I advise CEOs, boards, and investors when technology is a key decision point — assessing and building the Product and Tech team, AI adoption, an M&A deal, or a platform that won't survive the next stage of growth.
Four ways I typically engage:
M&A & investment tech diligence
For: PE/VC firms and acquirers evaluating a target — or existing portfolio companies requiring evaluation. You get a clear-eyed perspective on architecture durability, team depth, security and privacy exposure, AI claims vs. AI reality. Delivered as a board-ready readout, not a 90-slide tech deep dive. I've sat on every side of this table — as operator, board director, and Qualified Technology Expert.
Fractional CPTO / technology leadership
For: Mid-market and PE/VC-backed companies between technology leaders, or whose current team needs senior air cover through a transition. Interim or fractional leadership of product and engineering: org design, roadmap ownership, hiring the permanent leader, and leaving the team stronger than I found it. At Chief I scaled product, design, and engineering from 8 to 110 through a $1.1B valuation; at Groupon I ran a 900+ person global org with a $100M+ OpEx budget; an Currciulum Associates I led the creation of a development center in Bangalore.
Product strategy & roadmap validation
For: CEOs and boards who need an independent answer to "is this roadmap real?" I pressure-test strategy against the market, the architecture, and the team's actual capacity — then align it with the P&L. Useful before fundraising, before a board vote, or when product and revenue have drifted apart. I delivered $25M in annualized savings at Groupon by making exactly these calls.
AI governance & readiness
For: Boards and executive teams deploying AI under real regulatory and reputational stakes. Practical governance that enables speed rather than blocking it: risk frameworks, privacy compliance (GDPR/CCPA/GLBA), vendor and model diligence, and board education. LLM in IT & Privacy; led AI platforms serving 17M+ students, where the compliance bar is unforgiving.
How engagements work
Most work is a focused 2–6 week diagnostic or an ongoing monthly advisory retainer. Diligence work runs on deal timelines. I take a small number of clients at a time so I can go deep.
Start a conversation: john@bits-not-atoms.com Prefer a quick session first? Book time on Intro
Also: I hold a small number of board director and board advisor seats. If you're building out technology expertise on your board, get in touch.