Marc Baselga

In April, we’re hosting in-person events for product leaders in NYC, Oakland, Boston & Seattle. These events are intentionally small (8–14 attendees), and we only have a couple of spots available for non-Supra members — so apologies in advance if we’re not able to accommodate everyone. If you’re interested, check out the links below 🪩 04/22 – Supra NYC Meet-up: buff.ly/tF10960 🪩 04/23 – Supra Oakland Meet-up: buff.ly/phjt8CU 🪩 04/30 – Supra Boston Meet-up: buff.ly/WAJnteF 🪩 04/30 – Supra Seattle Meet-up: buff.ly/pUfKLfG

A product leader at Adobe with zero coding experience just showed me his AI chief of staff. It's a folder of markdown files on his Mac. Michael Leibovich runs product, design, support, and business strategy across multiple teams. His normal system for staying organized broke under the weight. Too many meetings, too much context switching. So he set up Claude Code to help him think. No GitHub. No terminal. Just Claude pointed at a set of text files. Inside that folder is a personal wiki with his role, teams, and strategic priorities. The decision frameworks he actually uses. And clear rules for what Claude can read, write, and update. He started by asking Claude to generate a set of extraction questions, then fed those to ChatGPT, which had years of memory about him. ChatGPT produced a 3-page markdown file as his starting context. 10 minutes. And the outputs were immediately better. Now the system briefs him before every meeting with context on attendees and open threads. End of day, it processes all his meeting notes and surfaces what actually needs his attention. It even auto-updates a people file from transcripts. When someone on his team mentions they're going on parental leave, the system reminds him weeks later to plan the project transitions. Between meetings he keeps asking the same thing. What's the highest leverage thing I should focus on right now? Instead of burning 30-minute windows triaging Slack, he gets a real answer. One that knows his calendar, his priorities, and what's blocking other people. He built this during paternity leave and described it as "daunting but not hard." The full walkthrough is on this week's Supra Insider. Folder structure, scheduled tasks, MCP integrations. Everything you'd need to build your own. Here's the link to the episode: buff.ly/8BOS4nv

If I was a PM in the market right now, @AnthropicAI would probably be my top choice. @gokulr has a fantastic framework for picking companies. It comes down to trajectory, talent density, and culture. Anthropic checks all three right now. (1) Trajectory - They went from $1B to $30B ARR in 15 months. 10x year-over-year. Their head of growth Amol Avasare just shared on @lennysan's Podcast that they’re actively hiring PMs because engineers with Claude Code are shipping so much faster that PM teams are stretched to keep up. - When a company is growing this fast, the pie expands. More responsibility, harder problems, nobody fighting over scraps. (2) Talent density - Amol described it as “playing for Real Madrid” (as a Barcelona fan, this was a tough one to hear). Mike Krieger started Instagram and he’s there. - These are the people who’ll pull you into your next 3 roles. Future co-founders, investors, people you can recruit into your startup someday. You get to see what great looks like up close. (3) Culture - Amol said he’s never met a single person at Anthropic who’s not putting everything they have on the table. They have these notebook channels on Slack, basically internal Twitter feeds where anyone can publicly disagree with Dario. A new hire challenged something he said at an all-hands and it sparked a company-wide debate. - They’re also comfortable leaving money on the table for safety. That’s not something you hear from a growth team. What they’re doing (and their product velocity) is impressive AF and the way they’re working is just as fascinating as what they’re shipping. If I was applying, I wouldn’t leave the process to chance. I’d try to get as much alpha as possible. There’s barely anything out there about how Anthropic interviews PMs, which is why I'm excited to share we launched our newest Insider Loops guide covering their interview loop! insiderloops.com

