I am a fractional Chief Product Officer. Every engagement, including a fractional role, starts the same way: six weeks, four days a week, before you commit a year and a budget to building the wrong thing. Some of them carry on from there.
Chief Product Officer four times · product, design and engineering as one organization · about 85 people at the largest
The sentences leadership teams say to me most.
Most of them are symptoms. The problem underneath usually goes by another name.
Every company I have worked in already had the information it needed. Not once did I turn up with a fact nobody had.
What was missing was the right name for the facts they already had. And a name is not a detail.
A name decides what you do next.
Seven things that were filed wrong, all of them mine. The short version first.
It arrives already named. And it is the document that decides what gets funded, who gets hired, and what the next year is about.
Six times a company has hired me, and six times the brief described something next to what was actually wrong. Not through carelessness. A brief describes the symptom, because the symptom is the part you can feel.
I am aware of how that sounds. A man whose living depends on you having misnamed something will tend to find that you have. So the work is built to end: six weeks, a fixed price, and a handover to your own people.
It is not the problem. It is the first thing to check.
If your brief is right, the fastest thing I can do is tell you so and leave.
Churn belonged to the support team. A number on a dashboard, in a row of other numbers, for about a year.
It was the ceiling on the entire company.
It was on the list of things to shut down. Almost no sales in ten months.
A thing you cannot sell alone can still be the reason two other things work. It became the brain, not the product.
Get new people to create a project. Every onboarding in the industry said so, including the one we had built.
Each new project made someone far less likely to pay. Creating project after project is not using a tool. It is shopping.
Hiring one meant a salary most of our customers could never afford.
Unless it is not a salary. Then it is a feature, and the people who were priced out have one.
A number we planned against, and held people to.
It is an output. You cannot forecast a number that gets set at the point of sale by somebody else.
A one-year curriculum. Students arrived, learned, left with a portfolio and hoped. It was already producing founders before I got there.
It was not a curriculum. It was a career incubator nobody had named, so nobody had engineered it. The teaching is the means. The outcome is the product.
I do not bring new facts.
I change what the facts are called.
And then the decision changes by itself, which is the part that makes it stick. Nobody has to be persuaded of anything. They look at the same thing under a different name and cannot un-see it.
Changing a name is half of it. The room has to use it.
You cannot tell someone their heading is wrong. Try it and watch them defend the heading, harder and for longer than they would defend the facts. So I don’t.
I ask the question that gets them there.
Then the new name is theirs. They argue for it in meetings I am not in. They are still using it after I have gone.
Some of that happens in a room. I run game design and trend workshops with leadership teams, because a future imagined cold comes back stale. At the design school I built a course that gave students seven weeks per nonprofit client to reach an idea that worked.
"He loves asking you difficult questions that force deep thought, but will make sure you feel empowered in solving them."
My job is the conditions: the tools, the training and the room to try. The careers are theirs. One person who wrote something similar now leads design at Asana. Another is an SVP of Product.
I incubated ideas that grew revenue and people who grew careers, and only one of those shows up in a P&L.
Public recommendations, so you can check them.
He has supported and contributed to all facets of our business: product development, marketing, branding, OKRs, business transformation, and people operations, along with managing and mentoring leaders in our organization. It is impressive how much Miles can help you across your entire organization.Rogayeh Tabrizi, PhD · Founder and CEO, Theory+Practice · 2024
Instrumental to helping us think more clearly and objectively, not only about our product roadmap but our business as a whole. High empathy for founder vision, but at the same time a pragmatist about what it takes to get products to market.Ali Davar · Chief Legal Officer, Owl.co · 2020
A talent for managing board conversations and securing support at the senior leadership level. He consistently builds bridges within organizations that struggle with sprawl and siloed thinking.Mya McDuffie · Director of Product Insights, Campminder · 2025
One thing. Better you know it before you call.
I take on hard rooms, turnarounds included. A frightened team does not put me off.
What I will not do is run a different plan from the one your board and your team believe in. Deciding how much a team can carry, and when, is part of the job. Letting them believe something that is no longer true is not.
Ambition is not the problem. If you want a round that takes risk off the table, or a sale at the right number, say so, and we will build a strategy that is honest about it.
A valuation target is not a strategy.
It is a
table.
Both of these assume there is time to think. If the building is on fire, you need decisions this week from someone in the seat. I do that too, and I will say so on the first call. There is one engagement behind both of these, and it is the same six weeks either way.
A platform bet, an acquisition, a new market. Funded, scheduled, and nobody around the table is arguing. Unanimity before a large irreversible decision is not usually agreement. It is usually that everyone is tired of the question.
I come in for six weeks, four days a week, with product, design and the commercial side as one job, and we find out whether the thing you are about to build is the thing you need.
A raise, a new market, a first acquisition. The next stage gets read by people whose job is to find the hole in the story, and they score you against benchmarks you may not have seen.
I have built that scorecard for my own companies. Better to find the hole yourselves, while it is still cheap to fix.
Against the year it protects.
What the read costs, against what it protects
Swipe the figure sideways
There is one question I will ask you first, and it is not a test:
What are you about to build, and who inside the company thinks it is a mistake?
There is no wrong answer. If the answer is nobody, that is the most useful thing either of us will learn in the first ten minutes.