Field Notes
How to Hire a Fractional CTO/CMO: Nine Questions Before You Sign
Five proposals went out on a system I built for a builder on the Cape. Four closed. The fifth did not come down to price. On that job the builder was asked to stop using the client portal, because it was embarrassing the architect. The tool outperformed the room badly enough to get switched off.
That is what an answer to "show me what you have produced" sounds like. A number with a denominator, a thing a client logged into, and a story with a loss in it. Most people offering a fractional seat cannot give you one. They can give you a deck.
If you are working out how to hire a fractional CMO, or a fractional CTO, or one person carrying both, the interview is nine questions. The answers tell you whether you are buying a seat accountable for the number or a retainer that borrowed the title.
What have you built, and can I log into it?
A straight answer names systems a client touches every day. A portal the homeowners open on Sunday night. A proposal system the bids actually go out on. A CRM with stages somebody fills in. Then it hands you a login, or points you at a page like the proof ledger and the working demos, where the thing itself is walkable.
A dodge is a PDF. Strategy documents, audit decks, a case study with a logo and no URL. Plenty of good advice has been sold that way, but advice is not what the seat is for. If nothing they built can be opened in a browser, you are interviewing a consultant with a new business card.
How are you paid, and what does "produced" mean in writing?
Straight: a low base, then a commission on the revenue the seat can prove it produced, under attribution rules both parties signed before the first week. The rules define a lead, name the pipeline stage where a deal becomes real, and list the channels that were already yours. Pipeline is sourced by the system. It is never "generated," because your estimating and your handshake close the job, and a fee schedule should say so.
Dodge: a flat monthly retainer with "fractional" printed on the invoice, which is an agency with fewer people. Or the reverse: a commission on revenue nobody can trace, which becomes an argument every quarter. If the tracking needed to define produced revenue does not exist yet, building it is the first job, and a candidate who says that out loud is telling the truth.
Who actually does the work?
Straight: one person, inside your business, on your calendar, and that person does the work. The volume comes from agent fleets doing the repetitive work, and that is how one seat covers what once needed a room. I wrote up how that shop runs. There is no bench behind it and nobody should imply one.
Dodge: "our team." "My people will handle onboarding." A named senior on the pitch and a junior on the account by month two. Ask who will be in the CRM at nine on a Tuesday. If what comes back is a department, you are hiring the agency you were trying to replace.
What do the first ninety days look like, in order?
Straight: systems first, because everything else stands on them. Site, a CRM with stages, the proposal system, the portal, and analytics that follow a click all the way to a signature. Then scale: search, follow-up automation, paid traffic only where the math closes on paper first. Then the compounding layer. Each stage has a done-when number, and the seat does not move up until that number reads true. The quarter-by-quarter version fits on a page.
Dodge: "it depends on the business." It does, a little, and a good operator still has an order. Ads in week one is the loudest dodge of all. It is the move that makes the report look busy while the bid at the bottom of the funnel still leaves as a PDF.
What would you cut on day one?
Straight: a line item, by name, and ideally one they could have sold you. The boosted posts. The second SEO vendor. The AI add-on tier on a platform that is billing for seats nobody logged into. Naming the cut costs the candidate something, which is exactly why it is worth hearing.
Dodge: "more budget." A seat that can only add spend is a seat with no brakes.
What will you refuse to do?
Straight answers here are a short list, and every item on it costs the operator money. No paid traffic until the CRM can name where each lead came from. No free checklist in front of the paid offer, because a free front door prices the seat before you have spoken. No redesign before the phone number is a link and the form lands in a pipeline. No number in a monthly report that cannot be traced to its source.
Dodge: nothing. They will do whatever you ask, which sounds like service and is actually the absence of judgment. You are paying for the no.
What happens when you leave?
Straight: nothing breaks. The systems were built in your accounts, on your domain, with your team trained to run them, and the handover was written into the build from the first day. A fractional seat is a rental of judgment, and the systems should outlast the rental.
Dodge: a proprietary platform. Exports available on request. A transition fee. Any answer where leaving costs more than staying is a lease with a penalty clause, and that is the oldest business model in this industry.
Show me the ledger.
Straight: numbers with a boundary attached. Mine, at Custom Crafted Homes on Cape Cod: $6.7M of qualified pipeline was actively working in the CRM, sourced by the systems, inside 75 days. Pipeline, not closed work. About $1.4M is closed, every dollar through that same CRM. The $1.1M home, closed off the rendered proposal, sits inside that closed figure, never on top of it. Two client portals are live. And the boundary rides with it: the systems were built here; the company closed the sales.
Dodge: a percentage with no denominator. A "closed" figure that turns out to be pipeline when you ask for the contracts. A ledger nobody will show you.
How many companies are you inside right now?
Straight: a small number, named honestly, with a plain yes or no about whether there is room for yours. One person can carry a few seats and do the work in each. The candidate who tells you they are full is more credible than the one who is never full.
Dodge: a count that does not fit inside one human being. Fourteen clients and "a team" is an agency. Fourteen clients and no team is a subscription to someone's attention, and you will get the leftovers.
Prove it on a build before you fill the seat
You do not have to decide any of this on an interview. Buy something small and watch it ship. For a builder, buy the Bid Room first: one bid at a fixed fee set by the size of the job — $5,000 on a $1M–$5M home — live within five business days of a complete intake, with no close fee on a job you brought. Send a real drawing and real numbers, and the packet that comes back is the interview. A portal works the same way. So does a migration. Fixed scope, a date, and a thing your people use once it lands.
No seat discussion until that has happened. It is the rule I hold myself to, and it is the reason the engagement ladder starts with a build instead of a conversation about titles. The seat itself, and what it does inside a building company, gets its own post: the fractional CTO/CMO for builders. If you are still weighing an agency against a hire against the seat, the comparison puts the three side by side.
Nine questions, one afternoon. Anyone worth hiring will enjoy answering them.