Anthropic went from $1B to $19B ARR in 14 months and they're strapped for strong PMs. Anthropic has been our most requested guide at Insider Loops and their head of growth Amol Avasare just shared on Lenny's Podcast that PM teams across the company are stretched and Anthropic is actively hiring strong PMs. If you're thinking about joining Anthropic, this is a great time to get in the door. The timing of this episode couldn't be better because today we're announcing the launch of our Anthropic guide. This is our 7th Insider Loops guide, following OpenAI, Google, Stripe, DoorDash, Figma, and Uber. To create this guide, we spoke off the record with PMs at Anthropic and candidates who recently went through their interview process to unpack each step of the loop and what's being evaluated. Out of all the guides we've created, it feels like Anthropic takes culture interviews more seriously than any other company. They're looking for PMs they can trust with the heavy responsibility of bringing AGI to the world. Ben Erez joked when we were putting the final touches on the guide that it seems like they're screening for PMs who can see the Black Mirror episode downstream of every decision and pick the other path. There's barely anything out there about Anthropic's PM interviews online, so we had to dig deep on this one. ↳ How the loop is structured and what each stage actually tests ↳ How their obsession with safety shows up in how they evaluate candidates ↳ The failure patterns that get candidates eliminated ↳ How to prep for a company where most of your old playbook won't apply I'm sure the loop will evolve, and we'll keep updating as new insights come in from real candidates. Check it out at insiderloops(dot)com

One of the most common mistakes I see with leaders, especially newer ones joining a new company, is they over-adapt to the environment. And I get why. You want to learn the norms, understand how things work, build trust before you start changing things. That part matters. But there's a difference between learning the environment and disappearing into it. Hiten Shah, Ben and I got into this on our latest Supra Insider. Leaders end up shaping how their team works, whether they realize it or not. That's not a bad thing, it's just how it works. The only question is whether you're doing it consciously. When it's not conscious, people are just guessing. They're reading your signals through the lens of whatever leader came before you, and same words can mean completely different things depending on who said them before. Nobody tells you this is happening and they just quietly adapt to what they think you want. Hiten saw this play out firsthand. His boss Morgan Brown joined the company and was smart about this from day one. He came in with an operating manual about himself. How he thinks, what he values, how he communicates. Hiten literally walked around handing it to people. Even then, some people misread Morgan's intentions. Not because Morgan was unclear, but because they were filtering him through the previous exec's style. At one point a team member read something Morgan wrote in Slack as critical and came to Hiten for help. Morgan didn't mean it that way at all. Old patterns just die hard, and Hiten found himself translating between Morgan and the team. If you don't define how you operate, your team will invent it for you. And they'll base it on whoever came before you, not on you.

Anthropic went from $1B to $19B ARR in 14 months and they're strapped for strong PMs. Anthropic has been our most requested guide at Insider Loops and their head of growth Amol Avasare just shared on @lennysan's Podcast that PM teams across the company are stretched and Anthropic is actively hiring strong PMs. If you're thinking about joining @AnthropicAI , this is a great time to get in the door. The timing of this episode couldn't be better because today we're announcing the launch of our Anthropic guide. This is our 7th Insider Loops guide, following OpenAI, Google, Stripe, DoorDash, Figma, and Uber. To create this guide, we spoke off the record with PMs at Anthropic and candidates who recently went through their interview process to unpack each step of the loop and what's being evaluated. Out of all the guides we've created, it feels like Anthropic takes culture interviews more seriously than any other company. They're looking for PMs they can trust with the heavy responsibility of bringing AGI to the world. I joked to @MarcBaselga when we were putting the final touches on the guide that it seems they're screening for PMs who can see the Black Mirror episode downstream of every decision and pick the *other* path. After getting dozens of pings in recent months about how little information is available about Anthropic's PM interviews online, our guide is now the best resource for candidates to understand their interview process. I'm sure the Anthropic loop will evolve quite a bit in the coming months and thanks to our steady flow of insights from real candidate, we'll update our guides on a weekly/monthly basis as new changes are rolled out. You can get the guide here: insiderloops.com And a quick personal note: if I was looking for a PM role, Anthropic would probably be my top choice right now. What they're doing is impressive AF and the way they're working is just as fascinating as what they're shipping.

Two questions are getting mixed up in many product orgs right now, and they have very different answers. 1. Should PMs have access to agentic coding tools that have read access to the company's codebase? 2. Should PMs push code to production? IMO, the first one is an easy "yes". Every PM should have access to Claude Code, Cursor, whatever your team uses. The prototyping benefits alone are worth it. Requirement reviews are turning into prototype reviews. PMs are showing working artifacts instead of static specs. And questions that used to require pulling in an engineer, things like "what does this integration actually do?" or "how do we handle token expiration?", you just ask the codebase directly. The second one is where it gets complicated. The strongest pushback I'm hearing from engineers comes down to one question. If you won't feel confident fixing something you ship that breaks production, you probably shouldn't be shipping it. Chase Schwalbach SVP of Product and tech at Millie broke this into two buckets on a recent Supra Insider episode. 1/ Small changes from anyone are fine. Big features stay in the sandbox. Content updates, UI tweaks, with engineering review, sure; ship them. But big features from someone without deep engineering context, stay in prototype mode. Demo it, get buy-in, hand it off to eng. AI can take you down some wild architectural paths if you don't know what to watch for. 2/ The review gate stays the same regardless of who writes the code. Someone who understands scalability and architecture reviews before anything ships. Break up large PRs so reviewers can follow the logic. Write more tests, AI makes this trivial now. The accountability bar doesn't drop just because authorship changed.

The wrong environment turns your best people into spectators. Hiten Shah sold his company to Dropbox and became an IC for the first time in his career. On our latest Supra Insider, he talked about what that shift taught him. He'd spent his whole career shaping the environment. Now he was inside one he didn't build, and that gave him a perspective most founders never get. From that vantage point, he saw how leaders watch output slow down and assume the person wasn't as good as they thought. So they add more process, more oversight. Slow suffocation disguised as management. The talent didn't change. The problem is that the leader misdiagnosed an "environment problem" as a "talent problem". Hiten thinks we obsess over "culture fit" when culture is mostly emergent behavior. What leaders actually control is the environment. And that starts with how they operate, what they reward, and how they make people feel. So he stopped interviewing for culture fit and started testing for environment fit. His company ran on "measure twice, cut once." Nobody writes production code without 90%+ confidence in the plan. So his hiring process tested for exactly that. Candidates got a two-page brief and had to explain how they'd build it. No code. Just the plan. Then they spent 90 minutes with the hiring manager, who had already scored the plan in advance. Most of the conversation was simulated feedback, as if the candidate were already in the role. Great engineers who like to move fast and figure things out while shipping would never pass. They'd be miserable there, and the team would be frustrated, too. This is a good reminder for leaders: Before you decide someone isn't good enough, ask whether the environment made their edge unusable. 🎙️ Links to the full episode coming soon!

