In Depth

Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business Scho...

Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth. In today’s episo...

Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as...

Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox. –...

Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs. – In today’s episode, we discuss: Sam’s advice for future engineers What’s next for AI How to develop technical taste The importance of asking “what if” questions Les...

Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub. – In today’s episode, we discuss: What every marketplace founder should think about Why marketplaces a...

Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas. — In today’s episode, we...

Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. — In today’s episode, we discuss: Lessons on culture, org-design, and product from Rippling...

Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent. —  In today’s episode, we discuss: Lessons from Amazon, Microsoft, and Square “Minimum Remarkable...

Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple. — In today’s episode, we discuss: Why founders should...

Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage. — In today’s episode, we discuss: Why Eilon...

Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. — In today’s episode, we discuss: Lessons on culture and product from Amazo...

May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. —  In today’s episode, we discuss: Advice for AI f...

Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. — In today’s episode, we discuss: How AI is reshaping the softwa...

Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Manag...

Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. — I...

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. —...

Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. — In today’s episode, we discuss: Creating a community of power users How to stay ruthlessly...

Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. — In today’s episode, we...

Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is no...

Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned aut...

Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Wo...

Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to...

Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Pu...

Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. — In today’s episode we discuss:...