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 Melio: https://meliopayments.com Okta: https://www.okta.com Sukhinder Singh Cassidy: https://www.linkedin.com/in/sukhinders/ Xero: https://www.xero.com Where to find Diya: LinkedIn: https://www.linkedin.com/in/diyajolly 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: 00:12 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

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 Amazon Web Services (AWS): https://aws.amazon.com Anthropic: https://www.anthropic.com Artemis: https://artemissecurity.com CrowdStrike: https://www.crowdstrike.com Demisto (now Cortex XSOAR): https://www.paloaltonetworks.com/cortex/cortex-xsoar OpenAI: https://openai.com Palo Alto Networks: https://www.paloaltonetworks.com Todd Jackson: https://www.linkedin.com/in/toddj0/ Where to find Shachar Hirshberg: LinkedIn: https://www.linkedin.com/in/shachar-hirshberg/ Where to find Dan Shiebler: LinkedIn: https://www.linkedin.com/in/dan-shiebler-10219b42/ Where to find Josh: LinkedIn: https://www.linkedin.com/in/jkopelman/ Twitter/X: https://x.com/joshk 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 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

In this latest episode of Executive Function, Brett sits down with Christopher Payne, who spent a decade as President and COO at DoorDash, helping scale the company from roughly 70 employees to the dominant food delivery platform in the US. Before DoorDash, Christopher held senior operating roles at Amazon and eBay, where he led a sweeping overhaul of marketplace search. In this conversation, he unpacks what it actually takes to run an atoms-based business versus a software company, shares his "plate spinning" framework for allocating executive attention across a complex org, and makes the case for top-down goal setting over the bottom-up alternative. In today's episode, we discuss: How prior industry experience can be a liability when you're trying to reinvent the market How executives can practically focus their attention to stay close to product details What charisma actually looks like in executives—and why it's a staple trait to have The business case for setting ambitious goals top-down, not bottom-up References: Amazon: https://www.amazon.com/ Anthropic: https://www.anthropic.com/ Cheesecake Factory: https://www.thecheesecakefactory.com/ Cursor: https://cursor.com/ Dartmouth College: https://home.dartmouth.edu/ David Risher: https://www.linkedin.com/in/jdavidrisher DoorDash: https://www.doordash.com/ eBay: https://www.ebay.com/ Granola: https://www.granola.ai/ Hulu: https://www.hulu.com/ Jason Kilar: https://www.linkedin.com/in/jasonkilar Jeff Bezos: https://x.com/JeffBezos Lyft: https://www.lyft.com/ Microsoft: https://www.microsoft.com/ Tinder: https://tinder.com/ Tony Xu: https://www.linkedin.com/in/xutony Travis Kalanick: https://www.linkedin.com/in/traviskalanick Uber: https://www.uber.com/ University of Oregon: https://www.uoregon.edu/ Wharton School: https://www.wharton.upenn.edu/ Where to find Christopher Payne: LinkedIn: https://www.linkedin.com/in/christopherpayne Twitter/X: https://x.com/chrispa 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 00:14 Why atoms businesses challenge bits executives 02:35 Hiring executives with a builder mentality 06:52 Great executives never outgrow the details 08:05 How ciabatta bread revealed a core DoorDash issue 10:48 How executives can scale their own impact 14:22 One-size-fits-all management is a myth 19:01 Enduring business lessons from Jeff Bezos 20:56 “I was fired from Tinder after six months” 25:38 Why specializing too early is a leadership trap 27:41 Are competitive cultures essential for success? 31:00 Lessons from Amazon’s hypergrowth 35:20 Why having industry experience can be a liability 38:46 Companies spend too much time on job interviews 40:19 The skills executives need for hypergrowth 43:34 Why AI will likely flatten organizations 45:20 Teaching COO 101: What it takes to be world-class 50:55 Why bottom-up goal setting kills ambition 55:29 How charismatic leaders help teams in tough times 58:23 The number-one sign of high-functioning executive teams 1:02:02 How first-time COOs can increase their chance of success