Series B is where Heads of Product realize their old playbook stops working. I keep hearing the same thing from HoPs in Supra: "I muscled us into PMF. Now I am not sure what my job is anymore." At Series A you: ↳ sit in on most customer calls ↳ decide what ships next ↳ jump into specs and tickets when things stall That got you the Series B. Then headcount jumps, you have multiple PMs and a real GTM org, and those same habits quietly turn you into the bottleneck. The best Series A HoP can become the worst Series B HoP by doing exactly what made them successful before. The same three shifts keep coming up: 1/ Heroics → systems Stop being the approval bottleneck. Start creating simple rules for what gets built and why. Your leverage shifts from "have the right answer in every meeting" to "design the way this org makes decisions". 2/ Owning the roadmap → owning the product org At 30 people you can fix confusion in a hallway conversation. At 150 people across multiple teams, confusion becomes the default. So more of your attention goes to things like: ↳ clear scopes and metrics by PM ↳ clean interfaces between PM, design, eng, data and GTM ↳ the minimum structure you need so work does not get re-litigated in every meeting Your real product at this stage is the operating system of your product org. If that system is clunky, everything you ship will feel clunky too. 3/ Doing the work → scaling yourself You got here because you were an excellent IC. Series B tests whether you can make other people excellent. That looks like: ↳ hiring PMs who can own outcomes, not just backlogs ↳ coaching them on narrative, tradeoffs and stakeholder management instead of rewriting every doc ↳ being explicit about when you step in and when you let them make the call It feels slower at first. But if you keep jumping in to fix everything yourself, you train the org to depend on you forever. There is no neat job description for "Head of Product at Series B". You are part IC, part org designer, part translator between founder, board and team. It is a lot. Inside Supra we are spinning up a small Series B Heads of Product group: ↳ 7 to 8 top product leaders at roughly Series B stage ↳ monthly 90 minute sessions where you bring real docs, decks and decisions, not hypotheticals We will dig into things like: ↳ designing your product org and hiring plan for the next 12 to 18 months ↳ saying "no" to founders and sales without losing trust ↳ building a coaching system so PMs develop their own judgment Not group therapy. Not generic networking. Heads of Product helping Heads of Product scale themselves and their orgs through Series B. Application: buff.ly/A0mmA0B Hard requirement: You must be currently a HoP/VP of product at a Series B-C company.

Ben Erez's first advisory engagement taught him something I now see often in our Supra community: A lot of advisory relationships don't work out because nobody explicitly defined what the relationship was supposed to look like between sessions. Back to Ben's story: He and the founder were operating under two completely different models of "advisory," and neither of them surfaced the difference early enough. The founder expected what Ben now calls a "push model," where the advisor proactively thinks about your problems, messages ideas, goes to bat for you on their own time. Ben was operating as a "pull model," where you bring the problem and he goes deep with you in the moment, but beyond that, there's zero expectation. Neither was wrong, but the gap showed up fast. Within a few weeks, both sides felt it; neither had the language to name what was off, and the engagement fell apart. Ben went on to run several really successful advisories after that though, all using the pull model. Same person, same skills. The only thing that changed was being explicit about the model upfront. He breaks all of this down in a masterclass on fractional work we recently posted as a Supra Insider episode. This same dynamic shows up everywhere, not just advisory work. Coaching, consulting, fractional leadership, even some board relationships. Anytime two people have assumptions about what happens outside of their scheduled time together. One question would've saved Ben's first engagement: "What does this look like between sessions?" Episode to Ben's masterclass coming soon.

We know a PM who took a full week of PTO to prepare for their Stripe interviews after buying our Insider Loops guide. They doubled down on prep time specifically because our guide highlighted that successful candidates self-reported spending 40+ hours preparing for the loop. Since Stripe was the PM’s dream company, they told themselves, “if 40 hours is what it takes, 40 hours is what I’ll invest.” This story is exactly why we’re excited to build Insider Loops. Stripe's PM interview is long and technically demanding, but the evaluation criteria are consistent and specific. If you know what each round actually tests and where people typically get tripped up, you can prepare very differently from people who don't have this information. Our guide covers every stage of the process, broken down by what's being evaluated and how. Written exercise strategy. Technical interview prep. Committee mechanics. All from direct conversations with insiders and candidates who have recently gone through the interviews. Grateful to play a small role alongside Ben Erez in helping people land dream roles with life-changing compensation. If curious about what we're building, check us out at insiderloops(dot).com

