Bill Simpson is a multi-time CTO who advises Mainsail portfolio companies on scaling and infrastructure buildout, technology best practices, and effective AI strategies. He also serves as a mentor to CTOs and advisor to CEOs on building technology to maximize value for customers.
Bill is an experienced technology executive having spent nearly three decades leading product and engineering teams, scaling B2B software companies, and helping drive significant value creation.
Bill is currently the CPTO at Red Oak, a Mainsail portfolio company. Previously, Bill served as CPTO of Ncontracts, an integrated risk management solutions for financial institutions, and a former Mainsail portfolio company. During his tenure, he was instrumental in helping scale the company, including helping expand its client base, integrating half a dozen acquisitions, and successfully navigating two private equity exits.
Prior to Ncontracts, Bill held senior technology leadership roles at Ingo Money, where he helped develop an innovative real-time payments network and mobile check guarantee for the underbanked space, and ProfitStars (a Jack Henry Company), overseeing remote deposit capture and ACH products. He also led core software development at MDR (a D&B Company) and platform development at Cerebra, a semantic web and AI technology startup. Bill takes a team-first approach to technology problems and believes in the power of team-based execution and scale-up. Bill’s prior board experience includes RegEd and advisory work to Meazure Learning.
Bill holds a BSc in Computer Science from Boston University. He resides with his wife, son and dog in Franklin, TN.
Outside of Mainsail
Bill enjoys the outdoors, spending time with his family, reading, and fitness activities of any kind.