In the latest episode of Executive Function, Brett sits down with Katie Burke, who recently became COO of Harvey after joining as Chief People Officer. Before Harvey, Katie spent 11 years in HR leadership at HubSpot, where she built one of tech's most distinctive cultures. In this conversation, she unpacks her marketing-minded approach to HR, why she hired deliberately from hospitality rather than corporate backgrounds, and why developing culture should be a strategic priority for any organization. In today's episode, we discuss: Why HR leaders should think like marketers The 2.5-year cultural hangover after a layoff The protein vs. sugar rule for employee feedback What it means to be the executive team’s own HR business partner What the Chief People Officer owes the board and what they don't References: Amazon: https://www.amazon.com Anique Drumright: https://www.linkedin.com/in/anique-drumright-53978a1a/ Brian Halligan: https://www.linkedin.com/in/brianhalligan/ Carmel Galvin: https://www.linkedin.com/in/carmelgalvin/ eBay: https://www.ebay.com Gabe Pereyra: https://www.linkedin.com/in/gabepereyra Harvey: https://www.harvey.ai HubSpot: https://www.hubspot.com Jacqui Canney: https://www.linkedin.com/in/jacquicanney Klaviyo: https://www.klaviyo.com Lorrie Norrington: https://www.linkedin.com/in/lorrienorrington/ Maggie Landers: https://www.linkedin.com/in/maggiecohenlanders/ Rippling: https://www.rippling.com ServiceNow: https://www.servicenow.com Winston Weinberg: https://www.linkedin.com/in/winston-weinberg/ Where to find Katie: LinkedIn: https://www.linkedin.com/in/katie-burke-965767a/ Twitter/X: https://x.com/katieburkie 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 00:23 Why HR begins with thinking like a marketer 01:58   “Don't ask for a seat at the table. Build the table.” 02:29 Radical transparency after Hubspot’s IPO 05:14 How HubSpot’s people function drove strategy 07:01 The trickiest part of the Chief People Officer role 10:00 Be the Michael Jordan of your exec team 12:14 Why people leaders need to create “graceful exits” 16:49 The inevitable two-year layoff hangover 23:31 The workplace shouldn’t be Disneyland 26:05 “Our job is not to make you happy every day” 34:28 Being a Chief People Officer isn’t for the faint of heart 35:04 How “Berry-Gate” taught HubSpot to manage feedback 40:51 Chief People Officers should be demanding, by design 42:01 Why “frequent flyers” are a new-hire red flag 44:54 Unpacking the role of the VP of People 49:94 Which company decisions fall to the Chief People Officer? 49:11 The most common challenges of scaling a company 51:39 The differences between HubSpot and Harvey 53:17 How AI is changing the people function 1:04:28 Why Katie shares her own performance reviews 1:06:22 How to manage a disagreement with the CEO

Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition. In this episode, we discuss: Why moving from software engineer to CEO requires almost an entirely new skillset The product marketing pyramid Jay built to explain Kafka to the world How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing” The critical difference between what a company can do and what it must do What keeps scaling companies from becoming "Chipotle” References: Amazon Web Services: https://aws.amazon.com/ Apache Kafka: https://kafka.apache.org/ Benchmark: https://www.benchmark.com/ Confluent: https://www.confluent.io/ Jun Rao: https://www.linkedin.com/in/junrao LinkedIn: https://www.linkedin.com/ McKinsey & Company: https://www.mckinsey.com/ MySpace: https://www.myspace.com/ Neha Narkhede: https://www.linkedin.com/in/nehanarkhede Oracle: https://www.oracle.com/ Red Hat: https://www.redhat.com/ Snowflake: https://www.snowflake.com/ Where to find Jay: LinkedIn: https://www.linkedin.com/in/jaykreps/ Twitter/X: https://x.com/jaykreps 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: 01:18 Making the leap from engineer to CEO 03:33 The 80% rule: what a CEO actually needs to know 04:54 Scaling different business disciplines 09:31 How Confluent’s story began in LinkedIn 12:13 The growing need for scalable data tech 13:37 What the early Kafka product looked like 16:38 Kafka’s underwhelming open-source launch 18:38 The blog post that accelerated Kafka’s adoption 20:16 Why so many marketing messages fail 28:08 The decision to build Confluent 34:24 Planning to fundraise before building the product 39:19 Confluent’s early years: Tough product decisions 47:07 The underrated growth lever question for companies 55:46 Why founder optimism is an overrated trait 1:00:29 What should founders give up as they scale? 1:02:47 Why people become trapped in a failure mindset 1:08:33 The Chipotle problem: Losing excellence at scale