Searching for your next product leadership role but not sure where to look? Every two weeks, I'll be posting a curated list of open Product Leadership Roles at leading companies to help people who are actively looking for jobs. For context: I run Supra, a private community of high-caliber product leaders, so I have access to roles our community members are hiring for and jobs posted in our job-openings Slack channel. Here are the most interesting roles: Prefer to get the the roles via email 📧? Subscribe to this bi-weekly job listing here: buff.ly/DTjIevC. 𝐇𝐞𝐚𝐝 / 𝐕𝐏 𝐨𝐟 𝐏𝐫𝐨𝐝𝐮𝐜𝐭 𝐫𝐨𝐥𝐞𝐬 - Pathos is hiring a Head of Product - Interested? Reply directly to our newsletter email with a blurb explaining why you think you're a great fit. - Bounce is hiring a Head of Product - buff.ly/gH6C3O1 - Certara is hiring a Vice President of Product Management - buff.ly/nFsFht8 - PayPal is hiring a Vice President of Product – Identity - buff.ly/xqsZdDT - Twitch is hiring a VP of Product, Commerce - buff.ly/MtqS7Yj - Roblox is hiring a Head of Product, User Growth - buff.ly/l4Iwng6 - Polymarket is hiring a VP of Product - buff.ly/qJrUjrA 𝐃𝐢𝐫𝐞𝐜𝐭𝐨𝐫/ 𝐒𝐫 𝐃𝐢𝐫𝐞𝐜𝐭𝐨𝐫 𝐨𝐟 𝐏𝐫𝐨𝐝𝐮𝐜𝐭 - Google is hiring a Director, Product Management, Wearable Software - buff.ly/3WSVYpo - Blue Origin is hiring a Director, Product Management, Technical - buff.ly/88DhVyE - Adobe is hiring a Director of Product Management, Engagement & Monetization - buff.ly/2vp0IGl - Salesforce is hiring a Product Management Director, Data 360 - Data Foundations - buff.ly/ynURcVt - NVIDIA is hiring a Director, Product Platform Retail and CPG Industries - buff.ly/io84P7K - Okta is hiring a Director, Product Management - Okta for AI Agents - buff.ly/TamGL9I - The Trade Desk is hiring a Director, Product Management – Developer Experience & Platform - buff.ly/caRfRkc - Reddit is hiring a Senior Director of Product, Ads Platform - buff.ly/vJtAka1 - PrizePicks is hiring a Director of Core Products - buff.ly/3V55VZt 𝐆𝐫𝐨𝐮𝐩 𝐏𝐌 / 𝐏𝐫𝐨𝐝𝐮𝐜𝐭 𝐋𝐞𝐚𝐝 - Google is hiring a Group Product Manager, Performance Rewards and Global Mobility - buff.ly/XY6EcXA - BambooHR is hiring a Group Product Manager - Liability Services & Treasury Services - buff.ly/P1ZUywa - HubSpot is hiring a Group Product Manager, Data Platform & Context - buff.ly/IFxkHgd - Rippling is hiring a Product Lead, AI Platform - buff.ly/PrqJ7tJ - Vanta is hiring a Group Product Manager, GRC Workflows - buff.ly/UZrISM9 - Uber is hiring a Group Product Manager, AV Labs - uber.com/global/en/care… - Uber is hiring a Group Product Manager, Fares platform - uber.com/global/en/care… 𝐏𝐫𝐢𝐧𝐜𝐢𝐩𝐚𝐥 / 𝐋𝐞𝐚𝐝 𝐏𝐌 - GitHub is hiring a Principal Product Manager, Agent Platform - github.careers/careers-home/j… - Pinterest is hiring a Staff Product Manager, AI Safety - pinterestcareers.com/jobs/7718015/s… - BetterUp is hiring a Staff Product Manager - buff.ly/TxM6SGX - Snap Inc is hiring a Staff Product Manager, Ads Product - App Ads - buff.ly/hP3HUTh - Google DeepMind is hiring a Staff AI Product Designer, Gemini Assistant, GeminiApp - job-boards.greenhouse.io/deepmind/jobs/… - Cloudflare is hiring a Senior/Principal Product Manager - Durable Objects - job-boards.greenhouse.io/cloudflare/job… 𝐓𝐨 𝐬𝐞𝐞 𝐦𝐨𝐫𝐞 𝐫𝐨𝐥𝐞𝐬, 𝐜𝐡𝐞𝐜𝐤 𝐨𝐮𝐭 𝐨𝐮𝐫 𝐒𝐮𝐩𝐫𝐚 𝐣𝐨𝐛𝐬 portal 𝐰𝐢𝐭𝐡 +80 𝐨𝐩𝐞𝐧 𝐫𝐨𝐥𝐞𝐬 > @supra/supra-job-board" target="_blank" rel="nofollow noopener">coda.io/@supra/supra-j… If you know someone looking for a job or hiring, tag them in the comments or repost this post to help spread the word. Follow me (Marc Baselga) to receive these job openings.

