All weeks

AI agents now drive 50% of Vercel's new business, up from 3% at the start of the year. Week of 5 October · 11 episodes

Manny Medina predicts normal software businesses will run on 40% gross margins, calling SaaS's 70-80% a cheap-money anomaly. Week of 28 September · 13 episodes Agentic usage drove Harvey's gross margin from roughly +50% to -50% within the first half of 2026. Week of 21 September · 5 episodes Keith Peiris says he no longer sees $10M–$15M Series A rounds getting done: investors either pass or put around $50M behind a $100B-outcome thesis. Week of 14 September · 4 episodes Mark Roberge says a truly AI-native sales team triples selling time, from 25% to 75% of the week. Week of 7 September · 6 episodes

Enterprise deals now close in about 45 days, making enterprise a better bet than mid-market, says Tomasz Tunguz. Week of 31 August · 5 episodes Justworks cut new-hire sales ramp from 18 months to 8. Week of 24 August · 6 episodes Warming territories before a rep starts cut ramp from a year and a half to 90 days. Week of 17 August · 4 episodes Top enterprise AEs now command $200,000 salary, $200,000 variable and up to $500,000 equity at sign-on. Week of 10 August · 5 episodes Tenable reps using AI as a co-pilot are freeing 15 to 25 percent of their week for customers. Week of 3 August · 5 episodes

Alan Chhabra says at least 50% of MongoDB's revenue went through a cloud marketplace, with 90% partner-touched. Week of 27 July · 5 episodes Backbase doubled its pipeline by running sales and marketing on an in-house AI system despite a 25% budget cut. Week of 20 July · 6 episodes Most churn is a sales problem, so Mark Roberge suggests paying reps half their commission at signature and half when customers hit the retention leading indicator. Week of 13 July · 6 episodes Katie Bullard says about 70% of the pattern-matching used to hire CROs, CFOs and CEOs is now obsolete. Week of 6 July · 4 episodes

Replit's CRO says over 90% of reps beat first-half quota, a sign the number was too low. Week of 29 June · 6 episodes AI could double sales rep productivity by lifting selling time from 30% to 60%, argues Mark Roberge. Week of 22 June · 4 episodes ClickUp's COO says AI lets engineers 100x themselves, but sellers may only get 2x to 5x. Week of 15 June · 6 episodes AI-native startups that hit $2-4M ARR quickly are now landing on acquirers' desks after retention failed. Week of 8 June · 3 episodes Yext's CEO sees very little evidence that AI-native companies are taking software spend from incumbents. Week of 1 June · 5 episodes

Referred customers are only about 20% of new customers but generate close to 80% of profitable growth. Week of 25 May · 4 episodes Endgame customers are cutting new-rep ramp from six months to two months, according to Alex Bilmes. Week of 18 May · 4 episodes A chief customer officer at a PE-backed company earns about 30% less than an equivalent CRO. Week of 11 May · 4 episodes Average outbound BDR output hit about $10K closed-won MRR last month, up from about $3.5K earlier, which Kyle Norton credits to AI. Week of 4 May · 5 episodes

Nearly 20% of traffic to Webflow customer sites now comes from AI crawlers, up from under 1%. Week of 27 April · 4 episodes Cursor's enterprise-led revenue went from $400,000 to almost $300 million in one year, outpacing its sales team. Week of 20 April · 4 episodes Cutting ICPs from about 30 to four took one company from $8M to $30M in three years. Week of 13 April · 3 episodes Roughly 70% of open pipeline sits outside the ideal customer profile, says Dan Sperring. Week of 6 April · 4 episodes

Replit's revenue went from about $2 million to $150 million in under a year, and it is pacing toward $1B. Week of 30 March · 4 episodes 1mind's AI agent sources 80% of its own pipeline, and its CEO says sellers won't exist. Week of 23 March · 5 episodes Intercom gave up about $60 million of contracted seat-based ARR to put the whole company behind Fin. Week of 16 March · 3 episodes Sierra hit $100 million ARR in seven quarters, then added $50 million more the next quarter. Week of 9 March · 5 episodes AI could replace up to 95% of go-to-market jobs within two to five years, 1mind's Amanda Kahlow predicts. Week of 2 March · 6 episodes

Investors now doubt the durability of AI revenue that reached $100M in under a year without renewals. Week of 23 February · 6 episodes The ten most notable US-listed SaaS companies lost upwards of $600 billion in market cap in six months. Week of 16 February · 4 episodes Gong put its category name in much bigger type than its own brand for two years. Week of 9 February · 5 episodes AI's first go-to-market win is lifting rep selling time from 25% to 80%, says Mark Roberge. Week of 2 February · 5 episodes

Pure outbound SDRs produce about six qualified opportunities a month, so they only pay above 40 to 50K ACV. Week of 26 January · 6 episodes Post-sales budgets should now be 7% of revenue, down from 10%, as AI enters customer-facing work. Week of 19 January · 4 episodes AI-native companies took 93% of Silicon Valley scale-up investment through Q3 2025, up from 23% in 2021. Week of 12 January · 4 episodes AI vendors face a 2026 retention reckoning as buyers who signed month to month cut back to a few tools. Week of 5 January · 3 episodes

Zapier raised about $1 million after Y Combinator and has never raised primary capital since. Week of 29 December · 1 episode