Ari Kaufman

Playbook

The AI Operator Playbook — Ari Kaufman

Ari Kaufman · 2026

The AI Operator
Playbook

How a PE-backed operating CEO turns the SaaS valuation crisis into a wealth creation engine using a systematic AI deployment model.

Years operating
PE-backed tech companies

Company exits
including a public IPO

PE CEO roles
lower & middle market

10x

Enterprise value increase
conservative case

The Deck

AriKaufman_AIOperatorPlaybook.pdf Download PDF

Download the deck Schedule 15 minutes

The Thesis in 30 Seconds

Rebuild From Within

Skunkworks audit identifies what AI can replace. Compress cost structure systematically while protecting revenue and client relationships.

Acquire & Compress

Buy revenue, not technology. Apply the same AI agent playbook to every acquisition. Revenue holds. EBITDA explodes.

Multiply the Multiple

Lower cost base on the same revenue rerates the exit valuation. Rinse and repeat across the portfolio.

Illustrative — $50M ARR Company

$5M

EBITDA entering
10% margin

$18.5M

EBITDA after
37% margin

$17.5M

Valuation before
3.5x EBITDA

$185M

Valuation after
10x EBITDA

Assumes 30% OpEx compression via AI agent deployment. Same revenue. Zero new customers required. This is the conservative case. Target companies: $25M to $100M+ ARR, PE-backed, lower and middle market.

Next Step

15 minutes is all it takes.

If a company in your portfolio is facing valuation compression, a leadership transition, or needs an operator who arrives with a specific plan, let’s talk.

Schedule a call

Track Record

CEO Placeable — PE-backed (United Communications Group), 3 acquisitions 5x investor return
CEO ThinkAcquisition — Bootstrapped to $100M in billings 10x investor return
CSO WILink [FTSE: WLK] — London Stock Exchange IPO, established platform for 4 acquisitions
GM LookSmart [NASDAQ: LOOK] — Grew paid search revenue $150M to $250M
CRO TruEffect — 300% revenue growth to $50M with Goldman Sachs support
Founder Zacks.com — First ad-supported financial website, $0 to $120M in four years