Jason Holloway is a hands-on CFO and Finance Executive with over 25 years of experience leading strategic finance and operations across software, healthcare, real estate, consumer, and emerging sectors like AI and robotics. He has raised more than $500M in capital, executed multiple exits, and scaled businesses in diverse industries.
Known for diving into the details, Jason personally builds advanced financial models, leads system implementations, and collaborates closely with founders and boards to align financial strategy with execution.
A seasoned executive, entrepreneur, and investor, he partners with startups to design and execute effective growth strategies. Jason previously served as CEO of a venture software development company that invests in startups in the US and abroad, VP of Capital Markets at Digital Realty Trust (DLR, IPO), and Investment Banker at Deutsche Bank. He is currently the Chairman of the Board for Hyperbeard Games (Mexico’s largest gaming company), and has previously served on the boards of Cruzin, Elixar, and St. Francis Yacht Club.
Most recently, Jason has focused on AI-driven financial transformation, cost recovery, business model redesign, M&A, and strategic finance leadership for high-growth technology companies, including an AI-first robotics startup that’s reinventing American manufacturing.
Away from work, Jason enjoys sailing (he’s raced across the Pacific Ocean twice), traveling (103 countries and counting), and most of all, being a dad.