Being a startup's first PM hire is not easy. You're the first product person. No process, no roadmap, no team. Just you and a founder who's been making every product decision since day one. A few founding PM challenges I've seen come up over and over: 1/ Can you shift from helper to owner? When you're the first PM, everything feels like your job. QA, support tickets, SQL queries, marketing copy. Some of that is unavoidable. But if you stay there too long, you train the founder to see you as execution support, not product leadership. ↳ pick 2-3 things that are uniquely PM work and start spending more time there ↳ build lightweight processes so the gaps you fill can be filled by someone else 2/ Can you build a system, not just execute inside chaos? Engineers were already shipping before you arrived. The founder was already making calls. So the question hanging over your role is simple: what changed because you joined? You ship. And ship. And ship. But if all you do is execute, you're a fast task-doer, not a product leader. The things that actually compound, like how decisions get made and how you learn from customers, are the things nobody is asking you to build. Ship fast in the first 90 days. But carve out time for infrastructure that compounds. 3/ Can you earn trust with the founder? The founder has been the PM since day one. Handing product decisions to someone they just hired is hard. At first, they still own most of the real product calls. That's normal. The way you flip that ratio isn't dramatic. Small wins. Demonstrated judgment. Knowing the customer better than anyone. Bring customer evidence, not opinions. 4/ Can you make your growth path explicit before someone else gets hired above you? This might be the biggest career risk of the founding PM role. The implicit deal is: do great work, and you'll grow into the leadership role. But that deal is rarely made explicit. And if you just keep your head down, there's a real chance someone more experienced gets hired above you. I've seen this inside Supra. The founding PM builds the product function from zero, does the unglamorous work nobody else wanted. Then the company raises and hires a "real" Head of Product from a bigger company. Have the conversation early. Not "promote me" but "what does growth look like for me here?" If the answer is vague, that's information too. If any of this feels familiar, we're spinning up a small founding PM group inside Supra. 7-8 founding PMs at seed and early-stage startups. Monthly 90-minute sessions. Real situations, not hypotheticals. Application here: buff.ly/UadKiT6 Hard requirement: you must be a current founding PM or first PM hire at an early-stage startup.

Supra is hosting in-person events for product leaders in SF, NYC, & Seattle. These events are intentionally small (8–14 attendees), and we only have a couple of spots available for non-Supra members — so apologies in advance if we’re not able to accommodate everyone. If you’re interested, check out the links below: 🪩 03/31 – Supra SF Meetup: buff.ly/HAVBh8p 🪩 04/30 – Supra NYC Meetup: buff.ly/inyXlY2 🪩 04/30 – Supra Seattle Meetup: buff.ly/wSOci8d

