In Depth

What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)

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

The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)

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

Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)

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

Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)

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

Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)

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