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by First Round
Welcome to In Depth, a podcast that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found.
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- 1 weeks ago47 min
Competing with OpenAI and Meta for your inbox | Jean-Denis Greze (Town Co-founder & CEO)
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
- Aug 27, 20261h 2m
The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)
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
- Jul 30, 20261h 8m
What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)
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
- Jul 24, 20261h 2m
How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
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
- Jul 16, 20261h 9m
Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)
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
- Jun 25, 202659 min
How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)
In this episode of In Depth, Brett sits down with Paul Copplestone, co-founder and CEO of Supabase, the open-source Postgres platform now serving more than seven million developers. Before Supabase, Paul launched a Thumbtack-style marketplace in Southeast Asia and co-founded an office-management startup called Nimbus, experiences that taught him to separate fundraising from building and to find product-market fit before blitzscaling. He breaks down how a single tagline change for Supabase unlocked product-market fit, why he runs a fully distributed async team with near-zero attrition, and how he turned PLG signals into a product-led sales motion comped only on incremental uplift. In today's episode, we discuss: How changing one tagline helped Supabase go to #1 in Hacker News - an early sign of product market fit Why Paul ran Supabase like it had only $100K in the bank despite raising real money How Supabase rode three distinct AI waves, from pgvector to Bolt and Lovable, to Claude Code Why Supabase built a sales team comped only on the incremental uplift over a control group What the Toyota production system's "kaizen" taught Paul about unblocking a scaling team References: Ant Wilson: https://www.linkedin.com/in/ant-wilson-46179937 Bolt: https://bolt.new/ Claude Code: https://www.anthropic.com/claude-code Codex: https://openai.com/codex/ Entrepreneurs First: https://www.joinef.com/ Firebase: https://firebase.google.com/ Lovable: https://lovable.dev/ MongoDB: https://www.mongodb.com/ Next.js: https://nextjs.org/ PostgreSQL: https://www.postgresql.org/ Supabase: https://supabase.com/ Thumbtack: https://www.thumbtack.com/ Y Combinator: https://www.ycombinator.com/ Where to find Paul: LinkedIn: https://www.linkedin.com/in/paulcopplestone Twitter/X: https://x.com/kiwicopple 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 01:32 Why Paul's earlier startups were never destined to be huge 07:14 Unlearning the "tall poppy" mindset and going all-in on async 09:54 Reverse-engineering why Supabase was an outstanding idea 12:04 The accidental Hacker News launch and tagline lesson 13:58 Where the early roadmap came from: demand vs. technical taste 17:28 Skill vs. luck, and operating like you have $100K in the bank 21:42 What actually makes a great developer experience 23:10 Solving the "graduation problem" Firebase never could 24:58 The role of open source in Supabase's success 26:10 The three distinct AI tailwinds: From pgvector to Claude Code 35:24 Supabase’s egoless, hyper-competitive open-source culture 42:58 A tactical playbook for raising capital 48:37 Product-led sales comped on incremental uplift only 59:27 The production philosophy behind Supabase’s operations
- Jun 4, 20261h 0m
How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)
In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads marketing at Figma fresh off its IPO. In an industry that has spent a decade trying to turn marketing into something closer to hedge fund trading, Sheila argues the art was always the point — we just stopped talking about it. She unpacks how to run marketing as a portfolio of moonshots, why giving teams different goals breeds dysfunction, how to scale taste across an organization, and why old playbooks are obsolete, even as the fundamentals hold. In today's episode, we discuss: How to run marketing like a portfolio of moonshots The value of disruptive energy for senior marketers Why "Ubiquity is the opposite of cool" How to actually scale taste across an organization What great marketing looks like in the AI era Referenced: Apple: https://www.apple.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ Figma: https://www.figma.com Francoise Brougher: https://www.linkedin.com/in/francoise-brougher-341a72/ Gap: https://www.gap.com/ Google Chrome: https://www.google.com/chrome/ Harley-Davidson: https://www.harley-davidson.com/ HubSpot: https://www.hubspot.com/ Notion: https://www.notion.com/ Opendoor: https://www.opendoor.com/ Pinterest: https://www.pinterest.com/ Square: https://squareup.com/ The Web Is What You Make of It (Dear Sophie): https://www.youtube.com/watch?v=pzOBOuyr-EU Urban Outfitters: https://www.urbanoutfitters.com/ Yamini Rangan: https://www.linkedin.com/in/yaminirangan/ Where to find Sheila: LinkedIn: https://www.linkedin.com/in/sheilavashee/ X: https://x.com/sheilavashee Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986644/ X: https://x.