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1:12:06ENMax Freeman on Building Ramp’s Sales MachineGast: Max Freeman · Moderation: Harry StebbingsRamp’s sales leader explains how he hires, trains and equips sellers, from early outbound experiments to enterprise forecasting and AI-assisted research.
1:26:31ENSelling in a Downturn: Bravado CEO Sahil Mansuri on Forecasts, Comp Plans, Retention and Warm IntrosGast: Sahil Mansuri · Moderation: 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.
2:01:57ENBuild the Sales Team Like a Founder: Jason Lemkin on Hiring, Comp and Keeping Product CloseGast: Jason Lemkin · Moderation: 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.
1:01:41ENDon't Outsource the Learning: Pete Kazanjy's Case for Founder-Led SalesGast: Pete Kazanjy · Moderation: 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.
56:39ENDeals Don’t Die From Competition—They Die From IndecisionModeration: Lenny RachitskyMatt Dixon distills 2.5 million sales conversations into the JOLT method for frozen buyers and the Challenger lesson on teaching insight.
1:01:49ENFocus Wisely: How Calendly Grew from a Free Viral Tool into a Product-Led Business with a Sales TeamGast: Annie Pearl · Moderation: 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.
1:30:53ENObviously Awesome in Practice: April Dunford's Playbook for B2B Product PositioningGast: April Dunford · Moderation: 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.








