Lenny's Podcast: Product | Career | Growth

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previous...

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

We discuss:

1. Why “extraordinary results demand extraordinary efforts”

2. Why you should deliberately understaff projects, and how to know when you’ve gone too far

3. Matt’s transition from COO to CPO and what surprised him about leading product

4. The “high alpha, low beta” framework for e...

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he...

Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new...

Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate—an AI agent designed to participate across the entire devel...

Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what’s good vs. what’s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped—the fastest company in history to reach this milestone. Before founding Surge, Edwin was a research scientist at Google, Facebook, and Twitter and studied mathemat...

Tomer Cohen is the longtime chief product officer at LinkedIn, where he’s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder program that teaches coding, design, and PM skills together. He’s also introduced a ...

Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy.

We discuss:

1. Why GTM is becoming more strategically important in the AI era

2. The rise of the GTM engineer

3. A prim...

Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coachi...

Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusi...

Dr. Fei-Fei Li is known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Google Cloud’s Chief AI Scientist, directed Stanford’s Artificial Intelligence Lab, and co-founded Stanford’s Institute for Human-Centered AI. In this conversation, Fei-Fei shares the rarely tol...

Grant Lee is the co-founder of Gamma, the AI-powered presentation tool that’s one of the hottest and most interesting AI startups in the world right now. They’re valued at over $2 billion, and they hit $100 million ARR in just over two years, with a lean team of just around 30 people. Unlike many fast-growing AI startups, Gamma has been profitable for most of its history, has not raised significant funding, and they built a massive...

Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on the skills founders need to learn to go from $1M to $10M ARR.

We discuss:

1. Why the “mid...

Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a techn...

Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO).

We discuss:

1. How Block’s internal open-source age...

Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has built multiple successful AI products and platforms and works directly with enterprises ...

Nicole Forsgren created the most widely used frameworks for measuring developer productivity—DORA and SPACE. She wrote the foundational book Accelerate and is about to release her newest book, Frictionless, a practical guide for helping teams move faster in the AI era. She’s currently Senior Director of Developer Intelligence at Google.

We discuss:

1. Why most productivity metrics are a lie

2. Signs that your engineering team could be...

Dylan Field is co-founder and CEO of Figma, a beloved tool used by every modern product team. Founded in 2012, Figma has expanded from a single design tool to a comprehensive platform including FigJam, Slides, Dev Mode, and, most recently, Figma Make. After a $20 billion acquisition by Adobe fell through due to regulatory pushback, Dylan led the company to a successful IPO in 2025.

What you’ll learn:

• How Dylan kept internal morale ...

Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions.

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What you’ll learn:

Why Google’s AI products are suddenly taking off after years of perceived stagnation 

How...