Employees who leave this Boston company get an unusual going-away present: five-figure checks to launch their startups

“If you’re hiring the best people in the world,” Hallen said, “some are going to leave and start companies. And a goal we have for Boston is to have much greater entrepreneurial density.”

David Henriquez started working at Klaviyo in 2018, when the company had about 100 employees. During his first month, he was drinking beer with Bialecki when the cofounder asked Henriquez about his plan for the next five years.

“I said, ‘I’m going to work here for five years, and then I’m going to start my own company,’” Henriquez recalled. “And [Bialecki] said, ‘That’s what we hope for.’”

Henriquez stayed for slightly more than five years before leaving Klaviyo last fall to cofound Hawk with Sean Marshall, who was Klaviyo’s senior vice president of sales. Hawk uses artificial intelligence to help companies create more marketing and advertising content — and then analyze what is most effective at persuading people to buy.

Hawk is still in stealth mode but planning to announce the product and funding in January. But Henriquez said that Bialecki “was the first email we sent when we were starting the company, and the first check we got.”

Andrew Smith developed a project in his free time while he was an employee at Klaviyo. His concept was to help companies get more people into marketing databases by creating games and sweepstakes that people could enter by scanning a QR code.

He turned to Bialecki and Hallen for advice on how to enhance his idea. Later, when he decided “to try giving it a whack,” he told Bialecki, “If I get your backing, I promise you I’ll figure it out.” Bialecki invested $50,000 and Hallen $25,000.

Smith’s company, Swapt, now works with customers such as food delivery company DoorDash and sportswear manufacturer Puma, and has raised nearly $1 million.

Michael Kurson and Jared Mintzlaff worked in sales and business development at Klaviyo, and one of the things they agonized over was writing personalized emails to book meetings with prospective customers. “It was the worst part of my job,” Mintzlaff says.

They formed a startup, First Touch, to address that.

Their solution uses artificial intelligence to personalize the email by first gathering information about the person and company to whom you’re writing. Their software might notice that the company is hiring for specific roles; that it has made a recent acquisition; or that the person has been a guest on a podcast. It allows you to create a formatted email and then fills in the specifics using AI; you review it before it gets sent.

First Touch already has several hundred sales reps at companies such as Klaviyo, HubSpot, and Zoom, using an early version of the software. It recently raised $3 million from investors — including Bialecki and Hallen, as well as HubSpot cofounder Dharmesh Shah. (Mintzlaff also previously worked at HubSpot as an account exec.)

One of the earliest companies to spin out from Klaviyo, Wonderment, helps online merchants deliver information about what happens after they receive an order. The software updates customers on the status of the order and lets them know if anything goes wrong along the way.

Wonderment cofounder Brian Whalley says he initially proposed the concept while still at Klaviyo, but didn’t get traction at the company.

So Whalley left Klaviyo in late 2019 to start Wonderment. After filling Bialecki and Hallen in on his progress in an email, Whalley said, they both wrote a $25,000 check. The company has raised $6 million so far, and has 15 employees, about half in Boston.

Whalley said he still talks about new features for Wonderment with former colleagues at Klaviyo: “They have been an amazing partner, even though I quit to start something else.” (He admits, though, that Klaviyo did at one point ask him — nicely — to stop recruiting its employees.)

Several of the companies founded by Klaviyo alumni, like Swapt and Wonderment, can be connected to Klaviyo’s software, so in effect they’re creating new features and capabilities for their old employer — making its product more compelling.

But being a Klaviyo alumnus is no guarantee of funding. Chathri Ali worked for Klaviyo for two years as a remote employee in Austin, Texas, before starting a company to help hospitals hire doctors more efficiently. At a meeting with Ali earlier this year, Hallen said he felt it was too early to invest and wanted to see if Ali could get physicians signed up to participate.

“While we didn’t gain an investor, we gained a supporter, which is invaluable to us,” Ali said via email.

So far, Bialecki and Hallen have funded five ex-Klaviyos. They’ve even set aside office space at company headquarters near South Station for alumni to work on their new ventures.

It’s not uncommon for a boss to back a former worker in the Boston tech scene. But the checks typically go out after a company is acquired by a bigger firm and key employees, including bosses, move onto other ventures. For example, the founders of Toast, which sells technology to restaurants, got money from their old boss after their company, the Cambridge software firm Endeca, was acquired by Oracle in 2011.

What makes Klaviyo unusual is the founders back ambitious employees while still running an independent and fast-growing public company.

So, why not try to hold on to these entrepreneurially minded employees? Hallen said the company wants to give employees enough autonomy to build new products inside Klaviyo and does what it can to retain them.

“We’d rather have them here,” he said. “But if somebody is leaving to start something, it’s exciting. We want to pay it forward.”

Scott Kirsner can be reached at kirsner@pobox.com. Follow him @ScottKirsner.