Clients have been anonymized.
The venture-backed software company getting ready for whatever comes next
About 30 people, fully remote, roughly $30 million raised, revenue approaching $10 million, selling enterprise software into a regulated corner of healthcare with a concentrated customer base. Over three years we raised capital three times, two equity rounds and one debt facility, and ran a five-firm RFP to bring in a Big Four auditor and get the company audit-ready. The more important work was operational. We planned the turn in sales velocity, pushed cost discipline into engineering and operations, and built margins that beat the market, so the valuation grew with every round.
The $200 million sale, from the inside
At a $50 million healthcare software company owned by an asset manager, I was chief of staff to the CEO and twice interim head of finance over four years. The job was the budget process, the board, two clean audits, the company's operating cadence, and resetting the finance team, and then quarterbacking a $200 million sale that returned top quartile for the sponsor.
The software company that was out of money
A single-digit-millions revenue business with a product its customers needed and a cash position measured in weeks. The board brought me in. Taxes had not been filed for five years and the books had never been kept correctly, so I fixed both and put one weekly number in front of everyone. Then I worked with the team to drive the board to a refinancing and a path to exit. When the round closed I handed the books to an outsourced provider and left.
The family office that needed to run like a portfolio
A principal with a large, mostly illiquid balance sheet, debt with several lenders, operating businesses and properties in several states, and a spending pace that had produced a liquidity crunch once before. The finance function reported on what had happened. Nobody was running the whole as a portfolio. I flew out to meet the people who run each business and property, carried the principal's strategy to them and their constraints back to him, and got the group aligned on where capital would and would not go over the next two years. The principal and his team now see debt, capacity, and headroom on one page every week, and the governance we agreed treats hard limits as tripwires for a conversation rather than rules nobody follows.
The live entertainment company deciding where the next dollar goes
Productions in several cities, and a choice with every dollar between a new city, a new show, and more of what already worked. The owners had never seen results by production, so the first job was giving them that view. The second was harder. We spent several months in a direct negotiation about whether the company was solvent on its current path and what it should become over the next five years. The answer changed where the next dollar went, and the one after that.
The healthcare operator that outran its own books
A founder team bought a struggling regulated business with no historical financials in the data room, then added locations and sister companies until there were eight legal entities and one part-time controller shared with other businesses. By the time I arrived revenue was running several times the prior year, there was no accounts payable file, and the team could not get through a board meeting. We hired a full-time controller, moved the banking, and built a consolidation that let the owners see the group as one business for the first time. More important, the owners stopped making decisions from bank balances. When the largest customer renegotiated, management could go to the board with a solid plan and keep the confidence that turned into growth the following month.
