Jenn Longnion

Jenn Longnion is a Chicago-based operator-angel affiliated with See and Free Consulting, writing sub-$25K checks at pre-seed and seed into health IT software and digital health. The check size is small by angel standards, which positions her as an advisor-and-signal investor rather than a meaningful capital source, and the consulting affiliation suggests a healthcare-operations and provider-services background that translates to operating advisory rather than capital-led value. AI is not flagged, so the framing is on practical health IT, provider workflow, and digital health software rather than algorithm-led pitches. The Chicago base provides access to Midwest healthcare provider systems, the broader Chicago digital health investor and operator community, and the regional payer ecosystem. Founders most likely to fit are early health IT and digital health teams selling into Midwest provider systems and payers, clinical workflow software with a clear operations-focused buyer, and any team that benefits from a healthcare-operations consultant on the cap table for early pilot design and customer references. Biotech, devices, life sciences tools, and consumer wellness are weaker matches. The check itself will not move a round, so founders should treat the engagement as advisory-first, with the small check serving as a signal of conviction. The entry path is a LinkedIn message, preferably warmed by a mutual Midwest healthcare or operator connection, leading with the operations problem, the buyer persona, and the specific consulting and pilot-design help her profile materially provides at pre-seed and seed stage.