Entrepreneur of 2023 Finalist — Jennifer Henderson

For Jennifer Henderson, starting TiLT in 2017 was personal. “I spent 15 years in corporate America, always working for Fortune 500 companies in an operational role,” says Henderson, 42. “In the early years of my professional career, I also went through seven years of in vitro fertilization with my husband, trying to get pregnant. Then we got pregnant, and overnight I stopped getting invited to the table.” 

READ: Guest Column — Fighting Gender Politics in the Home Improvement Industry

But that wasn’t the immediate catalyst for TiLT. “Five years later, a different company, a different stage of my career, when I announced I was expecting with our second, I actually had a promotion rescinded,” she says. “That was the straw that broke the camel’s back for me.” 

Henderson thought there had to be a better, more equitable way of managing corporate leave programs. “That’s when I started to lean into solving leave of absence, and quite honestly, when I left corporate America, I was just very pissed off.” 

TiLT’s platform manages paid leave programs for client companies while reducing the risk of both litigation and turnover. The company went to market with its platform in 2019. Four years later, it has 85 employees. 

“We are an HR tech tool, by definition,” Henderson says. “We often point to TurboTax in terms of what they have done in streamlining complexity in a very disparate landscape in a similar way to what we’re doing with leaves of absence.” 

READ: The Best Modern HR Strategies — Navigating Challenges and Embracing Opportunities

Initially targeting California-based tech companies “was very successful,” Henderson says.  “We’ve had at least a 2X every year since coming out of the box and I don’t see that changing this year.” 

After closing on a $10 million Series B in late 2022, TiLT is scaling up to serve large enterprises. Big companies “have very few options to do leave currently, so these large organizations are pulling TiLT very aggressively to swim upstream,” Henderson says. “We’re moving as fast as we can to position ourselves to support anyone from the Walmarts of the world to mom-and-pop, Main Street stores.” 

Henderson says her personal connection to TiLT’s mission has been critical to the company’s success. “I truly believe that if you don’t have a visceral connection to the problem that you’re solving, I don’t know how you manage through the ups and downs that this entrepreneurial journey throws at you. For me, I see my daughter every single day, so I’ve given myself a clock until she enters the workforce to make this better for her, and that’s a hell of a motivation.”

Denver-based writer Eric Peterson is the author of Frommer’s Colorado, Frommer’s Montana & Wyoming, Frommer’s Yellowstone & Grand Teton National Parks and the Ramble series of guidebooks, featuring first-person travelogues covering everything from atomic landmarks in New Mexico to celebrity gone wrong in Hollywood. Peterson has also recently written about backpacking in Yosemite, cross-country skiing in Yellowstone and downhill skiing in Colorado for such publications as Denver’s Westword and The New York Daily News. He can be reached at [email protected]