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

Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization's go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise.

In Today's Episode We Discuss:

• How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today's leading COOs with HelloSign? What were Whitney's biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality?
• What does truly successful exec leadership look like in Whitney's mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a "big company" person?
• What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and centre in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider?
• COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO?

Whitney's 60 Second SaaStr:

1. What does Whitney know now that she wishes she had known at the beginning?
2. What makes for the optimal relationship between COO and CEO?
3. What is the most challenging element of Whitney's role with HelloSign today?

Read the full transcript on our blog.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin

Harry Stebbings

SaaStr

Whitney Bouck

Ever feel like you can't really connect with prospects or have an organized workflow to get deals closed? Outreach.io, the leading Sales Engagement platform, supports sales reps and their managers by making it simple to humanize and personalize communication at scale; automating the soul-sucking manual work; and dramatically increasing the productivity and efficiency of all revenue-generating teams. You can check them out at outreach.io/saastr to chat with them and receive a free copy of their new book -- Sales Engagement: How The World's Fastest-Growing Companies are Modernizing Sales Through Humanization at Scale.