Personal tragedy made Care.com CEO Brad Wilson a more empathetic leader—and more tolerant of risk

Hello and welcome to Modern CEO! I’m Stephanie Mehta, CEO and chief content officer of Mansueto Ventures. Each week this newsletter explores inclusive approaches to leadership drawn from conversations with executives and entrepreneurs, and from the pages of Inc. and Fast Company. If you received this newsletter from a friend, you can sign up to get it yourself every Monday morning. 

In January 2023, Brad Wilson had begun interviewing for a coveted position—CEO of the online caregiving marketplace Care.com—when his family received devastating news. Wilson’s wife, Ashley, was diagnosed with stage 4 kidney cancer. The couple, whose children were 10, 12, and 13 at the time, decided he should continue pursuing the role. Wilson says they believed, based on conversations with physicians, that Ashley had years to live. “We said, ‘We’re going to show the kids that we’re living, we’re fighting, and we’re going to work through this,’” he recalls. 

Finding a way through

Wilson, who became CEO of Care.com in June 2023 after holding senior roles at HBO, Disney, Lending Tree, and Travelocity, says he had a long-standing connection with Care.com’s mission. As he navigated his wife’s illness, Wilson developed an even deeper understanding of the needs of the families using the company’s platform. He had to manage Ashley’s medical appointments and their kids’ calendars. He built lists of pediatricians, dentists, and teachers while leaning on friends, neighbors, family members, and caregivers sourced through Care.com for household support, especially when he had to travel. 

After Ashley died in 2024, 14 months after learning she had cancer, Wilson says his personal and professional outlook changed markedly. He describes himself as “leaning more and more into faith,” noting that his wife “was not once without faith, to the very end.” He says he cherishes time with friends and focuses on being present for his children. He’s also been emboldened: “I am not afraid to take risks, and I definitely couldn’t have said that 10 or 15 years ago,” he says. “What’s the worst thing that can happen? You’ve got today, so you might as well do something with it.” 

Wilson says he still feels guided by Ashley’s support and strength. “Even today, I find comfort through her,” he says. “I don’t fear or have much angst [about] many of the little things we all worry about on a daily basis.”

Becoming a power user

Wilson says his experience as a Care.com power user has helped influence changes to the product. Founded in 2006, Care.com initially focused on pairing families and individual caregivers. The company, which was acquired in 2020 by Barry Diller’s IAC (now People Inc.) and sold earlier this year to the private-equity firm Pacific Avenue Capital Partners, also offers senior care, pet sitting, housekeeping, and tutoring. Its CareBenefits business lets companies offer subsidized care options to employees. 

Under Wilson’s leadership, the company has enhanced verification for both families and caregivers, along with the recent launch of in-app video interviewing, which lets families and caregivers assess fit before meeting in person. The company has also begun extending backup care—a popular part of its offering to employers—to consumers, something Wilson says he has personally needed multiple times as his own children’s schedules shift week to week. 

Wilson has become an advocate for caregiving policy in boardrooms beyond his own. He notes that a provision in last year’s federal tax legislation raised the employer tax credit for care-related benefits, and he encourages other CEOs to factor that into how they evaluate the cost of offering care benefits to employees. 

For Wilson, the zeal with which he’s working to execute Care.com’s mission isn’t just about creating value for the company’s new owners, nor is it about proving his mettle as a CEO—it’s about memorializing his wife. He says he always wants people to know Ashley was the strongest person he’s known. “Part of the way I honor her every day is to really just attack this thing,” he says. 

Strength from adversity 

Have you experienced a personal hardship that has shaped the way you lead or build products? Please share your stories with me via email at [email protected]—let me know if you’d rather remain anonymous—and we’ll publish examples in an upcoming newsletter.  

Read more: leading with empathy 

• Leaders don’t need to choose between empathy and efficiency  

• Artificial empathy will change work and life 

• How leading with empathy is a competitive advantage to companies