In Depth

For our 60th episode, we’re doing things a little bit differently — with a new guest host! Welcome to Todd Jackson, who’s filling in for Brett Berson this week. Todd is also a Partner at First Round, and the episodes he hosts will mostly focus on product, given his previous product roles, from the VP of Product & Design at Dropbox and Director of Product Management at Twitter, to being a PM at Fac...

Today’s episode is with Russ Laraway, a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital Since we last had Russ on the show, he’s written a new book, titled: “When They Win, You Win.” On today’s episode, we dive deep into the management frameworks and original research that Russ discusses in his book. He starts by point...

Today’s episode is with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. In today’s conversation, we cover his essential advice for building a highly-technical product. He sketches out how the Cockroach team decided on the specific use case for its database product. Nate explains the steps the team took to reach conviction on their go-forward plan — which meant say...

Today’s episode is with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. In today’s conversation, Phaedra explores the ins and outs of selling a product into government. Phaedra pulls back the curtain of how she and the Promise team tackle the extra-long sales cycles, navigate layers of subcontractors, and convince risk-averse decision-makers to take a ch...

Today’s episode is with Gagan Biyani, co-founder and CEO of Maven, a company that empowers the world’s experts to offer cohort-based courses directly to their audience. After being early at 3 startups that achieved over $1 million in run-rate in their first six months of going live, Gagan has learned some valuable lessons and seen a wide range of outcomes — from Udemy going on to IPO in 2021, to S...

Today’s episode is with Kaitlyn Knopp, founder and CEO of Pequity, which automates HR workflows to make compensation more equitable and scalable. Prior to starting Pequity, Kaitlyn built compensation programs and teams at companies like Instacart, Cruise, and Google — bringing a deep well of experience to this often complicated topic. We start our conversation with her advice on the traps founders...

Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma. Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She wa...

Today’s episode is with Jack Altman, co-founder & CEO of Lattice. There were so many topics we could have gotten into with Jack as it relates to scaling as a founder and CEO, but we decided to dive deep on executive hiring, a huge challenge for founders.  The conversation starts with how the hiring profile for executives changes as the company grows. Jack is a strong believer that you should focus...

Today’s episode is with Amber Feng, who is the co-founder and CTO of Cocoon, and was previously an engineering leader at Stripe for eight years. In today’s conversation, we pull on threads from Amber’s engineering career to weave together lessons for other engineers charting their own path. Although Amber’s spent the majority of her career at Stripe, she’s had all sorts of different experiences —...

Today’s episode is with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor. Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website vi...

Today’s episode is with Max Rhodes, the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar. In today’s conversation, we dive deep into h...

Today’s episode is with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth for Stripe, where she’s responsible for all sales functions and leads the company’s enterprise strategy. She joined Stripe after a career in sales at Google and also serving as Dialpad’s Chief Revenue Officer. In today’s conversation, we dive super deep into all things pricing. To start, Jeanne outlines the trade-of...

Today’s episode is with Ravi Mehta, who is formerly the Chief Product Officer at Tinder, and taught product strategy as an Executive in Residence at Reforge. In today’s conversation, we dive exceptionally deep into product strategy, starting with what Ravi sees as the most common disconnect between product strategy and what product teams actually work on day-to-day. In the bulk of our discussion,...

Today’s episode is with Arielle Jackson. For the past 7 years, she’s helped hundreds of companies build their positioning and brands from the ground up, both as our Marketing Expert in Residence here at First Round and in her own consulting work. Before helping early-stage startups, Arielle started her career in Product Marketing at Google, where she helped launch and grow Google Books and AdWords...

Today’s episode is with Adrian McDermott, CTO of Zendesk. Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees. Our discussion digs into the challenges that come from scaling startups. We start off by diving into a common decision point: whether to...

Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to incre...

Today’s episode is with Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation. Zach was one of Canva's first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done...

Today’s episode is with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment. In today’s conversation, we deeply explore Hareem’s three pillars of what makes a great designer. To summarize, they are a product quality ambassador, serve as the glue across...

Today’s episode is with Max Mullen, co-founder of Instacart. He started as a generalist, running everything from product to payroll, but as the company has grown over the years, he’s come to focus on one particular area: culture. Since Max is also an active angel investor, he’s also been able to partner with tons of founders and help them think about architecting their own culture at the early sta...

Today’s episode is with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week.  In our conversation today, we focus on what founders and startup leaders can learn from Alisa’s experiences as a coa...

Today’s episode is with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund. In today’s conversation, we dive really deep into what she’s learned about executive hiring. To start, she explains how to align the hiring...

Today’s episode is with Giancarlo 'GC' Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.) He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a uniq...

Today’s episode is with Sandr Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. Sandra started KiwiCo over ten years ago, after a career with executive positions at PayPal and eBay. She was looking for ways to give her own kids more hands-on projects to exercise their creativity, which led her down the path to become an entrepreneur and create KiwiCo. Today, Kiw...

Today’s episode is with Maya Spivak, the Head of Marketing at Mux, which is ​​an API for developers to build video experiences. Maya recently joined Mux after five years at Segment, where she was the company’s second marketer and its Head of Global Brand Marketing and Communications, as well as a stint at Wealthfront as a marketing director. In today’s conversation, she takes a magnifying glass to...

Today’s episode is with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. Archana joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk. We start today’s conversation by dissecting some of the messaging challenges facing horizonta...