The first startup Andrew Wynn joined became a multi-billion-dollar home run.

The first he started sold to Hippo Insurance in 2019.

Now, the 35-year-old leader is swinging for another smash hit — this time in the world of insurance financial operations. Wynn is the CEO of Ascend, a software platform that automates billing, collections and accounting tasks.

With a notable growth step planned for early 2025, he’s hopeful that Ascend will become the “financial system of record that helps collect premiums, disperse premiums, disperse claims, remit commissions — all of those things.”

From West Africa to Silicon Valley

After graduating from Purdue University in 2011, Wynn joined the Peace Corps, where he worked in economic development consulting in Senegal for a couple of years. When he returned to the states, his fascination with technology, computers and software led him sight unseen to San Francisco.

Wynn got a job in Levi Strauss & Co.’s technology leadership program. Near the end of that experience, his roommate was working at a small startup, and before Wynn moved out, he was invited to work with him. That little company became Instacart — an online grocery delivery company that ballooned to a valuation of $39 billion in 2021.

“It was very stereotypical; it was like the TV show ‘Silicon Valley,'” Wynn remembered. “A bunch of guys hanging out in a house, drinking beer at night. Literally in a house. Like, I’m not exaggerating. Someone’s desk was in a shower because we ran out of space.”

Watching the business grow from those roots to the tens of millions of orders it completes today showed Wynn the ropes of a startup. Instacart’s success gave him a front-row seat to the inner-workings of a successful company.

Wynn shared that it’s “very rare” for a company to be that successful, though, “and so you’re a little spoiled, and you’re like, shouldn’t all startups go to the moon instantly and be a rocket ship? We’re kind of always chasing that again and working to build the biggest, most successful company we can because of that.”

Entering Insurance

Not long after leaving Instacart, Wynn launched Sheltr alongside his former colleague Praveen Chekuri, who also worked at Instacart in the late 2010s. Instead of creating an online grocery marketplace, the pair’s new business was “a home maintenance platform that helped homeowners proactively care for their homes to catch and mitigate issues before they become costly repairs,” per a press release.

It marked the duo’s first steps into the insurance industry.

They knew they didn’t want to acquire individual customers one at a time. So, leaning on what they learned while working at Instacart, Wynn and Chekuri prioritized partnerships with brands that customers already trusted.

How could they do that with home services? By teaming up with insurance companies.

Their timing was right. Sheltr launched in the late 2010s, back when the full stack carrier model was gaining popularity with InsurTechs like Lemonade, Root, Metromile and others that hadn’t yet grown into full-fledged companies.

“We got super lucky, though, because we started selling into those folks,” Wynn explained. “And everyone was watching what they were doing. And so, as a result, there was a little bit of FOMO from the bigger carriers … so it accelerated our business very quickly, being able to sell into [bigger carriers].

Sheltr sold to Hippo Insurance in 2019. It lives today as Hippo Home Care.

Ascend’s Origin

Wynn and Chekuri pulled back the curtain of the insurance world during a year at Hippo, observing how the MGA worked with appointed independent agents, its captive agency and joint venture agents. They took note of underserved opportunities for improvement as they fell in love with the industry.

“We didn’t know anything about underwriting,” Wynn said, “and turns out, all of these people who have been underwriting for hundreds of years as companies are really good at it. I think that was a little bit of a miss with that full stack carrier approach.”

Traditional carriers have the edge in underwriting and distribution — what Wynn described as “core competencies of insurance businesses.” But carriers are “not good at lots of other stuff,” he said. So, he and Chekuri set out to start a company that enabled insurance businesses to focus on those core competencies.

That company became Ascend. The software platform was launched in mid-2022 and has morphed into an all-in-one solution to unify insurance invoicing, payments, and accounting tasks. The business has tripled its revenue each year as more insurance businesses focus on efficiency through technology.

“And that has served us incredibly well, because that is what we do,” Wynn said.

Ascend works with a few thousand retail brokerages, as well as MGAs and wholesalers, and next year, the company will begin working with insurance carriers. Ascend’s mission is to address friction points in the insurance value chain and drive interconnectivity between all parties involved.

“It’s ultimately a loop,” Wynn said of the value chain, “and what we see happen is, at all of these interaction points, there’s not software that communicates across that. That’s why agency management systems are different from policy management systems. And so that’s where manual work is created; that’s where inefficiency’s created; that’s where data entry issues are created.”

Evolving as a Leader

As Ascend grows and reaches a wider audience, Wynn is realizing that what made him successful in building the company to where it is today is not the same as what will make Ascend successful moving forward.

“And that’s a real evolution,” he shared, “and something I personally need to sort of evolve [into]. And probably every founder, CEO, [or] leader who’s in a rapidly growing company needs to.”