The CTO Seat
I plug in as the senior technical voice in the room — the one founders, investors, and engineers all defer to on direction. 1–2 days a week, accountable for outcomes, not hours. That includes the moments that decide whether the company survives to the next stage: closing the round, hiring the first five engineers, and standing behind the technical story when someone else's due diligence tests it.
The Second Opinion
- The verdict on the decision you named at booking: sign, renegotiate, stop, or move the date
- Whether the date you have been given is real, and what actually drives it
- What it will cost to finish — the number, not a range with an asterisk
- Whether the rewrite you have been offered is necessary or convenient
- Whether the people building it are the right people to finish it
- Where the key-person risk sits, and what happens if that person resigns on Friday
- The next decisions ranked by when they fall due — this week, this month, this quarter
- A named owner for checking the verdict gets done. If that owner is a hire and not me, the report says so
- Included: the contract read — the contract, quote or offer on the table read against the IP, exit, acceptance and payment clauses before day one, returned as plain-English notes for your lawyer
- Included: run the next one without me — the questions to ask on every status update for the next 90 days, so the next date can be checked in-house
- Included: the date call — thirty minutes on or just before your date, re-reading the verdict against what actually happened
If it doesn't give you a decision you can act on before your date, you don't pay for it.
The report ends by naming who checks it gets done. Sometimes that is a hire, and the report says which one. Sometimes it is the seat — and that is the only way the seat is offered.
- Set architectural direction and 6–12 month technical roadmap
- Own build-vs-buy calls and platform-level trade-offs
- Unblock engineering on the hard calls so the team doesn't stall
- Technical counterparty on investor and board calls
- Quarterly board updates tied to engineering outcomes
- Honest read on the team, the stack, and the runway implications
- Technical DD pack, cap table modelling, and SeedLegals/term-sheet review run alongside the retainer
- Bottom-up runway model and use-of-funds narrative aligned to the round
- Investor-ready data room, kept current rather than assembled the week before a raise
- Role design, interview loops, and calibration for the first five engineering hires
- Engineering ladder, levelling, and comp bands benchmarked against UK/EU market
- Pre-investment or pre-acquisition technical DD: codebase, architecture, security, and team review — 5–7 days, IC-ready report
- Weekly 1:1s with engineering leads
- Calibrate hiring bar, performance, and comp bands
- Run incident response and post-mortems when they matter
Full-time search vs a fractional CTO
The ranges below are what each path typically takes. A fractional CTO compresses them because there's no search process to run first, and fundraising, hiring, and diligence are workstreams on day one rather than a mandate you build up to.
No search process to run first — I start on the roadmap, the board pack, and the open hires in week one, not after a quarter of interviewing.
They run alongside the technical roadmap from day one, rather than a separate engagement spun up from a standing start when the round or the hiring plan suddenly becomes urgent.
Having built and reviewed data rooms, cap tables, and DD packs before means the report and the narrative don't start from a blank page.
Ranges assume a single technical hire covering this scope. A search for a VP Engineering plus a separate fundraising advisor plus a separate DD firm takes materially longer to assemble than either path above.
A contract to sign, a quote to accept, or a date you didn't set — a short call is enough to know if the review lands before it.
- 12-month technical roadmap with tied milestones
- Quarterly board pack (technical section)
- Architecture decision records (ADRs) for the load-bearing calls
- Investor-ready data room, financial model, and technical DD pack when fundraising
- Hiring plan, interview kit, and engineering ladder when building the team
- A monthly statement of what engineering cost you and what it bought — written so you can hand it to your board without translating it first
Ongoing retainer, 1–2 days per week. Most seats open with The Second Opinion, then run on 30-day rolling notice. Everything lives in your own accounts and repos: I hold the seat, not the keys.
If it doesn't give you a decision you can act on before your date, you don't pay for it.
You book the review against a decision and a date. The report exists to put a verdict in your hands before that date — sign, renegotiate, stop, or move it. If it lands late, or lands without a verdict you can act on, the fee is waived.
- The decision and the date are written down at booking. That is what the report is measured against.
- Five working days run from the day the access we agreed is granted, and must finish before your date — if they can't, I say so before you book, not after.
- Waived on written notice within 14 days of the report, or before your date, whichever comes first.
- No build proposal appears in the report. The report is yours to take to anyone.
- If the review concludes you do not need a CTO seat, it says so and the seat is not offered.
- Excludes the investor due-diligence edition — that decision belongs to the investor, not to me.
Questions I get asked about this.
Do you run fundraising support as part of the retainer, or is it separate?
Part of the retainer if I'm already your CTO — it's the same accountability, just pointed at a round instead of a roadmap for a few weeks. If you need fundraising support without an ongoing CTO relationship, it runs project-shaped instead: 6–12 weeks from kickoff to close.
Can I get technical due diligence without a retainer?
Yes. It runs standalone, fixed-fee, with a 5–7 day turnaround: codebase, architecture, security posture, and team review, written up for an investment committee. Common before an acquisition, an investment, or when you've inherited a codebase and need an honest read on it.
What if I already have a Head of Engineering?
Then I sit above or alongside them, depending on what's missing — usually board-level technical accountability, architecture ownership, or a second opinion on the hard calls. I'm not there to replace a working reporting line, only to fill the gap above it.
Do I have to take the seat after the review?
No, and the review is written on the assumption that you might not. "You don't need a CTO yet, you need this specific hire" is one of the verdicts I write, and I have written it. The report is yours either way — including to take to someone else.
How fast can you actually start?
Typically within one to two weeks of the discovery call. Seats open with The Second Opinion — five working days against the date you bring — so we both know it's the right fit before anything ongoing is agreed.
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A build you can't evaluate, a demo that has to ship, or a certificate a contract is waiting on.
Book a 30-minute discovery call. If we're not a fit, I'll tell you on the call — and point you toward someone who is.