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1:22:59ENDan Fougere on Building Datadog’s Sales Motion and Protecting PriceGast: Dan Fougere · Moderation: Harry StebbingsThe former Datadog CRO explains qualification, enterprise sales, discount discipline and the people behind a repeatable process.
1:23:01ENPhil Carter on Growth Loops and Consumer Subscription EconomicsGast: Phil Carter · Moderation: Harry StebbingsThe growth advisor explains acquisition, retention, paywalls and pricing, and why sustainable consumer subscriptions require more than buying traffic.
1:24:54ENJason Lemkin on SaaS Investing, Churn and Seed ValuationsGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder revisits successful and disappointing deals, explains his diligence process and assesses the economics of seed investing.
52:52ENGirish Mathrubootham on Freshworks Pricing, Products and ScalingGast: Girish Mathrubootham · Moderation: Harry StebbingsThe Freshworks founder shares lessons from self-service software, a multi-product strategy, executive hiring and investing in Indian startups.
1:03:31ENPeter Wagner on Venture Cycles, Founders and Price DisciplineGast: Peter Wagner · Moderation: Harry StebbingsThe Wing founding partner reflects on decades of investing, the Snowflake round he did not lead and the risks of capital-intensive businesses.
1:01:37ENDoug Adamic on Sales Discovery, Pipeline Quality and Why He Resists DiscountingGast: Doug Adamic · Moderation: Harry StebbingsThe Brex revenue leader explains how he connects customer outcomes to urgency, coaches sales teams and builds a repeatable process.







