Results
Two operational restructures. The AI worked before the commercial model did.
iAdvize
$0 to $10M+ AI ARR in 24 months. Collapsed 18 products into two: one vertical AI agent, one SaaS add-on, deployed inside a B2B vertical SaaS platform. Sales cycles compressed from 9 months to 60 days. Trial-to-paid conversion tripled in Year 1. AI ARR overtook legacy SaaS revenue within the hold period. Enterprise customers included Otterbox, Kendra Scott, LG.com, Microsoft, Airbnb, SAP, and AT&T.
$0→$10M
AI ARR
18→2
Product reset
9mo→60d
Sales cycle
3x
Trial-to-paid
Consumption
Pricing model
AI-first
GTM rebuilt
Directly
Promoted to CEO when obligations exceeded cash. Rebuilt cost architecture and deployed AI automation contributing an estimated 50% of EBITDA at exit. Negative to 22% in 12 months, 31% at close. Led the complete exit process as CEO, from advisor selection through diligence, negotiation, and board coordination. Asset sale to a PE-backed acquirer.
34%→43%
Net revenue capture
22%
EBITDA margin
est. 50%
EBITDA at exit
PE exit
Asset sale
Outcome
Per-resolution pricing
PE-backed
Acquirer
Principles
- 01
The AI transition is a re-founding, not an upgrade.
- 02
The bottleneck is commercial infrastructure that converts AI into revenue quality.
- 03
Outcome pricing is the destination. Usage pricing is the bridge.
- 04
The renewal is the new sale. AI only renews when it moves a line on the customer’s P&L.
- 05
Durable EBITDA comes from aligning price to value.
The frameworks behind these results
Working AI that isn't converting to EBITDA is the exact reset I've run. Email me if you're living it too, and I'll send back the reset on one page.