A boutique consultancy for legaltech and healthtech — built around partners who have spent careers inside the institutions our clients are trying to win. No junior staffing. No handoffs. Every engagement runs through the principal, start to finish.
The firm's principal is a builder by reflex — co-founder and CTO of CHESS Health, initial VP of Engineering at Talkiatry during a period of significant growth, and currently acting CEO of Case Compass and fractional CRIO at DB Legal Support / McCune Law Group and affiliate firms. Stilwell is where the threads come together.
The instinct started early. He was writing C and C++ before most peers had touched a compiler, working through advanced data structures at an age when most future technologists were still learning what a loop was. That foundation shows up today in the way he reads architectures and evaluates technical risk — not from a slide deck, but from first principles. The firm's engagements benefit from a principal who can sit in a code review without translation.
He also brings clinical-trial experience most technologists don't have — having served as principal investigator on studies at the Ottawa Hospital Research Institute (OHRI) in Ontario. That background shapes how the firm's healthtech engagements are run: with operational discipline, regulatory awareness, and a clear sense of what evidence actually requires.
The firm is named for John Joseph “Jack” Stilwell — an agricultural chemist by trade, a farmer in all seasons, and the head of a long family by every measure that mattered.
He worked in industries where a small mistake compounded into a real one, and where being trusted in the room was earned slowly and lost quickly. He kept the same standard at the kitchen table that he kept on the plant floor. The firm tries to keep his standard.
Jack and Joey share a birth month — both Tauruses. The bull on the firm's mark is for both of them, which feels right: stubborn bloodlines tend to run.