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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.
1:26:31EN
Lenny's PodcastPodcast · 2 speakersSelling in a Downturn: Bravado CEO Sahil Mansuri on Forecasts, Comp Plans, Retention and Warm IntrosGuest Sahil Mansuri · Host Lenny RachitskySahil Mansuri, founder of the sales community Bravado, lays out how B2B founders should change quotas, compensation, customer focus and deal-closing tactics when the market turns.
2:01:57ENLenny's PodcastPodcast · 2 speakersBuild the Sales Team Like a Founder: Jason Lemkin on Hiring, Comp and Keeping Product CloseGuest Jason Lemkin · Host Lenny RachitskySaaStr founder Jason Lemkin walks through when to hire your first reps, who to hire, how to pay them, how product and sales should work together, and why customer-hostile tactics don't compound.
1:01:41ENLenny's PodcastPodcast · 2 speakersDon't Outsource the Learning: Pete Kazanjy's Case for Founder-Led SalesGuest Pete Kazanjy · Host Lenny RachitskyThe author of Founding Sales explains why B2B founders should sell for a long time themselves, how to know when to hire, and how to get better at selling.
56:39ENLenny's PodcastPodcastDeals Don’t Die From Competition—They Die From IndecisionHost Lenny RachitskyMatt Dixon distills 2.5 million sales conversations into the JOLT method for frozen buyers and the Challenger lesson on teaching insight.Load moreShowing 24 of 26