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 00:07 What excellent marketing actually is in 2026 01:36 Why giving teams different goals creates dysfunction 02:36 The most important decision Sheila made as CMO last year 04:26 The real difference between an SVP and a CMO 06:05 Marketing is one engine - not separate pieces 07:15 The tension between brand and growth 09:25 The decisions a CMO should never be making 09:55 Running marketing like a portfolio of moonshots 12:46 "Ubiquity is the opposite of cool" 15:11 Why a few companies get a flywheel of momentum 16:44 The Silicon Valley clock and irrational perception cycles 19:25 How to actually scale taste across an org 21:09 What changes for a CMO in a post-LLM world 23:15 Why the artistic side of marketing never really left 26:05 Whether taste can ever be encoded in software 27:15 Telling an optimistic, yet realistic story about AI 30:50 You need to make people care 32:11 What surprised Sheila about being a public-company CMO 33:46 Why Figma won enterprise where Dropbox couldn't 35:25 Sheila’s favorite campaign ever 37:10 Why announcement videos full of humans, lack humanity 38:55 Playbooks are obselete, but the fundamentals are not 40:25 Why marketing in 2026 demands disruptive energy 41:54 How Sheila architects her week 48:55 Where corporate politics actually come from 53:55 "Sheila, are you going to change the world in this job?" 58:09 What's unique about the CMO and CEO relationship
- May 21, 20261h 2m
Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to seventy-five in under a year, served as President through the Cognition acquisition, and earlier built and led enterprise sales teams at Grafana Labs and MongoDB. In this conversation, he unpacks why the AI-era backlash against structured enterprise sales misreads the data, how to design a process that raises the floor for ordinary reps without capping the ceiling for stars, and why selling to AI-native customers compresses an eight-week cycle into five business days. In today's episode, we discuss: Why in-person enterprise rollouts still beat product-led motions Building a robust sales process that still leaves room for unscripted moments Why the three highest-leverage early sales hires aren't sellers at all The case for outsized commission accelerators for star sellers — and the kind of person they attract Why most AI companies are skipping the in-person sales work that enterprise customers actually want References: Ahead: https://www.ahead.com Amazon: https://www.amazon.com Anthropic: https://www.anthropic.com Attio: https://www.attio.com Augment Code: https://www.augmentcode.com/ Cognition: https://cognition.ai Cursor: https://cursor.com Dani McCabe: https://www.linkedin.com/in/danielle-mccabe/ Datadog: https://www.datadoghq.com GitHub Copilot: https://github.com/features/copilot HubSpot: https://www.hubspot.com Jeremy Powers: https://www.linkedin.com/in/jeremypowers/ JPMorgan: https://www.jpmorgan.com Matt McClernan: https://www.linkedin.com/in/mattmcclernan/ MongoDB: https://www.mongodb.com Nicole Rettinger: https://www.linkedin.com/in/nicole-rettinger-23b20465/ Notion: https://www.notion.com OpenAI: https://openai.com Parag Agrawal: https://www.linkedin.com/in/paragagr/ Parallel: https://parallel.ai Snowflake: https://www.snowflake.com University of Chicago: https://www.uchicago.edu Windsurf: https://windsurf.com Where to find Graham: LinkedIn: https://www.linkedin.com/in/grahammoreno/ 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 00:32 Has the sales playbook changed in the AI era? 02:13 Why "showing up" beats letting the marketplace decide 06:50 Why great salespeople sell to engineers and executives in one motion 11:37 Selling to AI-native buyers who grew up on ChatGPT 13:49 Same seller, different tempo: 8 weeks vs. 8 business days 15:57 How AI-native buyers handle build vs. buy decisions 17:48 The rep who taught a champion's son guitar over Zoom 19:03 Raising the floor without capping the ceiling 22:09 Why too much process narrows the kind of seller you attract 25:46 The three pillars of GTM excellence 31:00 Building peers who are 80% aligned, not 100% 38:03 Whether AI is changing what good enablement looks like 41:35 Selling against direct and implied competitors at once 42:45 Instrumenting the funnel from stage zero to close 45:57 Why post-sales should always roll up to the revenue leader 48:19 The case for outsized commissions 52:02 The 96 hours of panic before Cognition acquired Windsurf 53:04 How far out should a GTM leader be planning? 57:53 What a normal week looks like in hypergrowth
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About In Depth
Welcome to In Depth, a podcast that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found.
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