Sunday, 31 May 2026

The Briefing

CAC payback of 32 months in the $5M–$50M ARR band signals inefficiency that would have drawn alarm in 2021 but now reflects a deliberate recalibration toward durability over blitz-scaling. This briefing examines that shift through Q1 private company benchmarks, where the tension between growth velocity and unit economics remains unresolved, alongside Kellogg's emerging framework for measuring software durability and a technical deep-dive into agentic security systems—a category where AI promises to collapse mean-time-to-response but threatens to expand the attack surface simultaneously. The through-line: capital efficiency is no longer optional theater for Series B decks; it's table stakes. Watch whether payback periods compress in Q2 or whether founders continue trading speed for margin expansion.

Today's Number

CAC Payback Period

32

SIM–SSM ARR band

Active DebateAI in Finance

KeyBanc vs OnlyCFO

Claim 6 shows nearly all SaaS companies expect to invest in AI with anticipated operational impacts, while claim 9 indicates over 50% of finance leaders lack an AI strategy, suggesting investment intention without strategic clarity.

Nearly all SaaS companies in the survey expect to invest in AI in 2025, with impacts to business operations anticipated within the next 3 years
— KeyBanc Capital Markets & Sapphire Ventures 2025 SaaS Survey: AI-Driven Growth & Profitability Focus
Over 50% of finance leaders have no AI strategy for adopting AI into finance and accounting
— How to AI (CFO Edition): AI Adoption Strategy and Finance Use Cases
Rising Author

Dave Kellogg

3 new articles in the last 60 days · up 90% vs prior 60d · 207 all-time

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Fresh BenchmarkTomasz Tunguz (Theory Ventures)

AI-Powered Security: Building Agentic Defense Systems for the Enterprise

This article discusses the emerging challenge of securing enterprises where both attackers and defenders operate as autonomous AI agents. Featuring CISO Jonatha

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