In Depth

David Lieb, Director of Google Photos and former CEO of Bump, shares insights on scaling a product to over a billion users. He discusses the evolution from Bump to Google Photos, emphasizing the importance of targeted user feedback and team dynamics. David reflects on past mistakes, corporate challenges, and the need for clarity in product vision. He also highlights how Google Photos transformed from mere storage to a tool for reliving memories, providing valuable lessons for aspiring product builders.

Bill Carr and Colin Bryar, former Amazon executives, share insights on Amazon's culture of innovation, including the origin stories of the Kindle, AWS, and Prime businesses. They discuss the importance of full-time focus on innovation, customer obsession, diving deep, and developing controllable input metrics. They also explore the significance of balancing customer interests, transparent policies, and Amazon's structured interviewing process.

Anne Raimondi, Chief Customer Officer at Guru and board member at companies like Asana and Patreon, shares her extensive leadership experience. She reveals key traits that successful executives possess, such as adaptability and humility. Anne emphasizes the importance of a structured 30, 60, and 90-day plan for new executives to build trust and engage their teams. She also discusses effective executive recruiting strategies and the significance of inclusivity in board dynamics, providing invaluable insights for current and aspiring leaders.

Jean-Denis Grèze, Head of Engineering at Plaid and former Director of Engineering at Dropbox, shares insights on leadership, pragmatism over perfection, team motivation, KPI tracking, and fostering ownership mentality in engineering. He emphasizes prioritizing technical debt, aligning team performance with business goals, and hiring strategies for engineering roles. A must-listen for technical leaders looking for actionable advice.

Dave Girouard, CEO and co-founder of Upstart and former President of Google Enterprise, shares insights on starting and growing Upstart, the challenges of fundraising, the successful pivot, and his management philosophies. He emphasizes the importance of believing in the product, shares helpful frameworks for startup leaders, and discusses managing the executive team.

Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello. In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity. In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup. This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/  You can follow Jay on Twitter at @jaysimons. You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort.  After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways.  She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart. Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone. You can follow Cristina on Twitter at @cjc. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.   You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom”  For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg.  To learn more about how Drift approaches storytelling, check out this article David wrote for Inc: https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html  To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/ You can email us questions directly at review@firstround.com or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson) 

Our third episode is with Steve El-Hage, co-founder and CEO of Drop, an electronics company that creates products powered by feedback by a massive community of enthusiasts and experts. Reflecting on his 8-year, heads-down grind since becoming a first-time founder at 22, Steve shares the lessons that he figured out the hard way, from revenue dropping off a cliff and painful pivots, to hiring blunders and severe burnout.

Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas. Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape. But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders. You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App). You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson