Greg Strickland
COO at Productboard at the time of recording, focused on scaling from SMB to enterprise across product, sales, and cross-functional operations.
Between Two COOs episodes featuring Greg Strickland
About Greg Strickland
Greg Strickland served as COO at Productboard at the time of his Between Two COOs appearance, where he focused on the company's expansion from an SMB customer base into enterprise. With more than 20 years of experience spanning individual contributor and executive roles, he has built a career on saying yes to cross-functional projects and zero-to-one builds.
His operating philosophy prioritizes business outcomes over personal career path. He has stood up new departments, hired across disciplines, and stretched into functions outside his comfort zone because the company needed someone to figure it out. That pattern of taking the hard, ambiguous assignment is how he describes the path to COO.
On the show, Greg discussed when to say yes and when to recommend someone else for the job, how to push back on CEO strategy when you disagree, and the operational shifts required to move a SaaS company upmarket.
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