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Phillip Cunningham
Vice President, Strategic Development & Investor Relations

Software founders and management teams have an incredible opportunity to breath an idea into life, nurture the “there’s a better way” notion into fruition and propagate their vision to the world. The challenge is compelling and the future is bright. Partnering as consiglieres with these renegades and builders who share our affinity for focus, endurance and thoughtful conviction represents an amazing mission, one that motivates us each and every day.


Phillip has partnered with software entrepreneurs and management teams as an operator, investor and advisor throughout his career. He leads PeakSpan’s Strategic Development Program to assist portfolio companies in exit preparedness and Investor Relations efforts where he manages stakeholder communications.  Prior to his current role, he served at Cloudbeds (a PeakSpan portfolio company) as Head of Corporate Development where he led the Company’s $150M Series-D financing and three acquisitions. Previously he worked as an investment team member (PeakSpan Fund I and Fund II) after advising late-stage software companies at Goldman TMT San Francisco and serving as an Air Force Officer. Phillip holds a B.S. in Operations Research from the United States Air Force Academy and an M.B.A from New York University. An Austinite (and landlocked surfer), Phillip can be found at the Waco Surf Park or spending time with his wife, and two daughters enjoying the beautiful Hill Country outdoors.