One partner spent decades investing in great businesses. The other built and sold them. This is who leads HarborWind — and what it means to work here.
Before HarborWind, Rocky spent 14 years in investment and financial leadership roles, most recently as Principal and CFO at a Chicago-based family office. In that seat, he led the full lifecycle of lower-middle-market acquisitions — originating deals, structuring capital, managing due diligence, and overseeing portfolio company performance. He’s the person in the room who can look at a set of financials and see both the story they’re telling and the one they’re hiding. That discipline — rigorous, skeptical, but never cynical — is what we bring to every lower-middle-market industrial we evaluate.
Sean is a founder who became an investor — and that sequence matters. He built AndPlus, a technology consulting firm, from the ground up. He negotiated its sale to Ensono, a platform company backed by KKR. Then he stayed and ran Ensono’s North American consulting division, learning firsthand what it looks like when private equity does its job well. He founded HarborWind to bring that same operator-first approach to the lower middle market. He brings something to HarborWind that most investors can’t: the memory of what it feels like to hand over a business you built. That empathy isn’t soft. It’s a strategic advantage in a market where founders choose their buyer.
Two partners. No layers. That structure is the point —
and it shapes every role on this team.
Screen inbound deal flow. Research industries. Build the initial investment thesis before anyone else sees the opportunity. You are not reviewing someone else’s work — you are creating the first draft of the argument.
Build the LBO models and operating cases. Join diligence calls with management teams. Your analysis is the analysis — there is no separate team that “checks” your work and presents their own version.
Support transactions through close. Work with portfolio company teams on performance improvement, integration planning, and strategic initiatives. See the full lifecycle of a deal, not just the pitch.
Careers at HarborWind
Most early-career roles in finance are designed to keep you at arm’s length from anything that matters. You will learn the mechanics. You will not touch the machine.
We don’t operate that way.
At HarborWind, every person in the room is there because they are needed — not because the org chart says so. Our team is small by design. That means every analyst, every intern, every new hire is a core contributor to live deals, real diligence, and actual investment decisions.
We are not for everyone. We are for the people who would rather be stretched and learning than comfortable and waiting.
First dedicated analyst hire. Full deal lifecycle exposure from day one — sourcing, modeling, diligence, execution, and portfolio company support. Your work product goes directly to the decision-makers. No intermediary layer.
Apply NowReal deal immersion, not a simulation. You’ll build models on active targets, run diligence workstreams, and contribute to sourcing strategy. Culminates in a sector thesis presentation that could shape our acquisition pipeline.
Apply NowSend your resume and a short note on what draws you to HarborWind specifically. Not private equity generally. Us.