In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you. In today's episode, we discuss: The mindset shift that made Jeremy's transition to startup CPO work Why it’s essential for the CPO to stay connected to details The rule to ensure teams ship fast while growing quickly Why rigid hierarchies derail quality decision-making How Jeremy uses open office hours for the entire company References: Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Dropbox: https://www.dropbox.com GitHub: https://www.github.com Ironclad: https://www.ironcladapp.com Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Lovable: https://lovable.dev Microsoft: https://www.microsoft.com Nat Friedman: https://www.linkedin.com/in/natfriedman/ NVIDIA: https://www.nvidia.com Span: https://www.span.app/ v0: https://v0.dev Vanta: https://www.vanta.com Where to find Jeremy: LinkedIn: https://www.linkedin.com/in/jeremy-epling-j40/ Twitter/X: https://x.com/jeremy_epling 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 00:09 Why most big-tech executives fail at startups 05:38 Great product leaders stay in the details 09:21 The biggest mindset shift from VP to CPO 16:24 Revenue and product teams are always at odds 18:00 The key to a quality CPO and CRO relationship 23:21 Stop making your team fetch rocks 25:54 Who ultimately oversees the quality bar? 32:27 Why rigid hierarchies kill great companies 36:38 How to leave actionable, detailed feedback 38:55 Great CPOs should avoid comfort metrics 47:27 A glimpse into Jeremy’s working week 49:07 The case for weekly 1:1s 55:13 Why ICs are the unsung heroes of a company 58:25 Jeremy’s most formative career moments 1:07:55 The hardest skills Jeremy had to learn 1:09:31 Why great managers know when to push

Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown. In today's episode, we discuss: Why Zipline hires teenagers over PhDs Why the best startup employees are "heat-seeking missiles for pain" The 5 leadership attributes Zipline has never shared publicly The brutal firing advice that shaped Keller’s leadership How Rwanda’s health minister changed Zipline’s trajectory References: Airbnb: https://www.airbnb.com Alfred Lin: https://www.linkedin.com/in/linalfred/ Amazon: https://www.amazon.com Apple: https://www.apple.com Brian Chesky: https://www.linkedin.com/in/brianchesky/ Cleveland Clinic: https://my.clevelandclinic.org Netflix: https://www.netflix.com Paul Kagame: https://www.linkedin.com/in/paulkagame/ Reflect Orbital: https://www.reflectorbital.com Sequoia Capital: https://www.sequoiacapital.com SpaceX: https://www.spacex.com Sphero: https://www.sphero.com Tesla: https://www.tesla.com University of Washington: https://www.washington.edu Walmart: https://www.walmart.com Zipline: https://www.zipline.com Where to find Keller: LinkedIn: https://www.linkedin.com/in/kellerrc/ Twitter/X: https://x.com/Keller 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 02:11 Why Zipline doesn't hire for experience 06:04 Are founders born or made? 07:37 Why Zipline hires 17-year-olds over PhDs 17:03 The employees Zipline doesn't want 18:53 The ultimate startup hire is a "heat-seeking missile" 20:36 Why blind references are a non-negotiable 23:07 Can candidates admit when they screwed up? 30:10 Zipline's secret leadership playbook 35:16 Why you should always fire quickly 36:26 The early vision for Zipline 39:48 How Zipline almost died - twice 44:55 From toy robots to drone delivery: Zipline's pivot 51:35 How Rwanda's health minister changed everything 57:10 Why Zipline's launch was a "complete disaster" 1:04:05 Scaling from 1 hospital to 5000 1:05:17 The 10x hardware cost rule every founder should know

Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team. In today's episode, we discuss: What the CRO job looks like at $10M vs. $1B+ Why sales leaders must know how to sell the product themselves The MEDDIC methodology and why it's a founder's best insurance policy How to find the fakers, manage-uppers and passengers in your org What Frank Slootman got right — and wrong — about scaling Snowflake Why most AI companies will face a go-to-market reckoning References: Amazon: https://www.amazon.com/ Bob Muglia: https://www.linkedin.com/in/bob-muglia-714ba592/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Christian Kleinerman: https://www.linkedin.com/in/christian-kleinerman-a973102/ Denise Persson: https://www.linkedin.com/in/denisepersson/ Dell: https://www.dell.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ John McMahon: https://www.linkedin.com/in/johnmcmahon1/ Michael Scarpelli: https://www.linkedin.com/in/michael-scarpelli-1b289b9/ Microsoft: https://www.microsoft.com/ Oracle: https://www.oracle.com/ Salesforce: https://www.salesforce.com/ Snowflake: https://www.snowflake.com/ Sridhar Ramaswamy: https://www.linkedin.com/in/sridhar-ramaswamy/ Stanford Graduate School of Business: https://www.gsb.stanford.edu/ Where to find Chris: LinkedIn: https://www.linkedin.com/in/chris-degnan/ 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 What is the job of a CRO? 01:12 What excellence looks like at different revenue stages 02:59 Sales leaders need to know how to sell the product 04:52 The hardest skill leaders have to learn 08:17 You need to stay open to feedback - at all levels 14:01 Sales, segmentation, and international expansion 16:17 Why MEDDIC is the foundation for every sales org 20:32 The metrics that actually matter 22:56 A week in the life of a CRO at scale 28:32 Navigating compensation at a GTM organization 31:45 What technical CEOs get wrong about GTM 36:01 The role of hunger in great sales leaders 40:35 What makes an exceptional IC sales rep 46:41 Dysfunctional vs. high-performing executive teams 48:01 Chris' most impactful decisions at Snowflake 49:53 "When there's doubt, there's no doubt" 54:49 Learning from world-class leaders

Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028. In today's episode, we discuss: Why early revenue hires fail What a top 1% CRO actually does The scaling mistake Stevie made by copying Twilio's playbook at Vanta Why Vanta remains 100% sales-led at every segment AI vs. humans in go-to-market References: Cursor: https://cursor.sh/ Gong: https://www.gong.io/ Salesforce: https://www.salesforce.com/ Twilio: https://www.twilio.com/ Vanta: https://www.vanta.com/ Where to find Stevie: LinkedIn: https://www.linkedin.com/in/steviecase/ 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 Why early revenue hires fail 02:23 Who to hire at $5M in revenue 04:16 Coin-operated sellers vs. long-term builders 05:57 What excellence looks like in the CRO role 07:44 Metrics, confidence, and velocity 12:04 Should CROs lead sales? 14:39 From shy seller to revenue leader 16:36 Learning to scale at Twilio 17:44 "There is no CRO playbook" 19:58 Stevie's scaling mistake at Vanta 22:16 Why Vanta stays 100% sales-led 23:16 The value of planning 24-26 months ahead 29:54 When trusting intuition was the wrong call 30:49 Do humans still have a place in the future of GTM? 33:33 Stevie's leadership non-negotiables 36:36 The myth of hiring for industry expertise 40:00 What stays centralized in a 600-person company 47:09 The hidden leverage of a customer's first 30 days 53:42 Why the CRO role will face enormous changes by 2028 58:42 What leaders must do now to stay relevant 01:02:30 Unpacking the CEO-CRO dynamic

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ 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 Intro 00:08 What design actually does at a software company 01:40 The roots of design: from industrial design to software 03:29 Useful, usable, desirable — and used 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 25:11 When lowering the quality bar actually cost the business 27:53 How to build judgment through pattern matching 31:25 How Ryan's design team differs from the rest 34:31 Why Figma is not the source of truth 36:32 How Ryan spends his week: recruiting, crits, and staff meetings 38:39 The "Do/Try/Consider" framework 42:12 The most important decisions of the past year 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution