cloudedjudgement.substack.com · 2026-02-27 · 97d

Clouded Judgement: The Poison of Inertia

The article analyzes Block's 40% headcount reduction as a symptom of organizational inertia during major technological shifts, drawing parallels to how incumbents like Sabre failed to capitalize on the internet transition. The author argues that large SaaS companies must forcefully restructure to compete in an AI-driven world where new operational playbooks and cost structures are required.

15 metrics· Cited 0× in the knowledge base ·Open source ↗

Metrics in this report

CAC Payback Period

34months

median

SaaS public companies

Enterprise Value / NTM Revenue Multiple

3.3multiple

median

Overall SaaS market

Enterprise Value / NTM Revenue Multiple

16.6multiple

median

Top 5 SaaS companies

Enterprise Value / NTM Revenue Multiple

10.3multiple

median

High growth SaaS (>22% NTM growth)

Enterprise Value / NTM Revenue Multiple

6.3multiple

median

Mid growth SaaS (15-22% NTM growth)

Enterprise Value / NTM Revenue Multiple

2.6multiple

median

Low growth SaaS (<15% NTM growth)

FCF Margin

20percent

median

SaaS public companies

G&A as % of Revenue

15percent

median

SaaS public companies

Gross Margin

76percent

median

SaaS public companies

LTM Growth Rate

15percent

median

SaaS public companies

NTM Growth Rate

12percent

median

SaaS public companies

Net Dollar Retention

109percent

median

SaaS public companies

Operating Margin

-1percent

median

SaaS public companies

R&D as % of Revenue

24percent

median

SaaS public companies

Sales & Marketing as % of Revenue

35percent

median

SaaS public companies