In Depth

In this episode of In Depth, Todd sits down with Jean-Denis Greze, co-founder and CEO of Town, the AI work assistant that gives every employee their own agent. Before Town, Jean-Denis spent seven years as CTO of Plaid and led engineering teams at Dropbox, where he and Todd first worked together. In this conversation, they dive into what it takes to build in tech's hottest category while competing with Microsoft, Google and the frontier labs, why Town bet on work agents over personal agents, and how to get agents to share the right information with each other.   In today's episode, we discuss: The edge that keeps Town competitive with Google and Microsoft How user feedback adjusted Town’s product Why Jean-Denis believes people will start delegating decision-making to AI What a multiplayer AI assistant world looks like Why Town started rolling back its guardrails after users approved 95% of agent actions   References: Anthropic: https://www.anthropic.com/ Bret Taylor: https://www.linkedin.com/in/brettaylor/ Dropbox: https://www.dropbox.com/ Facebook: https://www.facebook.com/ Figma: https://www.figma.com/ Glean: https://www.glean.com/ Google: https://www.google.com/ HubSpot: https://www.hubspot.com/ Instinct: https://instinct.com/ Meta: https://www.meta.com/ Microsoft: https://www.microsoft.com/ OpenAI: https://openai.com/ Plaid: https://plaid.com/ Salesforce: https://www.salesforce.com/ Sierra: https://sierra.ai/ Slack: https://slack.com/ Town: https://www.town.com/   Where to find Jean-Denis: LinkedIn: https://www.linkedin.com/in/jeandenisgreze Twitter/X: https://x.com/jgreze   Where to find Todd: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://x.com/tjack   Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://x.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 01:28 Competing in the AI agent race 03:23 Why people will run two AI assistants 07:01 Why personal AI hits a ceiling and work AI doesn't 09:08 What made always-on agents possible now 15:54 Building on labs that compete with you 17:57 Pricing tokens instead of outcomes 22:52 How Town's users drive new features 25:08 Why Town is actually an AI onboarding platform 27:15 What a design-minded co-founder brings 29:13 The one-agent-per-person debate 30:59 Why Town pivoted from tax to AI assistants 32:01 Designing an agent people can trust 35:27 How multiplayer changes privacy 44:33 Why AI should choose what you share with coworkers

In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft. Before joining Microsoft, Jay spent over a decade as Facebook's global head of engineering, scaling the company from a few hundred engineers to billions of users, then ran the cybersecurity company Lacework as CEO through its acquisition by Fortinet. In this conversation, he breaks down the five ingredients of great engineering leadership, discusses why he'd rather run two competing bets in parallel than forecast a winner, and explains why company culture remains more important than ever for teams to get right. In today's episode, we discuss: The five ingredients that separate excellent engineering leadership from the rest How to protect your team from large shifts in public perception The mindset shift organizations need to maintain speed at scale How every layer of the organization needs to stay connected to the customer Why Jay runs "brain trusts" of senior ICs with zero managers in the room References Akamai: https://www.akamai.com/ AWS: https://aws.amazon.com/ Facebook: https://www.facebook.com/ George Conrades: https://www.linkedin.com/in/georgeconrades/ Mark Zuckerberg: https://x.com/finkd Microsoft: https://www.microsoft.com/ Paul Sagan: https://www.linkedin.com/in/paul-sagan-59654a1/ Tom Leighton: https://www.linkedin.com/in/tleighton/ Where to find Jay LinkedIn: https://www.linkedin.com/in/jayparikh/ Twitter/X: https://x.com/jayparikh Where to find Brett LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps 00:00 Introduction 00:36 How leadership changes through exponential growth 02:21 The five ingredients that define excellent engineering leadership 07:51 What actually drives culture at a company as it scales 12:05 The physics behind why everything slows down at scale 18:57 The fastest team of Jay's career, and why size mattered 22:44 Why every team should think like an FDE 26:20 Managing a team through wild swings in public perception 29:07 What's different about leading through the steepest S-curve moments 33:58 Why onboarding well means going slow to go fast 37:41 Is AI actually new, or is history just repeating? 41:35 What actually counts as a "big bet" worth taking 45:01 The concrete big bets that reshaped Facebook's entire technology stack 47:35 Why vertical integration keeps being the right call as companies scale 51:46 How being a startup CEO reshaped Jay as a leader 1:01:26 Why Jay overruled Zuckerberg's instinct to skip efficiency

In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Checkr rebuilt its sales compensation model to keep pace with growth, and where AI is already reshaping her operations and go-to-market teams. In today's episode, we discuss: Why operators who thrive at massive-scale companies often struggle when they join a startup The hard-won lessons from Checkr's early enterprise push that nearly failed Why Checkr’s C-suite meets every morning with no specific agenda The surprising challenges moving from CRO to COO How Checkr turned AI experiments into operating systems References Amazon: https://www.amazon.com Checkr: https://checkr.com Claude: https://claude.com Daniel Yanisse: https://www.linkedin.com/in/yanisse/ DoorDash: https://www.doordash.com Google: https://www.google.com Lovable: https://lovable.dev Microsoft: https://www.microsoft.com Where to find Lindsey LinkedIn: https://www.linkedin.com/in/lindsey-scrase-0702442/ Twitter/X: https://twitter.com/Lscrase Where to find Brett LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps 00:00 Introduction 00:06 Why big-company executives often struggle in startups 02:18 What Checkr's first CRO needed to accomplish 03:33 How to take on an entrenched category leader 06:58 Why leaders underestimate how hard the jump to enterprise really is 10:23 Separating a true deal-blocker from a customer's nice-to-have request 18:30 Why Lindsey hired enterprise-scarred sales leader over a market leader's résumé 22:08 The biggest challenges of moving from CRO to COO 28:03 Why Checkr names a single decision-maker for every major decision 34:42 Why Checkr rebuilt their sales compensation model 40:39 What actually separates a team's best seller from everyone else 45:03 Inside Checkr’s daily, no-agenda, c-suite meeting 50:23 How following data can sometimes lead you in the wrong direction 57:27 Why hitting 130% of a goal isn’t always a good thing 58:57 Where AI has changed how Checkr's teams operate day to day 1:04:33 Advice for all aspiring COOs

