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20VC with Harry Stebbings· May 7, 2026Podcast · 3 speakersAI Spending, Software Stocks and IPO Speculation: A 20VC Earnings RoundtableGuest Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsJason Lemkin and Rory O’Driscoll assess technology earnings, software growth and reported AI funding, then debate how leaders and workers adapt to AI.
45:35EN20VC with Harry Stebbings· Dec 2, 2024Podcast · 2 speakersNik Storonsky on Revolut’s Product Bets and Global Banking AmbitionsGuest Nik Storonsky · Host Harry StebbingsThe Revolut founder discusses management, banking licenses, product experiments and a possible public listing, as well as his data-driven investment firm.
53:03EN20VC with Harry Stebbings· Oct 4, 2024Podcast · 2 speakersMaria Angelidou-Smith on Product Reviews, Hiring and Building Better TeamsGuest Maria Angelidou-Smith · Host Harry StebbingsThe Personio product and technology leader shares lessons from Meta on product careers, decision-making, resource allocation and leading distributed teams.
1:02:58EN20VC with Harry Stebbings· May 10, 2024Podcast · 2 speakersLarry Shurtz on Hiring Sales Teams, Vertical Playbooks and ForecastingGuest Larry Shurtz · Host Harry StebbingsThe Genesys sales leader explains how to prioritize, onboard and coach sellers, and why industry expertise must extend beyond the account executive.
1:05:46EN20VC with Harry Stebbings· Mar 29, 2024Podcast · 2 speakersBilly Hult on Tradeweb, Leadership and Betting on PeopleGuest Billy Hult · Host Harry StebbingsTradeweb’s CEO discusses the transition to leadership, how he weighs talent and feedback, and the personal cost of a demanding role.
48:02EN20VC with Harry Stebbings· Mar 8, 2024Podcast · 2 speakersBrendon Cassidy on Early Sales Hiring, Discovery and OutboundGuest Brendon Cassidy · Host Harry StebbingsThe sales leader explains how he evaluates first hires, builds a customer-centered playbook and reviews deals, while questioning conventional outbound tactics.
1:29:20EN20VC with Harry Stebbings· Feb 26, 2024Podcast · 2 speakersJustin Ishbia on Private Equity, Building Teams and the Benefits of ScaleGuest Justin Ishbia · Host Harry StebbingsThe Shore Capital founder explains his buyout strategy, how he develops leaders and why he treats operations as a system.
59:25EN20VC with Harry Stebbings· Feb 21, 2024Podcast · 2 speakersScott Williamson on Hiring Product Managers and Writing Better StrategyGuest Scott Williamson · Host Harry StebbingsThe former GitLab product leader explains his hiring process, written strategy tools and routines for coaching and reviewing product work.
1:12:20EN20VC with Harry Stebbings· Jan 31, 2024Podcast · 2 speakersDave Kellogg on SaaS Metrics, Sales Forecasting and Efficient GrowthGuest Dave Kellogg · Host Harry StebbingsThe software executive explains why he separates acquisition, retention and margin, and offers practical ways to improve forecasting and customer relationships.
35:04EN20VC with Harry Stebbings· Jan 26, 2024Podcast · 2 speakersDave Ripley on Crypto Regulation, Payments and Leading KrakenGuest Dave Ripley · Host Harry StebbingsThe Kraken CEO makes the case for cryptocurrency and a different regulatory approach, while Harry Stebbings challenges its practical advantages.
1:13:51EN20VC with Harry Stebbings· Jan 24, 2024Podcast · 2 speakersSean Murray on Teaching Buyers and Moving into Enterprise SalesGuest Sean Murray · Host Harry StebbingsThe Greenhouse revenue leader explains how he approaches discovery, renewals, enterprise readiness and sales hiring.
1:10:01EN20VC with Harry Stebbings· Dec 22, 2023Podcast · 2 speakersDave Powers on Building Hoka, Reviving UGG and Managing Footwear BrandsGuest Dave Powers · Host Harry StebbingsThe Deckers CEO discusses specialist distribution, inventory, brand recovery and the economics of direct and wholesale sales.
