scale. We then turned to leading a high-impact design org. She unpacks the aha moment that her fear of micromanaging had unintended consequences. I’ve seen this too—hands-off leadership can drift into ambiguity and uneven quality. The antidote is intentional structure: office hours for fast feedback, lightweight checkpoints for consistent quality, and team bonding events that reinforce shared taste and high standards. Done well, these rituals create autonomy with alignment—and a consistently elevated bar for design quality. To learn more about the “Dear New Designer” onboarding document, visit Hareem’s Medium page: https://medium.com/segment-design/dear-new-designer-1fd006fc7390 You can follow Hareem on Twitter at @hareemmannan.

October 21, 2025
Behind the Scenes of Canva’s Meteoric Rise: Zach Kitschke’s Battle-Tested Playbook

I’ve been reflecting on the story of Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation. As a product leader, that trajectory is a masterclass in product management leadership, product-market fit lessons, and deliberate go-to-market execution.

Zach was one of Canva’s first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead and spinning up the people function. That range resonates with my own experience in high-growth environments: early operators wear many hats to unblock the work and accelerate learning loops.

This career history gives Zach a unique vantage point on why Canva worked. I zero in on the early days — from unpacking all the work that went into their launch, to how they improved the early product and focused on the use case for social media managers and content creators. To me, the insight is simple and powerful: obsess over a clear initial ICP, deliver undeniable value for content creators, and let word-of-mouth amplify your early wins. That’s product discovery in action, supported by tight product roadmapping and sprint planning that prioritizes outcomes over output.

Next, I dig into supporting and scaling the team during hypergrowth. Canva has several unique practices around onboarding, learning and development, and keeping the team connected — from vision decks, strategy docs and a specific skills framework, to their ‘chaos to clarity’ spectrum and ‘season opener’ ritual for making company planning more fun. These practices make culture operational: they align teams on strategy, reduce ambiguity, and create repeatable rituals that sustain speed without burning people out.

From a leadership lens, I appreciate how these mechanisms turn tacit knowledge into shareable playbooks. Vision decks codify narrative; strategy docs create traceability; the skills framework clarifies expectations for IC to manager transition; and the ‘chaos to clarity’ spectrum gives product teams a shared language to navigate uncertainty. This is the scaffolding great product organizations rely on to scale quality, autonomy, and accountability.

Zach also shares what he figured out personally along the different chapters in his career at Canva, including how to leverage advisors and when to bring someone else in to take over your role. I’ve found those two moves to be force multipliers: advisors compress time to insight, and timely succession unlocks what the business needs next. Whether you’re a marketer, a founder, a people leader, or a product manager, there are tons of helpful takeaways for everyone here.

You can follow Zach on Twitter at @zachkitschke.

Inspired by this post on First Round.

October 21, 2025
Inside Hubspot’s Build: Co-Founder Compatibility, IC Leadership, and Engineering Culture as Product

I was energized by the depth and clarity in this conversation. Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. From my vantage point leading product at HighLevel, Inc., I zero in on what product leaders can operationalize right away: co-founder alignment, deliberate operating systems, and engineering-driven culture.

Early in the discussion, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. As someone who has built and led cross-functional product organizations, I appreciated the rigor behind this compatibility testing—clear expectations, explicit decision rights, and pre-agreed escalation paths. My takeaway for potential founding pairs: align on values and working agreements up front to increase the likelihood of success and smoother sailing.

What keeps Dharmesh engaged after all these years are foundational building blocks that make the role intrinsically rewarding. I loved his approach to eliciting feedback through “bug reports.” Treating leadership behaviors and team processes like software defects creates a safe, systematic way to surface issues fast. Equally compelling is his decision to never take on any direct reports and remain an individual contributor as a co-founder; IC leadership can be a force multiplier when the organization designs clear ownership boundaries and high-bandwidth interfaces.

The most striking arc in the conversation is how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product. As a product creator, I resonate with this framing: culture needs a roadmap, measurable outcomes, and tight feedback loops—exactly the mechanisms we use to build world-class products.

For product leaders and founders, the practical playbook is clear: test co-founder fit early and explicitly, invite “bug reports” to de-risk blind spots, design IC leadership paths alongside managerial tracks, and engineer culture with the same rigor you bring to the product. These patterns improve product-market fit internally—within your org—long before they amplify results in the market. That’s the compounding advantage I aim to cultivate every day.

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