Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)

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/ [https://www.apple.com/] * Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ [https://www.linkedin.com/in/dennis-woodside-341302/] * Dropbox: https://www.dropbox.com/ [https://www.dropbox.com/] * Dylan Field: https://www.linkedin.com/in/dylanfield/ [https://www.linkedin.com/in/dylanfield/] * Figma: https://www.figma.com [https://www.figma.com] * Francoise Brougher: https://www.linkedin.com/in/francoise-brougher-341a72/ [https://www.linkedin.com/in/francoise-brougher-341a72/] * Gap: https://www.gap.com/ [https://www.gap.com/] * Google Chrome: https://www.google.com/chrome/ [https://www.google.com/chrome/] * Harley-Davidson: https://www.harley-davidson.com/ [https://www.harley-davidson.com/] * HubSpot: https://www.hubspot.com/ [https://www.hubspot.com/] * Notion: https://www.notion.com/ [https://www.notion.com/] * Opendoor: https://www.opendoor.com/ [https://www.opendoor.com/] * Pinterest: https://www.pinterest.com/ [https://www.pinterest.com/] * Square: https://squareup.com/ [https://squareup.com/] * The Web Is What You Make of It (Dear Sophie): https://www.youtube.com/watch?v=pzOBOuyr-EU [https://www.youtube.com/watch?v=pzOBOuyr-EU] * Urban Outfitters: https://www.urbanoutfitters.com/ [https://www.urbanoutfitters.com/] * Yamini Rangan: https://www.linkedin.com/in/yaminirangan/ [https://www.linkedin.com/in/yaminirangan/] Where to find Sheila: * LinkedIn: https://www.linkedin.com/in/sheilavashee/ [https://www.linkedin.com/in/sheilavashee/] * X: https://x.com/sheilavashee [https://x.com/sheilavashee] Where to find Brett: * LinkedIn: https://www.linkedin.com/in/brett-berson-9986644/ [https://www.linkedin.com/in/brett-berson-9986644/] * X: https://x.com/brettberson [https://x.com/brettberson] Where to find First Round Capital: * Website: https://firstround.com/ [https://firstround.com/] * First Round Review: https://review.firstround.com/ [https://review.firstround.com/] * Twitter/X: https://twitter.com/firstround [https://twitter.com/firstround] * YouTube: https://www.youtube.com/@FirstRoundCapital [https://www.youtube.com/@FirstRoundCapital] * This podcast on all platforms: https://review.firstround.com/podcast [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

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 [https://www.ahead.com] * Amazon: https://www.amazon.com [https://www.amazon.com] * Anthropic: https://www.anthropic.com [https://www.anthropic.com] * Attio: https://www.attio.com [https://www.attio.com] * Augment Code: https://www.augmentcode.com/ [https://www.augmentcode.com/] * Cognition: https://cognition.ai [https://cognition.ai] * Cursor: https://cursor.com [https://cursor.com] * Dani McCabe: https://www.linkedin.com/in/danielle-mccabe/ [https://www.linkedin.com/in/danielle-mccabe/] * Datadog: https://www.datadoghq.com [https://www.datadoghq.com] * GitHub Copilot: https://github.com/features/copilot [https://github.com/features/copilot] * HubSpot: https://www.hubspot.com [https://www.hubspot.com] * Jeremy Powers: https://www.linkedin.com/in/jeremypowers/ [https://www.linkedin.com/in/jeremypowers/] * JPMorgan: https://www.jpmorgan.com [https://www.jpmorgan.com] * Matt McClernan: https://www.linkedin.com/in/mattmcclernan/ [https://www.linkedin.com/in/mattmcclernan/] * MongoDB: https://www.mongodb.com [https://www.mongodb.com] * Nicole Rettinger: https://www.linkedin.com/in/nicole-rettinger-23b20465/ [https://www.linkedin.com/in/nicole-rettinger-23b20465/] * Notion: https://www.notion.com [https://www.notion.com] * OpenAI: https://openai.com [https://openai.com] * Parag Agrawal: https://www.linkedin.com/in/paragagr/ [https://www.linkedin.com/in/paragagr/] * Parallel: https://parallel.ai [https://parallel.ai] * Snowflake: https://www.snowflake.com [https://www.snowflake.com] * University of Chicago: https://www.uchicago.edu [https://www.uchicago.edu] * Windsurf: https://windsurf.com [https://windsurf.com] Where to find Graham: * LinkedIn: https://www.linkedin.com/in/grahammoreno/ [https://www.linkedin.com/in/grahammoreno/] Where to find Brett: * LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ [https://www.linkedin.com/in/brett-berson-9986094/] * Twitter/X: https://twitter.com/brettberson [https://twitter.com/brettberson] Where to find First Round Capital: * Website: https://firstround.com/ [https://firstround.com/] * First Round Review: https://review.firstround.com/ [https://review.firstround.com/] * Twitter/X: https://twitter.com/firstround [https://twitter.com/firstround] * YouTube: https://www.youtube.com/@FirstRoundCapital [https://www.youtube.com/@FirstRoundCapital] * This podcast on all platforms: https://review.firstround.com/podcast [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

Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)

In this latest episode of Executive Function, Brett sits down with Praveer Melwani, CFO at Figma. Praveer joined Figma in 2017 as the company's first business operations and finance hire—when the team was around 30 people and not yet charging for the product—and stepped into the CFO seat in 2022, helping to lead the company’s IPO in 2025. In today’s conversation, Praveer breaks down the step functions that took him from IC to CFO, why Figma started acting like a public company three years before IPO, and how AI is rewriting capital allocation and the CFO job itself. In today's episode, we discuss: * What separates a world-class finance leader from a traffic-cop CFO * How Praveer went from Figma's first biz ops hire to CFO of a public company in nine years * Why Figma started acting like a public company three years before its IPO * What Praveer has learned working alongside Dylan Field for nine years * Why Figma intentionally cut its 90% gross margin to invest in AI References: * Adobe: https://www.adobe.com [https://www.adobe.com] * Brendan Mulligan: https://www.linkedin.com/in/brendanmulligan [https://www.linkedin.com/in/brendanmulligan] * Cloudflare: https://www.cloudflare.com [https://www.cloudflare.com] * Dropbox: https://www.dropbox.com [https://www.dropbox.com] * Dylan Field: https://www.linkedin.com/in/dylanfield/ [https://www.linkedin.com/in/dylanfield/] * Fidelity: https://www.fidelity.com [https://www.fidelity.com] * Figma: https://www.figma.com [https://www.figma.com] * GIC: https://www.gic.com.sg [https://www.gic.com.sg] * NerdWallet: https://www.nerdwallet.com [https://www.nerdwallet.com] * Shaunt Voskanian: https://www.linkedin.com/in/shauntvoskanian/ Where to find Praveer: * LinkedIn: https://www.linkedin.com/in/praveer-melwani [https://www.linkedin.com/in/praveer-melwani] Where to find Brett: * LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ [https://www.linkedin.com/in/brett-berson-9986094/] * Twitter/X: https://twitter.com/brettberson [https://twitter.com/brettberson] Where to find First Round Capital: * Website: https://firstround.com/ [https://firstround.com/] * First Round Review: https://review.firstround.com/ [https://review.firstround.com/] * Twitter/X: https://twitter.com/firstround [https://twitter.com/firstround] * YouTube: https://www.youtube.com/@FirstRoundCapital [https://www.youtube.com/@FirstRoundCapital] * This podcast on all platforms: https://review.firstround.com/podcast [https://review.firstround.com/podcast] Timestamps: 00:00 Introduction 02:13 From banking to Dropbox to Figma 04:14 The phase shift when Figma's COO left 05:36 Hiring leaders in functions you don't understand 07:18 Selling the exec team on AI consumption pricing 09:48 Using Claude Code to learn new things as CFO 11:36 Building an internal board of peer CFOs 13:52 Inside Figma's CFO job description 16:38 What separates good CFOs from world-class CFOs 18:42 Capital allocation and risk in a post-ChatGPT world 21:45 Why Praveer wants to take more bets 24:32 How AI is materially changing the CFO role 25:36 The nine-year working relationship with Dylan Field 29:12 How deeply in the details should a CFO be? 31:47 What Dropbox taught Praveer about building strong teams 33:24 Praveer’s first-principles test for hiring VPs 38:47 Why Figma acted like a public company in 2022

Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)

