I once worked with a founder who had $15M in revenue but was driving straight at a cliff. He had...
Osprey Strategies works with founder-led businesses doing $5M–$100M in revenue — helping leadership teams build the sales functions, operational infrastructure, and strategic clarity that turn founder-dependent growth into scalable growth.
What worked at $5M doesn't work at $20M. Decisions that used to be obvious now require data you don't have. Your leadership team is strong but flying on instinct. You need structure, but you don't want to lose the culture that got you here.
Revenue keeps climbing — but it climbs because of your relationships, your instincts, your hours. The team is good, but the machine doesn't run without you in the room. At some point, you're the limiting factor.
Your financials look good. But customer concentration, key-person dependencies, processes that live in someone's head — these are the things that cost real money in any serious conversation with an investor or partner. Most founders don't find out until it's too late to fix.


Every founder-led business hits a point where the founder's instincts can't keep up with the business's complexity. We work with leadership teams to build the strategic clarity, management systems, and decision-making frameworks that let you scale deliberately, without losing what made you good in the first place.
When a transaction makes sense — whether that's in two years or five — the founders who get the best outcomes are the ones who started preparing long before they were "ready." We bring a buyer's perspective to every engagement, because we've spent years on the other side of the table evaluating hundreds of businesses.


When a founder-led business is ready to scale its sales and marketing, the challenge isn't effort — it's building a process that works without the founder driving every deal. We help you turn what's working into something repeatable.


I founded Osprey Strategies to be a flexible advisory and investment platform. My background spans sales, operations, and finance - including roles at Wayfair, Axon, Bridgewater Associates, as well as founding and running my own investment fund. I've evaluated hundreds of founder-led businesses from the buy-side - and the learnings shape my efforts at Osprey. I work with founders, management teams, and investors to drive growth, pursue acquisitions, and professionalize businesses. Whether through consulting, advisory, or co-investment, my goal is to help businesses see further, move faster, and scale smarter.
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