Exit Stories: Matt Williamson, Windsor Circle

In this week’s Exit Stories, host Kevin Mosley talks with Windsor Circle Co-Founder and former CEO Matt Williamson, on how he saw a market gap while working as an executive at Bronto and managed to turn that into a successful predictive-marketing startup.

Windsor Circle, with its strong culture enabling it to grow cohesively through multiple funding rounds, eventually strategically exited to the private equity-backed email marketing company WhatCounts in 2018. 

And of course, thanks to the sponsor of Exit Stories, Dualboot Partners!

Some of the episode’s highlights:

  • All four co-founders of Windsor Circle committed to go a year without income at the beginning. Even when investors started coming in, “every bit of funding went to accelerate sales, not towards income,” which helped them hit key milestones, Williamson said. [16:00]
  • Windsor Circle was a part of the package of high-growth digital companies that WhatCounts—an email marketing company—was acquiring at the time.  “It was a strategic acquisition, but had the flavors of a private equity play, because a couple steps above it was driven by private equity,” Williamson said. [38:50]
  • If 2014 was the heyday for Windsor Circle, then 2016 was when they started realizing they had an ease-of-use problem in the mass market that they didn’t have with the early adopters, Williamson said. In order to allocate sufficient resources to deal with the customer churn problem, over half of their employees had to be let go. [29:10]
  • The good news is, other companies jumped at the chance to hire Windsor Circle employees when they heard they were available—even if they weren’t initially planning on hiring. Williamson said all of the employees that were let go were given offers within a week and a half, and one employee even received 19 offers. “It was a very good representation of what we had built and the kinds of people we attracted,” Williamson said. “It was a truly unique team of people that were wildly committed to the vision.” [43:30]

To hear more from Williamson, listen (and subscribe!) to the full podcast below:

Or, if you would rather watch a video of the episode, click here:

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