You want a second set of eyes on the roadmap.
I read a roadmap the way an investor or an acquirer will: what it costs, what it bets on, and whether the architecture underneath can carry it.
You are weighing technical alternatives.
Build, buy or integrate. I write the requirements and success metrics before choosing, so every option has a number to beat.
You are moving off a platform that no longer scales.
Consolidating stacks after an acquisition, migrating off home-grown software, replacing a vendor. I decide what to sunset and which architecture wins, then move the business without stalling it.
You just closed an acquisition.
Integration is where deals lose their value. I integrate the systems and the business operations, and I would rather start the plan before close than after.
You need a product or technical solution architected.
I architect the solution myself, not only the requirements, and I stay with it through certification and security review.
You are building out the team.
Structure, operating model, standards, and the training that makes them stick.
You are scaling operations.
Growth should not mean hiring in proportion. I look for the step that makes every new customer or transaction cheaper than the last.
Your AI pilot never left the lab.
I move AI into the work itself, with people handling the exceptions and judgment calls, and measure it against the process it replaced.