Their Startup Raised $131M And Nearly Died. A Hard Pivot To AI Has Them On The Way Back.

Sales engineering startup Vivun had buzz and a $500M+ valuation. Then it hit a wall. CEO Matt Darrow's refocus around AI agent Ava has it growing again.

Vivun’s exec team including its five cofounders, plus CMO Jarod Greene, CFO Kevin Spinelli and CISO Jamie Brown. Credit: Vivun

The Upshot

In June 2024, startup CEO Matt Darrow stood up in front of his board of directors to show them a demo, and hopefully save his company.

Not so long before, Darrow’s startup, Vivun, had looked like the next classic startup success story.

Vivun sold software for sales engineers – specialists who help salespeople close accounts by explaining and showing off the tech on offer. From nothing in 2019, Vivun had marched steadily to $10 million in annual recurring revenue by 2022, raising a total of $131 million in funding at a valuation that exceeded $500 million.

“We were on a tear, running across the chasm,” Darrow says now. “Then, everything basically stopped, like we were frozen in time.”

Instead of tripling revenue in 2023, growth slowed to a trickle, then stopped. “The first time you miss a quarter, it’s like, ‘that was weird,’” Darrow says. By the second quarter, it was a red alert.

---

Help shape our Upstarts coverage in just two minutes!

To deliver the startup stories you want next year, we need to know more about you, our readers. Please take two minutes right now to fill out this short audience survey.

It’s anonymous and crucial for us to bring you the right content, aligned with the right partners. (If you’re interested in sponsoring, you can check out our interest form.) As a year-one startup, we really appreciate your feedback.

---

Darrow and his four cofounders (they include two married couples) didn’t want to cut their losses by trying to sell the business, or returning money to investors by shutting down.

Instead, they went all-in on the tech they thought would otherwise disrupt their business, anyway: AI. At the board meeting, they presented Ava, an AI sales agent that can serve as an automated sales engineer for leaner teams.

Thanks to Ava, Vivun now finds itself mid-turnaround. The startup projects Ava to generate $10 million in ARR by year’s end, tripling next year. Achieve that, and it will eclipsed Vivun’s original software business, built up over four years, in just 18 months.

It hasn’t been easy – Vivun laid off more than half its staff as part of its pivot – and it’s far from over, as questions remain about how customers will resonate with bringing AI avatars – Ava can appear in video format like a digital teammate – into live calls.

Vivun’s is not even the only Ava, as controversial billboards in San Francisco telling you to “stop hiring humans” have pushed another startup’s Ava sales agent. (There are others, too.)

But Darrow and his cofounders push has at least given their startup new life in the face of entrepreneurial doom. And the tools they’ve built, while still very early to acceptance, are already helping businesses sell more with their own leaner teams.

“I’m still here talking at this table,” Darrow says. “So we’re lucky.”