Drake Pruitt is Chief Executive Officer of SundaySky. He is a seasoned executive with more than 30 years of experience in enterprise software. Drake also serves as an Operating Partner with Clearhaven Partners, the controlling
Drake Pruitt
Archives: Team Members
Bill Henry
Bill Henry serves as Chief Commercial Officer at SundaySky, where he oversees all facets of the SundaySky Advertise business, including sales, go-to-market strategy, partnerships, and revenue growth. In this role, Bill is responsible for building a scalable, high-performance commercial
Alice Milligan
Alice Milligan is an accomplished C-suite executive with more than 35 years of experience leading transformational marketing, customer experience, and digital innovation across global financial services, banking, payments, retail and telecom industries. She is recognized
Mark Flaharty
Mark is a recognized technology and software leader, bringing more than 25 years of experience in building and growing mission-critical technology companies and helping to bring them to maturity. His most recent work has been
Brendan Cournoyer
Brendan Cournoyer is Vice President of Marketing at SundaySky, where he leads all strategies specific to demand and pipeline generation, product marketing, operations, brand, and content. Over a career spanning 20+ years, Brendan has led
Tammy Martin
Tammy Martin serves as the Chief Financial Officer of SundaySky, the world’s leader in AI-powered, personalized enterprise video platforms. With over 25 years of experience across founder-led, venture capital, and private equity-backed software firms, she