In this episode of In Depth, Brett sits down with Jon Noronha, co-founder and CPO of Gamma, the AI-native presentation platform used by more than 100 million people. In this conversation, he walks through Gamma’s distinct eras of product-market fit: from a pre-AI struggle with a year of runway left, to an overnight AI-fueled explosion, to today’s unplanned scramble into enterprise sales. Jon also unpacks his hard-won lessons on horizontal versus vertical bets, monetizing AI products, and why nailing onboarding turned out to be the whole game. In today's episode, we discuss: Why Gamma's all-in AI launch in March 2023 saved their startup How fixing a simple onboarding problem accidentally uncovered Gamma’s entire product-market fit Why Jon bet Gamma on a horizontal product against the advice of nearly every investor How Gamma's daily signups climbed from hundreds to over 100,000 with zero paid marketing What building three pricing tiers taught Jon about monetizing AI References Canva: https://www.canva.com/ Corgi: https://www.corgi.insure/ Facebook: https://www.facebook.com/ Gamma: https://gamma.app/ Google: https://www.google.com/ Linear: https://linear.app/ Loom: https://www.loom.com/ Microsoft: https://www.microsoft.com/ Notion: https://www.notion.com/ Optimizely: https://www.optimizely.com/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ Zoom: https://www.zoom.us/ Where to find Jon Noronha LinkedIn: https://www.linkedin.com/in/jonnoronha/ Twitter/X: https://twitter.com/thatsjonsense Where to find Brett LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 01:47 Gamma’s three-era journey to product-market fit 03:41 Spotting the blank page problem pre-ChatGPT 05:11 How Gamma survived with only one year of runway 07:17 How onboarding fixes revealed the whole product 09:31 Choosing horizontal over investors' vertical playbook 13:41 Prototyping by hand before AI coding 15:36 How Gamma builds with future models in mind 20:06 The Kool-Aid mistake of a late PowerPoint export 24:31 Why the presentation industry hadn't evolved since 1987 33:30 How Gamma solves evals for taste, not just data 40:21 Jon's hardest lessons monetizing AI since 2023 44:16 The fast leap from prosumer to enterprise 47:01 Why product still beats distribution 52:06 The metric that proved product-market fit 57:36 Pricing advice for prosumer AI founders 59:01 The toils and realities of founder life

In the latest episode of Executive Function, Brett sits down with Eric Sager, COO of Plaid, following stints as CRO of Bluevine and Head of Sales at Square. During his seven-year tenure at Plaid, Eric has helped lead the business through a pandemic, Visa's collapsed acquisition, a fintech downturn, and the AI boom. In today’s conversation, he unpacks how he kept teams focused during turbulent times, why he refuses to run at 100% capacity, and how he re-architected the go-to-market function as Plaid scaled. In today's episode, we discuss: How Plaid stayed focused after the Visa acquisition fell through and then raised at nearly 3x the price Why great COOs deliberately make themselves obsolete Why Eric treats speed, risk, and cost as a three-way trade-off, and why sometimes going slower wins How refusing to run at 100% capacity helped Plaid win OpenAI, Perplexity, and Replit Why Eric personally cold-calls brand-new employees References Bain & Company: https://www.bain.com Bluevine: https://www.bluevine.com Chase: https://www.chase.com Citibank: https://www.citi.com Eyal Lifshitz: https://www.linkedin.com/in/eyallifshitz/ Françoise Brougher: https://x.com/FrancoiseBr Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Jack Dorsey: https://x.com/jack Michael Mankins: https://www.linkedin.com/in/michaelcmankins OpenAI: https://openai.com Perplexity: https://www.perplexity.ai Plaid: https://plaid.com Replit: https://replit.com Sarah Friar: https://www.linkedin.com/in/sarah-friar/ Square: https://squareup.com Visa: https://www.visa.com William Hockey: https://www.linkedin.com/in/william-hockey-04536710 Zach Perret: https://www.linkedin.com/in/zperret/ Where to find Eric Sager LinkedIn: https://www.linkedin.com/in/eric-sager-a529516 Where to find Brett LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps 00:00 Introduction 00:40 Leading a company through turbulent times 04:24 How to build a resilient team culture 08:33 How Plaid avoids bureaucracy, while operating at scale 10:58 The speed-quality tradeoff: Going faster isn't always better 15:32 When to move from generalists to specialized customer segments 20:14 Why Plaid has one owner for entire customer relationships 22:06 The "quarterback" model: one owner, experts on call 24:08 Why you should never run your org at 100% capacity 29:47 "Always available, never needed": the support mantra 36:49 Eric’s unusual "hit by a bus" test to measure job success 43:57 Why Eric cold calls brand-new employees 52:14 Eric's week: 25% ecosystem, 50% business, 25% team 55:15 How to spot fake mission alignment in interviews 59:04 The one thing a founder has that no hire can replicate