Vice President / de facto CFO

Context

A friend's dad recruited Tim as de facto CFO, knowing he was a math whiz coming off Brown Advisory. CyberSpa built proprietary technology that would rebuild Windows PCs from scratch — reinstalling clean copies of the operating system, Office, and all apps — completely removing viruses and accumulated cruft. The business model was licensing this tech to large national retail brands.

Tim was responsible for landing the company's primary strategic client — Staples (at the time the #2 e-commerce business in the US and a Fortune 500 brand) — using a mutual connection to the Staples CEO to open the door.

Numbers

• Grew the Staples EasyTech pilot from 2 stores in MD → 10 stores in FL → 200 stores in CA.SalesStrategy
• Secured commercial financing to build 200 CyberSpa machines and deploy them into Staples stores — unlocking growth with limited cash on hand.FinanceFundraisingStrategy
• Handshake deal in place for expansion to 1,400+ Staples stores — would have been "millionaires overnight."SalesStrategy

What broke

• Staples shut down its EasyTech operation in March 2013.
• The Staples CTO who had been Tim's champion was put on probation (later fired).
• CS&P scaled back significantly. Tim, as de facto lead financial officer, effectively laid himself off.

Signature lesson

"Never put too many eggs in one basket, even if it's a promising basket." Tim still cites this. It shows up later in how he built Heady (broad client base, low churn).

Interview-safe stories

• "2 stores to 200 to 1,400 — and then zero." The full arc, including the handshake deal and its collapse. Great cover-letter opener for "resilience" and "concentration risk" prompts.SalesStrategyFinance
• "You were 24 and running the CFO seat — how?" — Family-friend network + Brown Advisory rigor.FinanceManagement

Skills exercised

Enterprise pilot expansion, executive-champion cultivation, financial modeling, scenario analysis, securing commercial financing, direct CEO reporting line, orderly wind-down of a business.