Exit Stories: From Taxes To Taprooms, Silvia Aguirre Puts Family First

These days, Triangle entrepreneur Silvia Aguirre has her head in the clouds—Clouds Brewing, that is, the multi-location brewery and restaurant she and partner Matthew MacNeil founded in 2015. But in 2002, long before the couple ventured up into the beery stratosphere—and before Aguirre became an Exit Stories guest—her idea for a better way to manage sales tax exemptions and reseller certificates led the couple to create CertSafe, one of the first Triangle fintech SaaS solutions to hit markets.

Under the name Tax Technology Services, LLC., the pair grew the company for over 10 years until it was acquired by Avalara in 2013. Today, Aguirre serves as Avalara’s VP for Certificate Management.

Here are three key takeaways from this week’s episode:

  1. Like many entrepreneurs, Aguirre and MacNeil thought hard about whether or not to seek funding in Tax Technology Services (TTS)’s early days. One deciding factor, Aguirre said, was that reflections on MacNeil’s experience in a large Bay Area company led them to realize that when done irresponsibly, funding can lead to a lot of waste, and that was not what they wanted. In terms of staffing, TTS hired new people with software design and engineering as needed. When they started to close massive deals while still having a small number of employees, that is when Aguirre realized it was time to either grow or go. “We really grew a lot,” Aguirre said. “We were getting these massive corporations, and we’re a small company of probably 20 to 25 people, which is not a bad place to be. But at that point, we actually said ‘Wow, how much more can we take this?’” (15:07)
  2. When it comes to acquisitions, size matters—but not in the way you might think. TTS was one of Avalara’s first big acquisitions, but Aguirre wasn’t alarmed by the acquiring company’s relatively small size. In fact, she said, this was an incredibly positive consideration during the acquisition process, as the more intimate environment created space for members of the TTS team to grow alongside Avalara. “I saw the future for the company,” Aguirre said. “I go, ‘This company might be small right now, but I can see where they’re gonna go. And we can leverage this, we can jump into that bandwagon and get there faster than if we try to do it ourselves.” (16:45)
  3. Prioritize the culture you want your company to have, and value that culture even through the acquisition process. When Avalara offered to acquire TTS, one of Aguirre and MacNeil’s main conditions for the sale was that the family-first culture they created within the company continued to be a priority by keeping their workers located in the Triangle. The agreement to keep CertSafe based locally was big in two ways: their team was doing remote work long before it was cool, and the decision led in part to Avalara creating its current 500+ employee presence in the Triangle.  “They have a huge place here in Durham,” Aguirre said. “Obviously we started in our offices in downtown Raleigh, and it was not that big. But when the vision came about, I pat myself on the back because otherwise we wouldn’t be here today.” (19:50)

Thank you again to Vaco for sponsoring this season of Exit Stories. You can listen to this week’s episode (and subscribe!) below: