CHIEF EXECUTIVE OFFICER · WILTSHIRE VENTURES
Kevin R. MacCauley
Founder, exited CEO, and operating investor with 18+ years scaling B2B technology businesses at the intersection of small business, sports, and super intelligence. I built Upper Hand from a closet office in Maryland into a category-leading SaaS platform, carried it through a pandemic to profitability, and sold it to H3 Partners in 2026.
14
YEARS LEADING UPPER HAND TO EXIT
$1B+
CUSTOMER REVENUE PROCESSED
1M+
CONSUMER END USERS
74
BOOKS LOGGED
01 Background How a Little League coach with a cash box ended up running a category-leading sports SaaS platform, and where the work goes next. READ → 02 Resume Eighteen years across founding, sales leadership, and operating roles. Full career history, education, and recognition. READ → 03 Bookshelf Seventy-four titles, heavy on biography, ancient history, and the operators worth studying. BROWSE → 04 Speaking Podcast appearances, mentorship with Techstars and Butler, and availability for panels and founder sessions. READ → 05 Research Published research notes and policy advocacy, from the Comanche Curve to the open letter sent to Indiana's congressional delegation. READ → 06 News Fourteen years of coverage: funding rounds, acquisitions on both sides of the table, awards, and the 2026 exit. BROWSE →