SaaS to AI Re-founding
You do not add AI to a SaaS company. You re-found the company around AI.
That means concentrating into the one workflow where AI replaces labor and the customer can measure the outcome. Then rebuilding pricing, commercial infrastructure, and operating cadence from that workflow out.
At iAdvize, 18 products became two: one vertical AI agent, and one SaaS add-on. AI quality improved first. Trial-to-paid conversion tripled in the first cohorts. Once we monetized, AI revenue went from $0 to $10M ARR in 24 months.
Re-founding is not transformation. It is a reset.
The pattern is visible at scale
Intercom is the clearest proof point. Eoghan McCabe returned as CEO, saw that conventional service software was going to be displaced by agents, and made the hard call to collapse the company around Fin. R&D shifted heavily toward Fin while it was still a small share of revenue. The company cut roughly $60M of ARR to reset pricing around outcomes. Mission, values, pricing, and operating focus changed with it. Fin then grew into a major business, with McCabe saying it was on track to pass $100M ARR.
McCabe understood which part of Intercom was durable and which part was not.
Know which part of your company is QWERTY and which part is the carriage
QWERTY survived every transition since 1873: typewriter, computer, phone, tablet. The carriage moved the typewriter across the page. Essential to the machine. Then the machine changed.
A lot of the 20-year SaaS playbook is carriage: build a CRUD app for a persona, market it, sell it, implement it, renew it. That motion built great companies. It is not the part that survives.
Your QWERTY is the durable asset: clarity on the job to be done, proprietary data, workflow depth, the operational task the AI must execute. Everything else is carriage.
How it works
- 01
Identify your QWERTY.
- 02
Rebuild the core workflow with AI as the execution layer, not an assistant. The product is now the outcome, not a UI screen.
- 03
Set the unit: Customer EBITDA Created.
- 04
Design the commercial motion: deliver first, monetize, and expand margins.
- 05
Reset the organization around AI performance: quality, trial-to-paid conversion, Customer EBITDA Created, WoW improvement. Not quarterly.
Key takeaway
Do not get sentimental about the carriage. The companies that treat AI as a feature addition will be outcompeted by those that re-found from the outcome and rebuild the workflow. QWERTY is what survives when the machine changes.
If AI is real inside the company but still not showing up in EBITDA, the company has not re-founded yet.
If your portfolio company has AI that isn't driving EBITDA, I've solved that problem twice.