The people who build engineering organizations, assessing them for you.
We pair enterprise AI strategy with technology due diligence. For operators, that turns AI from a slide into shipped capability. For investors, it is a clear-eyed read on the product, the architecture, and the team behind a deal.
Updated 8 July 2026
The thesis
Most technology advice is written by people who left the arena years ago. Ours is written by people still in it, running an AI-native group of operating companies, shipping products every week, and living with the consequences of every architectural call.
That is the whole difference. When we tell an enterprise where to place its AI bets, it is because we are placing the same bets ourselves. When we tell an investor a codebase will not survive its next scale phase, it is because we have carried teams through exactly that wall. Judgment earned in production travels. A generic maturity framework does not.
What we do
- 01 For operators
AI strategy & digital transformation
We start from the business, not the model. A sequenced roadmap your teams can execute, and the delivery discipline to keep it moving from demo to production.
- 02 For operators
Engineering organization design
Team topology, hiring, and delivery practice shaped so the org compounds instead of clogs. The playbook that ran 500-plus engineers at Adidas, adapted to your stage.
- 03 For investors
Technical due diligence
Product, architecture, and team assessed against the thesis and the price. A decision-ready read on the risks that move the deal, fast enough for a live process.
- 04 On call
Fractional CTAIO leadership
Operator-level technology judgment in the room when you need it, without a full-time hire. Board prep, a critical build, a turnaround. Accountable to the outcome.
Who we help
Enterprises betting on AI
You know AI reshapes your category. You need it to become shipped capability with measurable return, not a proof-of-concept graveyard. We bring the strategy and the execution discipline to get there.
PE, VC & founders
You are pricing a deal or defending a thesis. You need to know whether the technology and the team can carry the plan. We give you a clear, decision-ready read, fast enough for a live process.
Selected clients
“Advice earned in production travels. A template does not.”
Press & recognition
HotTopics Global CIO 2026 Thomas Prommer · Group CEO Read → 
Fast Company World Changing Idea 2026 Flywheel Motion Read → In the press
- Why most companies still think too small about AI
- State of the CIO, 2026: CIOs set the course for AI ROI
- Enterprises still chase incremental, not transformational, AI gains
As featured in
- HotTopics
- Fast Company
- AP News
- USA Today
- CIO.com
- Barchart
Common questions
What does Flywheel Advisory actually do?
Two things that reinforce each other: we help enterprises design and execute AI strategy and digital transformation, and we run technology due diligence for private equity firms, venture investors, and founders. The same people who build and run engineering organizations are the ones who assess them for investors.
Who leads the engagements?
Thomas Prommer, our Group CEO and CTAIO, leads advisory personally. He was Global SVP of Engineering at Adidas (500+ engineers), CIO at Sweetgreen, and Senior Technology Advisor at Bain Capital. You get operator judgment, not a slide deck from someone who has never shipped.
How is technical due diligence different from a consulting audit?
Due diligence is written for a decision: invest, walk, or renegotiate. We assess the product, the architecture, and the team against the thesis and the price, then hand you a clear read on the risks that actually move the deal, not a generic maturity score.
Do you only work with large enterprises?
No. Enterprises come to us for transformation; investors and founders come to us for validation. Engagements scale from a focused two-week diligence sprint to a multi-quarter transformation program.
Start here
Tell us the decision you're facing.
A build to get right, a transformation to sequence, or a deal to de-risk.
Get in touch