In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at Google. In this conversation, she unpacks her three-bucket framework for delegating decisions, why the most important part of a CPO’s role is to drive team-wide ambition, and why the best executives need to spend half their time thinking, not doing. In today's episode, we discuss: * Why a CPO's number one job is raising their team’s ambition, not shipping features * How to demand the best from your team without creating a fear-based culture * Why organizational politics is actually an incentives problem * How Diya is “militant” with her calendar to carve out dedicated thinking time * Why you should avoid chasing titles in your career - and what to chase instead References: * Google: https://www.google.com [https://www.google.com] * Melio: https://meliopayments.com [https://meliopayments.com] * Okta: https://www.okta.com [https://www.okta.com] * Sukhinder Singh Cassidy: https://www.linkedin.com/in/sukhinders/ [https://www.linkedin.com/in/sukhinders/] * Xero: https://www.xero.com [https://www.xero.com] Where to find Diya: * LinkedIn: https://www.linkedin.com/in/diyajolly [https://www.linkedin.com/in/diyajolly] Where to find Brett: * LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ [https://www.linkedin.com/in/brett-berson-9986094/] * Twitter/X: https://twitter.com/brettberson [https://twitter.com/brettberson] Where to find First Round Capital: * Website: https://firstround.com/ [https://firstround.com/] * First Round Review: https://review.firstround.com/ [https://review.firstround.com/] * Twitter/X: https://twitter.com/firstround [https://twitter.com/firstround] * YouTube: https://www.youtube.com/@FirstRoundCapital [https://www.youtube.com/@FirstRoundCapital] * This podcast on all platforms: https://review.firstround.com/podcast [https://review.firstround.com/podcast] Timestamps: 00:12 How an excellent CPO makes an impact on the business 02:01 How the CPO role shifts under founders vs hired CEOs 03:38 Influencing a founder without going deferential 07:37 How adding value to customers is always a net positive 08:45 Why roadmaps need more risk in the AI era 12:30 How to shelter innovation teams from the existing system 15:12 What's different about being a great CPO in 2026 17:34 How AI has changed the concept of an app 18:28 It’s essential for CPOs to fly at a low altitude 20:34 How misaligned incentives cause organizational politics 25:13 Being demanding without creating a fear-based culture 28:10 Why raising ambition is a CPO's number one job 31:39 The boss who taught Diya to keep raising the bar 32:43 The hardest part of being a CPO 35:28 The three buckets Diya uses to delegate 36:30 How Diya protects deep-work time on her calendar 42:45 Xero’s game-changing early bet on AI insights 44:58 How far into the future should CPOs plan for? 47:14 What it takes to be an excellent C-suite member 48:53 Why ambitious PMs should chase impact, not titles 50:28 The four bottlenecks that stall career growth

Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)

In this episode of In Depth, First Round Partner Josh Kopelman sits down with Shachar Hirshberg and Dan Shiebler, co-founders of Artemis, the AI-native security platform that just emerged from stealth with $70M in combined seed and Series A funding. Shachar and Dan unpack how they built a 30-person team in seven months, why AI-native companies are outperforming their AI-enabled counterparts, and why they plan to stay on a texting basis with every customer, even at scale. In today's episode, we discuss: * How to interview for AI fluency when building an AI-native startup * Why founder-market fit is a critical early signal for startup success * The surprising lesson Dan learned from founder-led sales * How Dan and Shachar are instilling customer-obsession into Artemis’ culture * How the two co-founders approach conflict and decision-making References: * Abnormal: https://abnormal.ai [https://abnormal.ai] * Amazon Web Services (AWS): https://aws.amazon.com [https://aws.amazon.com] * Anthropic: https://www.anthropic.com [https://www.anthropic.com] * Artemis: https://artemissecurity.com [https://artemissecurity.com] * CrowdStrike: https://www.crowdstrike.com [https://www.crowdstrike.com] * Demisto (now Cortex XSOAR): https://www.paloaltonetworks.com/cortex/cortex-xsoar [https://www.paloaltonetworks.com/cortex/cortex-xsoar] * OpenAI: https://openai.com [https://openai.com] * Palo Alto Networks: https://www.paloaltonetworks.com [https://www.paloaltonetworks.com] * Todd Jackson: https://www.linkedin.com/in/toddj0/ [https://www.linkedin.com/in/toddj0/] Where to find Shachar Hirshberg: * LinkedIn: https://www.linkedin.com/in/shachar-hirshberg/ [https://www.linkedin.com/in/shachar-hirshberg/] Where to find Dan Shiebler: * LinkedIn: https://www.linkedin.com/in/dan-shiebler-10219b42/ [https://www.linkedin.com/in/dan-shiebler-10219b42/] Where to find Josh: * LinkedIn: https://www.linkedin.com/in/jkopelman/ [https://www.linkedin.com/in/jkopelman/] * Twitter/X: https://x.com/joshk [https://x.com/joshk] Where to find First Round Capital: * Website: https://firstround.com/ [https://firstround.com/] * First Round Review: https://review.firstround.com/ [https://review.firstround.com/] * Twitter/X: https://twitter.com/firstround [https://twitter.com/firstround] * YouTube: https://www.youtube.com/@FirstRoundCapital [https://www.youtube.com/@FirstRoundCapital] * This podcast on all platforms: https://review.firstround.com/podcast [https://review.firstround.com/podcast] Timestamps: 00:00 Introduction 00:06 What Artemis does and why now 02:51 Shachar’s AWS and Palo Alto playbook 05:15 Dan’s founder journey: From Twitter to Abnormal 08:51 Why founder-market fit is critical for startups 11:38 Finding the right moment to take the leap and build 13:52 The hiring process that powers a startup in stealth 16:58 Building a team centered on AI capabilities 21:48 How AI implementation changes dashboard metrics 23:22 The ICP they chased and the one they ignored 26:44 The magic of closing the first customers 27:49 The surprising signals of early product-market fit 32:06 Critical lessons from founder-led sales 33:51 Why the first product should make founders uncomfortable 36:03 Hiring 30 people while still in stealth 42:08 “Should we be arguing more?” 43:37 How the AI security market is evolving 49:03 Why AI-native beats AI-enabled company structure 51:09 The most surprising moments as a first-time founder