Welcome to Episode 159! Fred Shilmover is the CEO and co-founder of InsightSquared, one of Boston’s premiere tech startups paving the way in the sales intelligence space. Throughout the InsightSquared journey, Fred has raised over $25m in VC funding from the likes of DFJ, Bessemer, Salesforce, and Atlas Venture. Prior to founding InsightSquared, Fred was a corporate development associate with Salesforce Ventures, and before that he held several key roles at Bessemer Venture Partners, including associate and Director of IT. He is also a board member of TUGG, an organization that brings together tech entrepreneurs with social enterprises that support at-risk youth.  

In Today’s Episode You Will Learn:

* How Fred made his way into the world of SaaS, hustled his way to being a VC with Bessemer, and then came to found InsightSquared from Boston.

* Why does Fred strongly argue that it is easier to start with SMB and move to enterprise than enterprise down? What are both the technical and personnel considerations of the decision? Why is it the product manager’s job to lose complexity as slowly as possible?

* Why does Fred disagree and state that CAC/LTV is not the guiding metric for SaaS startups? What are the core problems of CAC/LTV? What alternatives should founders consider as their guiding metrics? Where does Fred believe most founders go wrong when assessing their metrics? What metric keeps Fred up at night?

* What does Fred believe are the fundamentals to successfully building an inside sales team from scratch? What is the lowest ACV that an inside sales team can justify? How does Fred look to create a culture of accountability and responsibility without the element of fear of not hitting quota?

* Why does Fred go against conventional wisdom and suggest that customer success is the responsibility of the entire organization? Why is this advantageous compared to a dedicated CS team? How does this mean both time and teams are allocated towards customer success?

60 Second SaaStr

* What does Fred know now that he wishes he had known at the beginning?

* What is the least discussed but most worthy topic in SaaS?

* What would Fred’s biggest advice to emerging SaaS founders be?

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Jason Lemkin
Harry Stebbings
Fred Shilmover

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