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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.
1:26:31EN
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.
1:01:49ENLenny's PodcastPodcast · 2 speakersFocus Wisely: How Calendly Grew from a Free Viral Tool into a Product-Led Business with a Sales TeamGuest Annie Pearl · Host Lenny RachitskyCalendly's chief product officer Annie Pearl explains how the company picks its customers, plans its roadmap, and layers sales on top of product-led growth.
1:30:53ENLenny's PodcastPodcast · 2 speakersObviously Awesome in Practice: April Dunford's Playbook for B2B Product PositioningGuest April Dunford · Host Lenny RachitskyThe author of Obviously Awesome explains how to tell whether positioning is broken, how to rebuild it step by step, and why one persona matters more than the rest.