MacInnis: Startups Must Solve Problems Sequentially, Not via Massive Roadmaps
Matt MacInnis · What Mistake Founders Make With A-Players | Matt MacInnis | COO Rippling · Feb 7, 2026 · at 23:49
Matt MacInnis, COO and CPO of Rippling, discusses operational velocity and the limits of long-term roadmaps in fast-growing startups.
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“You want the archetype of the person whose instinct is to just do surgery after surgery after surgery all day, all night to, and not sort of zoom out and build some massive roadmap of things to do, but just to like to take the next proximal problem, beat it down until it's no longer, not perfect, but beat it down until it's no longer the most important problem in business, and then turn your attention to what has emerged next. As the most important problem in the business, which by the way is almost never knowable in advance. You don't know when you beat down problem a what problem will emerge as the next most important problem. And so the only thing you can do is work in series as rapidly as you can sort of as problems emerge.”
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