He Didn't Want to Lead His $1 Billion Business the Same Way Anymore — Here's How the High-Stakes Switch-Up Paid Off Advait Shinde, co-founder and former CEO of educational software company GoGuardian, was ready for a change. So was former COO of LegalZoom Rich Preece.

Advait Shinde, co-founder and former CEO of educational software company GoGuardian, spent a decade building a business that optimizes digital learning experiences at scale — all the way to a $1 billion valuation.

It began in 2014 when Shinde and his co-founders Aza Steel, R. Todd Mackey and Tyler Shaddix "accidentally timed the market perfectly," Shinde tells Entrepreneur. Although investors gave them "pretty disheartening" feedback about the market size and associated challenges, the trio bet big on the influx of devices in the classroom, including Chromebooks, and were successful.

GoGuardian closed a Series A round in 2015 but didn't spend the money because school districts paid for multi-year contracts upfront, making for a "very cash-generative" model.

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Shinde became the CEO of GoGuardian in November 2017 and led the company through an impressive period of growth. With Shinde at the helm, GoGuardian acquired edtech companies Pear Deck, Edulastic and TutorMe; launched its gamified learning product Pear Practice; and secured investments that earned the company its unicorn status.

"The challenge of running the company at this scale was very different from the challenge of running it when it was 10 times smaller."

However, earlier this year, Shinde decided he didn't want to be GoGuardian's CEO anymore.

"The challenge of running the company at this scale was very different from the challenge of running it when it was 10 times smaller, even 100 times smaller," Shinde says.
"After a lot of introspection, I realized that the things that I am most excited about and perhaps the best at had much more to do with early-stage product development and working with smaller teams."

According to Shinde, GoGuardian needed a leader who could help the company continue to thrive at its current scale and beyond. So, following several conversations with the board, the company decided who the ideal candidate would be: someone who could fit within GoGuardian's unique culture and had a penchant for problem-solving. That criteria led them to Rich Preece, former COO of legal services company LegalZoom.

^{Image Credit: Courtesy of GoGuardian. Rich Preece.}

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"Do I uniquely have experience where I can add value?"

Before joining LegalZoom, Preece spent 17 years at Intuit and witnessed scale in TurboTax and QuickBooks, but he had no experience in edtech and admits stepping in as GoGuardian's CEO "wouldn't have been the most natural fit." Still, Preece kept an open mind and considered several points that ultimately solidified his decision to take the role.

"One is, Am I passionate about the space and the mission?" Preece explains. "The second thing I look at is the quality of the products. And then the third element I look at is, Do I uniquely have experience where I can add value?"

According to Preece, Shinde's enthusiasm was contagious from their very first conversation.

What's more, as the father of a 12-year-old, Preece had firsthand experience with "one of the fundamental problems in education in the U.S. and around the world" — that teachers with dozens of students "by necessity, set the standard for the middle third."

"If you're in the top third, you don't necessarily accelerate as much as you could have," he says. "GoGuardian's products [unlock] customization and personalization for educators [and] allow the educator to pull the bottom third up, meet the middle third where they are, and the top third to accelerate beyond where they otherwise would have done."

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Finally, Preece thought that his expertise could benefit GoGuardian going forward.

"I have had the good fortune of building knowledge about how companies scale and how you provide operational rigor around those good products and how that operational rigor benefits both employees and customers as we scale," Preece says.

"[We] work very closely together in terms of forward-looking strategy and overall company architecture."

Preece transitioned into the CEO role in April, and Shinde became executive chairman of the board. It's Preece's first time serving as CEO of any company, and he says people warned him it could be an interesting and challenging dynamic when a founder is still involved. However, Preece and Shinde took steps to ensure working together wouldn't be an issue.

From the start, Shinde and Preece had open conversations about their roles to ensure alignment. "He and I work very closely together in terms of forward-looking strategy and overall company architecture," Preece says. "But then, day-to-day, Advait is still very much involved with the engineering community, where he is an innovator and a leader."

Despite the rise in remote-working relationships, the duo was also intentional about meeting in person numerous times. At one dinner, they even brainstormed a situation where they disagreed to determine how well they could navigate differences. "These are relationships you're hoping to build for a significant period of time into the future," Preece explains, "so doing that work upfront and spending the extra time and care and attention has certainly paid off."

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"Anticipate where there might be differences in approach, value system or principles."

Shinde agrees — and advises any leaders going through a similar transition to do the same.

"Be fully aware of how high the stakes are and how emotional intelligence is going to be critical to navigating the road ahead," Shinde says. "And then anticipate where there might be differences in approach, value system or principles, and get ahead of that to identify where you align and misalign. We did a lot of that work upfront."