Lenny Rachitsky just launched Lenny’s Jobs, and honestly, this is the kind of thing I wish existed the last time I was looking for a job.
I realize it may seem a little odd to use Supra Insights to promote another jobs product. But I actually think they’re more useful together.
Lenny’s Jobs gives you a broad view of the market, with thousands of tech roles, roles shared directly through Lenny’s community, and the Lenny 100, his list of the 100 companies he would most want to join today. The AI pieces are super cool too. The site includes tools to help you evaluate roles and prepare for interviews.
Supra Insights will stay much smaller and more opinionated. I’ll keep looking through a larger set of openings and highlighting four or five that I find especially interesting at each level, with a heavier focus on senior product roles. Lenny’s Jobs is the broader market map, including many more opportunities for earlier-career and mid-career people.
The timing is kind of perfect because our latest Supra Insider episode is with Chris Lee, founder of Product Scout. We spent more than an hour watching Chris think through how a recruiter actually finds and evaluates product candidates, including live teardowns of Ben Erez’s LinkedIn profile and mine.
One of the main ideas we discussed is “candidate market fit.” Treat your job search like you’re building a product, except you’re also the product. Figure out the market you’re targeting, understand what that market values, position yourself clearly, and keep testing until you find where your experience really clicks.
So if I were searching for my next role today, this is how I’d put all of these resources together.
Before Chris gives someone feedback on their LinkedIn profile, he wants to know the lens. What stage of company are you targeting? What level? IC or management? Which domains or types of products make your background unusually relevant? Where can you realistically work?
It feels safer to keep all of those options open, especially when the market is competitive. The problem is that a profile written for a seed-stage startup, a Series C company, and Google at the same time usually gives a recruiter a lot of work to do. A recruiter should be able to understand what you’ve done and why this particular role makes sense for you without having to piece it together.
You can always change the target if it isn’t working. Chris’s advice is to think in multiple shots on goal. Pick one target segment, test it across a small group of relevant companies, learn from the response, and then adjust if you need to.
With a rough target in mind, explore pretty broadly. Start with the Lenny 100 if you keep defaulting to the same few frontier labs or companies you already know. Check the roles tagged “Lenny’s Community.” They come directly from the paid-subscriber Slack and Lenny’s monthly “Who’s hiring?” posts, which makes them a useful complement to the usual job boards.
I would pay attention to which requirements keep appearing, where your experience genuinely lines up, and which companies you actually want to learn more about. The repeated requirements tell you where demand is clustering. The response you get from recruiters and hiring teams tells you where the market sees value in your background.
Ben has a simple rule of thumb when he coaches candidates: focus most of your time on roles where you look like an 8 out of 10 fit. Once you find those, take them seriously.
The Fit Score inside Lenny’s Jobs can be one input. I would treat it as a prioritization tool, not a verdict. No score can fully capture adjacent experience, an unusual career path, or the advantage of a strong introduction. Supra Insights (this newsletter) can give you a much smaller shortlist of senior-leaning roles I personally find interesting.
I’ve seen very talented people underprepare because interviewing is one more thing on top of a full-time job. Then they run into equally strong candidates who spent much more time researching the company and working through their stories, and interviewers can tell during the loops.
In Chris’s process, LinkedIn is almost always the first screen, and he rarely starts with a resume. If the relevant experience isn’t visible on your profile, he won’t see it.
As the same requirements start appearing across your shortlist, go back to your profile. Make the relevant experience and results easy to find. Use the About section to connect the dots, especially if your path has a few turns in it. Under each role, Chris recommends two or three substantive bullets covering what you worked on, your role, and the outcome.
Keywords matter during sourcing because search tools, including Chris’s, use them to find and scan profiles. But the keyword still needs evidence behind it. Writing “AI PM” might help you appear in a search. Explaining what you built and what changed because of the work gives the recruiter a reason to continue.
Lenny’s interview toolkit brings together mock interview tools, courses, and some of the strongest free preparation resources I’ve seen in one place. It also features Insider Loops, which is a real honor for Ben and me. All eight of our company-specific PM interview guides are included, covering Anthropic, OpenAI, Google, Meta, Stripe, Figma, DoorDash, and Uber.
PM interview processes are changing quickly, so we treat every guide like a living product and keep updating it as we learn more.
A move to the right company can shape your learning, network, and compensation for years. That makes careful preparation worth the time.
If it’s a meaningful offer or the package is complicated, I would consider getting professional help before accepting it. Most people only get a real opportunity to reset their compensation every few years, and even a modest improvement to the base, bonus, or equity can add up over the time you stay.
The right expert can help you benchmark the offer, understand what may be flexible, and structure the conversation well. I would still ask how they are paid and whether they have experience with your level and the type of company you are joining.
Feel free to message me if you need recommendations for compensation-negotiation experts I’ve worked with. We’ve partnered with Valued for Insider Loops to help our customers with the negotiation process. We may earn a referral fee if you choose to work with them. I’m happy to make an introduction and see whether we can extend the same discount to you.
Whether or not you work with an expert, I recommend watching this video from Colin Lernell, the founder of Valued. I send it to everyone I know who is going through a compensation negotiation.
Huge congrats to Lenny and Amit Taylor for putting all of this together, and thank you for featuring Insider Loops so prominently in the interview toolkit. Seeing it at the top of the page means a lot to Ben and me.
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