SaaStr 260: HelloSign COO, Whitney Bouck on How Startups Can Attract The Most Seasoned Execs In SaaS, How To Determine Whether A Seasoned Exec Has True Startup Fabric & What Separates Good From Great When It Comes To COOs

In this episode of The Official SaaStr Podcast, Harry Stebbings interviews Whitney Bouck, COO at HelloSign (now part of Dropbox), about executive leadership, scaling SaaS companies, and the evolving role of the CIO. Whitney shares her experiences from Box and HelloSign, offering insights on managing hyper-growth, preventing employee burnout, and setting ambitious yet achievable goals. She discusses the importance of aligning teams with a company's North Star, the right timing for building out an executive team, and how to attract seasoned executives to startups. The conversation also covers the transformation of the CIO role into a strategic driver of innovation and customer experience, as well as the key attributes that differentiate good COOs from great ones, emphasizing the need for efficient processes and strong partnerships within the business. Whitney also shares her perspectives on hiring practices, onboarding new executives, and the balance between pace and quality in hiring, and concludes with personal insights on focus, optimism, and the importance of taking breaks.