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1:12:06EN
20VC with Harry Stebbings· Oct 10, 2026Podcast · 2 speakersMax Freeman on Building Ramp’s Sales MachineGuest Max Freeman · Host Harry StebbingsRamp’s sales leader explains how he hires, trains and equips sellers, from early outbound experiments to enterprise forecasting and AI-assisted research.
1:23:34EN20VC with Harry Stebbings· May 23, 2026Podcast · 3 speakers20VC on Enterprise Sales Hiring, Compensation and AIGuest Chad Peets, Chris Degnan · Host Harry StebbingsChad Peets and Chris Degnan discuss building sales teams, forecasting revenue and competing for talent while AI changes enterprise markets.
1:13:48EN20VC with Harry Stebbings· May 11, 2026Podcast · 2 speakersPatrick Forquer on Selling Legal AI and Scaling Legora’s Revenue TeamGuest Patrick Forquer · Host Harry StebbingsLegora’s chief revenue officer explains how his team runs pilots, trains salespeople and forecasts rapid growth, and shares company-reported performance figures.
1:14:23EN20VC with Harry Stebbings· May 2, 2026Podcast · 2 speakersBecca Lindquist on Clay’s Sales Hiring, Compensation and AIGuest Becca Lindquist · Host Harry StebbingsClay’s head of sales explains how she evaluates candidates, designs incentives and builds customer champions in a product-led business.
1:25:37EN20VC with Harry Stebbings· Apr 11, 2026Podcast · 2 speakersCarles Reina on ElevenLabs Sales, Compensation and Global GrowthGuest Carles Reina · Host Harry StebbingsThe ElevenLabs sales leader explains his approach to quotas, AI-assisted workflows, international markets and partner distribution.
1:05:06EN20VC with Harry Stebbings· Mar 21, 2026Podcast · 2 speakersShaunt Voskanian on Figma’s Sales Motion, Quotas and CoachingGuest Shaunt Voskanian · Host Harry StebbingsFigma’s chief revenue officer explains how self-service adoption connects to enterprise sales, and why quota targets are only one part of evaluating a representative.
54:12EN20VC with Harry Stebbings· Mar 7, 2025Podcast · 2 speakersJulian Teixeira on Hiring Sales Teams and Building a Repeatable ProcessGuest Julian Teixeira · Host Harry StebbingsThe 1Password CRO discusses early hires, team goals, outbound prospecting, compensation and inspecting deals as a company scales.
1:12:04EN20VC with Harry Stebbings· Jan 24, 2025Podcast · 2 speakersCarlos Delatorre on Hiring Salespeople and Building a Repeatable PipelineGuest Carlos Delatorre · Host Harry StebbingsThe Harness CRO explains why account executives should prospect, how he structures a weekly pipeline routine, and how sales leaders can train and evaluate their teams.
1:10:55EN20VC with Harry Stebbings· Dec 20, 2024Podcast · 2 speakersMatt Plank on Building Rippling’s Sales Organization and Scaling OutboundGuest Matt Plank · Host Harry StebbingsThe Rippling CRO explains how his team plans capacity, works with marketing, prices deals and adapts its sales model as the product portfolio grows.
1:13:42EN20VC with Harry Stebbings· Dec 13, 2024Podcast · 2 speakersGuillaume Moubeche on Bootstrapping lemlist Through Sales and ContentGuest Guillaume Moubeche · Host Harry StebbingsThe lempire founder describes the early sales work, product mistakes and content strategy behind a bootstrapped software business.
1:14:15EN20VC with Harry Stebbings· Dec 6, 2024Podcast · 2 speakersZachary Bookman on OpenGov, Venture Capital and a $1.8 Billion SaleGuest Zachary Bookman · Host Harry StebbingsThe OpenGov CEO discusses enterprise sales, founder–investor incentives, acquisitions and the long path to liquidity.
1:22:59EN20VC with Harry Stebbings· Nov 22, 2024Podcast · 2 speakersDan Fougere on Building Datadog’s Sales Motion and Protecting PriceGuest Dan Fougere · Host Harry StebbingsThe former Datadog CRO explains qualification, enterprise sales, discount discipline and the people behind a repeatable process.
1:08:51EN20VC with Harry Stebbings· Oct 23, 2024Podcast · 2 speakersAJ Tennant on Enterprise Sales, Customer Success and HiringGuest AJ Tennant · Host Harry StebbingsGlean’s sales leader explains how to move upmarket, make AI deployments successful and evaluate sales candidates.
1:00:46EN20VC with Harry Stebbings· Sep 27, 2024Podcast · 2 speakersJeetu Mahtani on International Expansion, Sales and Customer SuccessGuest Jeetu Mahtani · Host Harry StebbingsThe former HubSpot sales leader explains how to test a new market, build partner ecosystems and align sales incentives with customer outcomes.
1:11:51EN20VC with Harry Stebbings· Sep 11, 2024Podcast · 2 speakersDavid Schneider on Scaling ServiceNow and Being a Useful InvestorGuest David Schneider · Host Harry StebbingsThe former ServiceNow operator discusses enterprise sales, multi-product growth and board work, including the decisions he would make differently.
1:07:53EN20VC with Harry Stebbings· Aug 23, 2024Podcast · 2 speakersChad Peets on Building Sales Teams, Hiring and Product CollaborationGuest Chad Peets · Host Harry StebbingsThe sales recruiter and investor discusses early customer discovery, sales economics, onboarding and the trade-offs of scaling a team.
58:31EN20VC with Harry Stebbings· Aug 2, 2024Podcast · 2 speakersBen Fiechtner on Deal Design, Forecasting and Building Sales TeamsGuest Ben Fiechtner · Host Harry StebbingsClari’s chief revenue officer explains his quarterly sales cadence, how to find real buying constraints, and what he looks for when hiring.
45:11EN20VC with Harry Stebbings· Jul 12, 2024Podcast · 2 speakersMark Roberge on Sales Hiring, Unit Economics and Moving UpmarketGuest Mark Roberge · Host Harry StebbingsThe former HubSpot sales leader explains how founders can build a sales motion, align incentives and decide when enterprise customers are worth pursuing.
54:43EN20VC with Harry Stebbings· Jul 10, 2024Podcast · 2 speakersAra Mahdessian on ServiceTitan’s Customer Focus and LeadershipGuest Ara Mahdessian · Host Harry StebbingsThe ServiceTitan CEO discusses early financing, moving upmarket, pricing and how he tries to inspire a demanding team.
53:43EN20VC with Harry Stebbings· Jun 7, 2024Podcast · 2 speakersAshley Kelly on Hiring, Onboarding and Scaling Sales DevelopmentGuest Ashley Kelly · Host Harry StebbingsRippling’s sales-development leader discusses SDR roles, compensation, coaching and the practical challenges of growing a global team.
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.
1:15:57EN20VC with Harry Stebbings· Apr 12, 2024Podcast · 2 speakersSam Blond on Hiring Sales Teams and Making Outbound WorkGuest Sam Blond · Host Harry StebbingsThe former Brex sales leader explains how founders can hire early reps, diagnose demand bottlenecks and build more distinctive outreach.
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.
1:11:02EN20VC with Harry Stebbings· Feb 14, 2024Podcast · 2 speakersMartin Gontovnikas on Product-Led Growth and Selling to EnterprisesGuest Martin Gontovnikas · Host Harry StebbingsThe former Auth0 growth leader explains how to connect user adoption to enterprise sales, learn from failed experiments and protect the product experience.Load moreShowing 24 of 36