You have a thesis, and a company that is not behaving the way the thesis said it would. I read the plan, the product, the people and the incentives together, and tell you what the problem is actually called.
Chief Product Officer four times · inside companies like the ones you buy
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The brief usually arrives as a technical audit: the stack was never integrated, so find out what it will cost to fix.
Sometimes that is the answer. More often, a year after a deal, something is wrong with the thesis, and the stack is just where it shows.
The sentences investors and operating partners say to me most.
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The four places a thesis usually breaks.
Whether the people you have can deliver the plan you underwrote, and whether the gap is capability, structure or a person. It is a person less often than the brief assumes.
What the company actually sells, what everything else depends on, and what to stop paying for.
How the structure of the deal lands on the people doing the work. A deal can take the urgency out of a team without anyone deciding to.
Who is right for the next stage, who is right for a different seat, and what support nobody has been given yet.
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The read includes the CEO, and I say so on the first day. That part is never a line in a report. It happens one to one, in a few coaching sessions inside the six weeks, because how a chief executive sees their own effect on the company often shapes the culture more than anything else. Nothing anyone tells me is attributed. I ask for their plan before I share mine.
The team will be nervous anyway. How the first week runs decides whether people tell me the truth, so I run it myself.
Public LinkedIn recommendations, so you can check them.
Miles has been instrumental to helping us think more clearly and objectively, not only about our product roadmap but our business as a whole. He has high empathy for founder vision, but is at the same time a pragmatist about what it takes to get products to market.Ali Davar · Co-founder and CEO, Atlas ID · 2020
Miles was instrumental in supporting us through an important transitional period as we focused on the long-term sustainability of our organization. Due to his efforts the past year we have a stronger foundation.James Griffin · Owner, Vancouver Film School · 2015
He consistently builds bridges within organizations that struggle with sprawl and siloed thinking. All of this, in combination with his talent at managing board conversations and securing support at the senior leadership level, made it incredibly rewarding to work for him even in the most challenging of scenarios.Mya McDuffie · Director of Product Management, Mediafly · 2025
It is the question I am asked most in this kind of work. In most cases I can help solve the problem in a fractional role. After the read we decide the shape together: coaching the top of the team, a part-time seat, or full time, interim or permanent. If the people are good and the company is set up to succeed, I will consider a longer role, and I will look at it as objectively as I looked at everything else. After the read, not during it.
I cannot give you an honest read while I am auditioning for the job.
What keeps you up at night?
Chances are I have sat on the inside of something like it. Start there. We can spend the whole first conversation on it.