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 Characteristics of great CEOs How to a better executive leader Leading with kindness and impatience How to fight entropy — Referenced: Andy Roddick: https://www.atptour.com/en/players/andy-roddick ..read more

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 Products” versus Minimum Viable Products Navigating different work cultures in big tech Insider reactions to the disruptive launch of AWS “Pioneer” versus “fast-follower” companies —  Ref ..read more

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 build platforms, not apps The importance of “delighting” customers How Daffy is disrupting donor-advised-funds Lessons on strategy from LinkedIn How to think about leadership transitions — Reference ..read more

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 was so bullish on recording sales calls How Gong knew they had product market fit The importance of design partners Expanding into multi-product offerings Lessons from riding the AI wave since 2015 T ..read more

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 Amazon, Apple, and Microsoft Building and scaling DevTools Finding product market fit and monetizing it Why AI is complicating product market fit How Dennis prioritizes mental health as a founder The comm ..read more

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 founders in 2024 Why it’s difficult to scale AI products for enterprise The secret to finding champions Signs of a healthy co-founder relationship The future of agentic AI —  Referenced: A ..read more

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 software landscape Bridging the gap between ideas and software Why YC almost rejected Replit four times Replit’s fundraising difficulties, and how Paul Graham helped The secret lever Replit pulled to scale ..read more

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 Management at Opendoor. — In today’s episode, we discuss: Key product strategies used by Square and Gusto The pros and cons of building for SMBs How to build horizontal after creating a wedge The catch wi ..read more

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. — In this episode, we discuss: Common customer success mistakes Creating a world-class customer success org Tactics for hiring exceptional talent How to structure compensation packages Where customer su ..read more

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. — In today’s episode, we discuss: Lopp’s “utopia” — where engineers have time to create and invent What makes an excellent engineering leader The flexibility required for managerial roles in different ..read more