Curious about what top Product Leaders are reading right now? Here are 5 of the sharpest pieces shared in Supra this month: 1/ How Will OpenAI Compete? by Benedict Evans Evans makes the case that OpenAI doesn't have a durable moat yet. Frontier models are converging, engagement is a mile wide but an inch deep, and incumbents have stronger distribution. Massive capex might buy a seat at the infrastructure table, but not platform power. Can they build network effects before foundation models become commodities? buff.ly/O9XARkE 2/ The "traditional CPO" Role Will Vanish by Gokul Rajaram Gokul predicts the CPO role will disappear in five years as AI-native companies merge Product, Design, and Engineering into a single "product builder" archetype. For early and mid-career leaders, his advice is to stop aspiring to CPO and start building skills across all three disciplines. A provocative read no matter where you land on it. buff.ly/C5jIWAx 3/ AI Makes You Boring This post argues AI is flattening originality, not just accelerating development. "Vibe-coded" projects feel shallow not because tools got better, but because thinking got offloaded. Original ideas come from immersion, from wrestling with a problem and articulating it yourself. If you're building with AI and wondering why everything starts to look the same, this is a good gut check. buff.ly/wAamssF 4/ Welcome to the Room by Jeffrey Snover Satya Nadella's architecture for leadership distilled into a few sharp principles. Your job is manufacturing success with allocated resources, not complaining about constraints. The only way to survive is allocating resources ahead of conventional wisdom while staying intellectually honest about your theory of success. Not a long read, but every sentence hits. buff.ly/qc40Pz1 5/ How to Fix Your Entire Life in 1 Day by Dan Koe A long-form essay on why most change efforts fail and how identity, fear, and unconscious goals keep us stuck. Not light reading, but worth bookmarking if you're craving a real pattern break rather than another productivity hack. buff.ly/MRALczn What other great content did you read this month?

Fractional work sounds freeing until you realize your real job is selling yourself. The benefits are real. Time flexibility, exciting projects, diversified income. But what catches most PMs off guard is you have to do something they've never done: marketing and selling. No company brand behind you and nobody handing you leads. Ben Erez has spent two years doing fractional work full-time, testing different models, killing the ones that didn't work, and paying close attention to where demand actually pulled. He recently put out a masterclass breaking down what he learned. Three ideas from it that I keep coming back to: 1/ You are the product (so treat this like PMF discovery) When you go fractional, you're running product-market fit experiments on yourself. And like any good zero-to-one process, most will fail. Ben's path makes the point. He tried a product design studio and killed it when the budgets weren't there. Tried juggling two part-time PM roles and realized it wasn't sustainable. Some things failed because the model was wrong. Some failed because the company ran out of money. A few things stuck: the podcast, a reworked Maven course, Insider Loops and an AI copilot that generates revenue on its own. PMs understand this discipline for products. Very few apply it to their own careers. 2/ Narrow your positioning (even when it feels wrong) Your instinct is to keep things broad. "I can do strategy, zero-to-one, growth, analytics, whatever you need." Feels smart. But founders always have a specific problem and want the perfect person for it. When you say you can do everything, they assume you're not the best at their thing. Phil Carter is a good example. He carved out growth advisory for seed-to-Series-C consumer subscription companies. That specificity is why he gets pulled into the right conversations. Ben calls the opposite a "failure state." If someone in your network hears about a problem you could solve and doesn't think of you, that's on you. 3/ Don't fall into the feast or famine trap You land a big engagement and go heads down to crush it. You want a great testimonial, maybe referrals. So you go into what Ben calls "the impact cave." While you're in the cave, your pipeline dies. No marketing, no content, no coffee chats. When that engagement ends (and they always end), you're scrambling from zero. Ben saw this constantly at Continuum, a marketplace for fractional executives. The people who did best kept 10-20% of their time for marketing and demand generation, even when busy delivering. Fractional work is not just product leadership without a full-time employer. It's a business. The people who do it well position clearly, test fast, and keep generating demand while they deliver. Ben's masterclass is worth checking out if you're serious about this path. Link to full masterclass coming soon!