55:24EN20VC with Harry Stebbings· Dec 13, 2023Podcast · 2 speakersSteve Goldberg on Selling to CFOs, Reviewing Deals and Building Customer TrustGuest Steve Goldberg · Host Harry StebbingsThe Salesloft revenue leader explains how to find a real champion, demonstrate business outcomes and make renewals part of the sales process.
1:53:24EN20VC with Harry Stebbings· Nov 20, 2023Podcast · 2 speakersMatteo Franceschetti on Eight Sleep’s Hiring, Execution and Sleep TechnologyGuest Matteo Franceschetti · Host Harry StebbingsThe Eight Sleep CEO explains the operating decisions behind a hardware startup, from unit economics and hiring to written management and ambitious health-monitoring plans.
1:03:08EN20VC with Harry Stebbings· Nov 13, 2023Podcast · 2 speakersRyan Petersen on Flexport, Velocity and the Cost of Moving Too FastGuest Ryan Petersen · Host Harry StebbingsThe Flexport founder discusses customer feedback, overhiring, cross-functional logistics and why direction matters as much as speed.
57:34EN20VC with Harry Stebbings· Nov 10, 2023Podcast · 2 speakersChris Degnan on Building Snowflake's Sales Team from the First CustomerGuest Chris Degnan · Host Harry StebbingsSnowflake's revenue chief explains prospecting, customer feedback, forecasting and his unconventional view of customer success.
1:05:26EN20VC with Harry Stebbings· Jul 28, 2023Podcast · 2 speakersStephane Kurgan on Scaling King, Making Decisions and Building TrustGuest Stephane Kurgan · Host Harry StebbingsThe former King COO explains how he approaches data, communication, hiring and the difficult choices that come with rapid growth.
1:07:44EN20VC with Harry Stebbings· Jul 26, 2023Podcast · 2 speakersSri Batchu on Growth Experiments, Hiring and Operator InvestingGuest Sri Batchu · Host Harry StebbingsThe Ramp growth leader explains how to measure experiments, build teams and balance operating with angel investing.
1:00:38EN20VC with Harry Stebbings· Jul 17, 2023Podcast · 2 speakersDave Clark on Amazon, Flexport and Leading Through GrowthGuest Dave Clark · Host Harry StebbingsThe former Amazon executive discusses ambitious goals, hiring, logistics decisions and protecting time for family.
1:04:31EN20VC with Harry Stebbings· Jul 10, 2023Podcast · 2 speakersSimon Sinek on Trust, Listening and the Work of Being a Better LeaderGuest Simon Sinek · Host Harry StebbingsThe author discusses identity, difficult conversations and how leaders can create space for honest feedback and productive dissent.
1:05:33EN20VC with Harry Stebbings· Jun 7, 2023Podcast · 2 speakersRich Liu on Sales Hiring, Enterprise Growth and Deal DisciplineGuest Rich Liu · Host Harry StebbingsEverlaw’s revenue leader shares practical lessons on selling in a tighter market, building a team and choosing a go-to-market motion.
59:06EN20VC with Harry Stebbings· Apr 19, 2023Podcast · 2 speakersMark Goldberger on Enterprise Sales, Hiring and Deal QualificationGuest Mark Goldberger · Host Harry StebbingsRamp’s enterprise sales leader discusses founder-led selling, champions, onboarding and building a disciplined pipeline.
1:01:46EN20VC with Harry Stebbings· Mar 22, 2023Podcast · 2 speakersFrank Fillmann on Enterprise Sales, Hiring and Customer-Centered PlaybooksGuest Frank Fillmann · Host Harry StebbingsThe Salesforce sales leader explains how he coaches teams, maps opportunities and builds a case around the buyer’s priorities.
53:16EN20VC with Harry Stebbings· Jan 6, 2023Podcast · 2 speakersJason Fried on Independence, Leadership and Basecamp’s Workplace DecisionsGuest Jason Fried · Host Harry StebbingsThe 37signals co-founder discusses profitability, feedback and long partnerships, and reflects on a controversial workplace policy.Load moreShowing 24 of 30