Lenny Rachitsky

Been playing with @ManusAI more and it's really really good. It's becoming me go-to for podcast guest prep.

My biggest learnings from Jeanne DeWitt Grosser (ex-Chief Business Officer at @Stripe, now @Vercel COO): 1. What failed seven years ago now works with AI. In 2017, Jeanne tried to build a system at Stripe that would automatically personalize outbound emails based on company data. Despite working with world-class data scientists, it failed due to too many errors. Today, that exact same approach works. This shows how AI has made previously impossible ideas suddenly viable. 2. A single GTM engineer at Vercel reduced a 10-person sales team to 1 (in just 6 weeks). Jeanne’s team at Vercel had an engineer build an AI agent that handles inbound lead qualification, outbound prospecting, and deal loss evaluation. The agent costs $1,000 per year to run versus over $1 million in salaries for the sales team. The nine displaced team members moved to higher-value work rather than being laid off, and the remaining salesperson is 10 times more efficient. 3. Their AI deal-loss bot has become better at understanding what went wrong than humans. When Jeanne analyzed her biggest loss of the quarter, the salesperson blamed pricing. But an AI agent reviewed every email, call transcript, and Slack message and discovered the real reason: they never spoke to the person who controls the budget, and when ROI came up, the customer clearly didn’t believe the value claims. They are now using AI to analyze sales calls in real time and send alerts like “You’re halfway through the sales process and haven’t talked to a budget decision-maker yet.” 4. Wait until $1 million in revenue before hiring your first salesperson. Founders should continue selling themselves until they reach around $1 million in annual revenue with a repeatable process. The key is having a defined ideal customer profile—customers who look alike. 5. Segment customers on what drives their buying decisions, not just company size. OpenAI has roughly 3,000 employees, which would typically put them in the “mid-market” category. But they’re a top-25 website globally by traffic, so Vercel treats them as enterprise customers requiring complex sales. Effective segmentation combines company size with growth rate, web traffic, workload type, and industry—because selling to e-commerce companies requires completely different language than selling to crypto companies. 6. Most customers buy to avoid risk, not to gain opportunity. About 80% of customers purchase to reduce pain or avoid problems, while only 20% buy to increase upside. This means you should focus your sales messaging on what could go wrong without your product—like falling behind competitors or damaging their reputation—rather than just talking about exciting features. This is especially true when selling to larger companies, where individual careers are on the line. 7. Sales teams should be indistinguishable from product managers—for a bit. Jeanne hires salespeople who have such deep product knowledge that if you put one in front of a group of engineers, it should take 10 minutes to realize they’re not a product manager. This credibility allows sales teams to serve as an extension of research and development—a 20-person sales team talks to hundreds of customers weekly and can translate those conversations into product insights at scale. 8. Building your own AI sales tools may beat buying off-the-shelf software. Because AI is so new and every company’s sales process is unique, Jeanne finds that building custom internal agents often delivers more value than buying vendor solutions. A single go-to-market engineer built their deal analysis bot in just two days, perfectly tailored to their specific workflow. These engineers shadow top salespeople to understand their workflows, then build automation that would have taken months or been impossible just a few years ago. 9. Make every sales interaction great, whether customers buy or not. Jeanne replaced boring discovery calls at Stripe with collaborative whiteboarding sessions where customers drew their payment architecture. Many customers had never visualized their own systems before. They left with a useful asset and a feeling of collaboration, regardless of whether they bought. Many returned years later to purchase. Think about your go-to-market process like a product, not just a sales function. 10. Product-led growth has a ceiling—no $100 billion company runs on it alone. While product-led growth (where users can sign up and start using a product without talking to sales) works well for early growth, customers generally won’t spend a million dollars through a self-service flow. Every major technology company eventually builds a sales team for larger deals. The mistake is waiting too long, since building a predictable sales process takes time.

This feels like a watershed moment. When the best engineers in the world are no longer writing a single line of code, and barely even looking at the code that's being generated. This would have sounded insane just a year ago. Hard to fathom what happens when the stuff @bcherny @steipete @karpathy are doing today becomes the norm for the rest of the software engineering field over the next few years.

AI makes it so much easier to build. But here's the catch: everyone else has that same speed advantage. So you turn to distribution. But here’s the second catch: the channels you’ve long relied on for growth (virality, sales, SEO, ads) are increasingly becoming less effective—for that same reason. So how do you get your product noticed? The answer is ecosystem. Instead of going directly to your prospects, go through intermediaries who already have access and trust with your audience. @TomOrbach , director of growth marketing at @wiz , said it best: “Why start at zero when you can start at 10,000?” - Gamma attributes over 50% of its growth to micro-influencers - Supabase 4x'd their growth in under a year thanks to a partnership with Lovable - Vercel grew off the back of its Next.js community - Lovable grew in large part by empowering creators to generate content about them - Clay grew through close partnerships with “GTM engineer” power users—consultants, agencies, and in-house operators In today's powerful guest post, @emilykramer shares how you can implement this strategy yourself, including dozens of real-world examples of how top AI companies like @Lovable , @GammaApp , @Clay , @Vercel , @Supabase , @TrustVanta , @basetenco , @HubSpot , and others are executing this strategy. Don't miss this one: https:// lennysnewsletter.com/p/ecosystem-is -the-next-big-growth …

AI tools with the most product-market fit We asked my 1m+ newsletter subscribers “Which AI tool(s) would you be very disappointed to lose access to?” ChatGPT dominates. Half of respondents (50.2%) would be very disappointed to lose ChatGPT. Claude came in second, followed by Cursor, Gemini, and then Claude Code. It's interesting to see @meetgranola at #7, and @Lovable right after.

"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR with @jjen_abel Jen is GM of Enterprise at @StateAffairsUS , co-founder @jjellyfish_co , and one of the sharpest minds I've ever met on all things enterprise sales. In this follow-up to our first chat two years ago (covering the founder-led sales zero to $1M phase), we focus on what founders need to know to grow from $1M to $10M ARR. We discuss: The dangers of pricing your product $10K-$20K Why tier-1 logos counterintuitively make the best early customers Why the “mid-market” doesn’t exist How to find and work with design partners Why you need to vision-cast instead of problem-solve Why services are the fastest way to get your foot in the door with enterprises When to hire your first salesperson and what profile to look for Much more Listen now • YouTube: https:// youtube.com/watch?v=37fKFW drMyA … • Spotify: https:// open.spotify.com/episode/29WRTO clMiqAILT077dPe5 … • Apple: https:// podcasts.apple.com/us/podcast/sel l-the-alpha-not-the-feature-the-enterprise/id1627920305?i=1000735957465 … Thank you to our wonderful sponsors for supporting the podcast: @WorkOS —Modern identity platform for B2B SaaS, free up to 1 million MAUs: https:// workos.com/lenny @Lovable —Build apps by simply chatting with AI: https:// lovable.dev @coda_hq —The all-in-one collaborative workspace: https:// coda.io/lenny