We’re hosting in-person events for product leaders in SF, NYC, & Seattle. These events are intentionally small (8–14 attendees), and we only have a couple of spots available for non-Supra members — so apologies in advance if we’re not able to accommodate everyone. If you’re interested, check out the links below: 🪩 03/31 – Supra SF Meetup: buff.ly/HAVBh8p 🪩 04/30 – Supra NYC Meetup: buff.ly/inyXlY2 🪩 04/30 – Supra Seattle Meetup: buff.ly/wSOci8d

If you rely on intel about Stripe's PM interview process from six months ago, it's still directionally right but 20-30% misleading. And it's not just Stripe. That's what makes Insider Loops hard to replicate. The guides themselves are already difficult to get right - Ben and I have spent years building trust with candidates, recruiters, and people inside these companies. And Ben Erez is a PM interview expert. But the part I think is even harder to replicate is what happens after a guide ships. We've built enough trust over time that people proactively come to us when something changes. We don't chase it down. And honestly, a lot of times we end up learning about process changes before people inside these companies do, just from the sheer number of candidates we talk to. Here's what changed in our Stripe guide in a single update cycle: ↳Product Sense question bank went from candidate reports to recruiter-confirmed ↳We identified the specific question with the highest failure rate in the PS screen ↳ The written exercise used to be a separate step. Now it gets sent at the same time as the onsite invitation and runs in parallel. ↳A candidate was called out mid-interview for saying "we" too often. Stripe wants to hear what you did, not your team. ↳Analytical interview expanded with 13+ new questions we hadn't tracked before And this is just an example of one cycle for one guide. We do this across six companies. Those frequent updates and "guide freshness" are really what you're buying when you get a guide from us. Not a static document that ages out, but something that stays current because people keep feeding us what's changing. P.S. Full Stripe playbook (with ongoing updates) at insiderloops(dot)com.

So back in the 1970s there was this Japanese soldier discovered on a Philippine island, still convinced World War II was going on. Nearly 30 years after the war ended, Hiroo Onoda was still in the jungle keeping his rifle clean. He only surrendered when his former commanding officer came and formally relieved him of duty. Jerry Colonna shared this story during a session we hosted inside Supra. He calls the concept the loyal soldier. It's the survival strategy that once protected you and never got turned off. For product leaders, this looks like the inability to say no even when your plate is literally breaking, the heroic late nights that everyone praises but nobody questions, or taking on the emotional weight of your entire team, your product, your company. These patterns protected you. They may have also been rewarded for years. But they're still running, and the war is long over. When Onoda finally came home, people didn't mock him for fighting a war that had ended decades earlier. He was welcomed back, and over time the weapon was gently taken out of his hands. Jerry says the same thing applies to our own patterns. Most of us try to fight our inner critic by yelling at it. Shut up, stop telling me I'm not good enough. It just gets louder. What actually works is you acknowledge it. "You're just trying to protect me, but I got this. I'm not eight years old anymore." Next time you catch yourself saying yes to something you know you should decline, or staying late because leaving feels wrong, ask yourself whether that's actually necessary or whether it's the loyal soldier. Jerry says he asks his Exec clients that question all the time, and 80% of the time it's not. I've been asking myself which of my own habits are loyal soldiers that never got the memo.

Many product leaders I'm talking to right now are asking the same question: "How do we measure AI adoption?" Leadership is pushing "do AI" mandates. Teams are scrambling to prove they're doing it. And almost everyone is measuring the tool, not the outcome. This came up in a recent discussion in our Supra Slack. Some teams are counting tokens. Literally measuring how much people use a platform as the metric. Others post slides at all-hands showing connector usage. "40 unique people used the Notion connector this week." One Head of Product vibecoded a spinner wheel with all PMs' names on it. If your name comes up at the weekly meeting, you demo something you built with AI. (I actually love this one.) These are creative. Some are even useful for culture. But none of them tell you whether the work is actually improving. One leader I spoke with skipped usage tracking entirely and took a different approach. ↳ survey her team for their biggest pain points ↳ pick 2-3 that AI could actually solve ↳ set specific measures for those problems Instead of "are people using AI?" she was asking "what's getting better?" And once you frame it that way, the metrics become obvious. ↳ Time to first draft ↳ PRD turnaround time ↳ Customer research synthesis time ↳ Hours saved on recurring workflows Those tell you whether AI is improving the work, not whether people opened the tool.