Kate Dilligan spent over $8k to keep her hair during chemotherapy. The process was high-friction, stressful, and unnecessarily complicated. She had a Stanford MBA, a background in tech, and the "fancy job." If the system wasn't designed for her, it wasn't designed for anybody.
So she did what founders do: she built the solution herself. Cooler Heads makes scalp cooling therapy, allowing chemotherapy patients to preserve their hair, broadly accessible. Kate calls it giving patients back their privacy, agency, and identity. Because when your hair falls out, everyone knows you're sick. And sometimes you just want to be Kate the tech executive, not Kate the cancer patient.
When Jill and I talked with Kate, we heard what it looks like to build work that matters from the deepest kind of personal experience — and how to carry that weight without letting it break you. Here are three things we learned.
Cooler Heads gives chemotherapy patients back their privacy, agency, and identity. What does that actually mean? If you have hair and it suddenly goes away, everyone asks: "Are you sick? Is your partner sick? Why'd you shave your head?" Whether you're at work or a social gathering, you're constantly barraged with questions. And you don't always get to choose when you want to share that you're going through cancer treatment.
Kate pointed out something we hadn't considered: the burden patients carry trying to make everybody else feel okay about the fact that they're sick. She had to comfort people about her aggressive stage 2B breast cancer diagnosis. "Why is that my problem?" she asked.
Within the first week of Kate's diagnosis, she knew the healthcare system wasn't built with people in mind. She was on I-5, driving into work, trying to schedule an MRI. The scheduler said, "Your insurance hasn't approved it yet, so you just need to agree that you'll be financially liable if your insurance doesn't approve it." When Kate asked how much it would cost, the scheduler put her on hold, came back two minutes later, and said: "Well, it shouldn't be more than $5k." But ultimately, the scheduler couldn’t offer a real number.
When Kate decided to swing for the fences and build Cooler Heads, she did it with a clean sheet of paper. If she was going to invent scalp cooling therapy all over again, how would she do it? She'd eliminate all the friction. She'd make it broadly accessible. She'd center the patient experience.
Kate admitted she had no idea how hard it was going to be. She didn't come from medical device. Some told her: "Great idea, but you don't know what you're doing. You've never sold to a health system." Her response? "Ignorance is bliss." She decided to learn everything she could, surround herself with subject matter experts, and follow the through lines she started to see. And when friends asked, "If not you, then who?" She couldn't argue with that.
Kate's mother died right before Thanksgiving 2014. Shortly after, she had to move her father into memory care because he had Parkinson's dementia. They moved him in after Christmas, the weekend right before the new business year started. That Sunday night, Kate's CEO called. He knew everything she'd just been through, and said: "Kate, the party's over. I need you back."
The party. As if watching your mother die and moving your father into memory care was some kind of vacation. Kate described it as a slap in the face. "I'd been busting my ass for you for a decade. And you're going to say that to me?" That moment cost him Kate's loyalty. And it taught her something crucial about leadership: every single time she's been a little more human to somebody, it has always paid off.
At Cooler Heads, Kate leads differently. She's transparent, especially when it's hard. It took more than a year to raise their Series A, and things got rough. But by being transparent and earning the trust of her core team, she built something rare in startup land: minimal turnover at the top. Her commercial lead, her engineering and production lead — they've been with her for years. She's also a big believer in always having a Plan B and a Plan C. She tells her team: "This is Plan A, this is what we'd like to happen, but if it doesn't, here's our fallback position."
People stay when they're valued, when they believe in what you're doing, and when they can trust you because you're honest about when things aren't going well. Kate understands that because she's been on the other side — and she remembers exactly how it felt when someone treated her like the party was over.
What gives Kate hope about the future of work? That we're figuring out how to make tech work for us instead of working for the tech. She thinks we're in an uneven period right now, but these things are cyclical. And there’s certain things only people can do.
My favorite takeaway came from her bonus answer about her dogs, Opal and Lupita. The lesson they've taught her that no business book ever could? You have to be present every single day. Kate had a dog when she was going through chemotherapy. Guess what? That dog needed to be taken care of every single day. The first weekend after chemo, Kate was sitting in her living room feeling awful, and her golden retriever walked up and barfed on the floor next to her. Kate's reaction? "I went through chemo and now I have to clean up dog puke. Are you serious?"
But that's the point. You have to show up. Even when it doesn't feel good. Even when you just want to sit with your pain. Life, and work that matters, requires you to be present.
Jill and I are grateful Kate showed up for this conversation. And we're appreciative of the lives she's impacted by showing up every day to build something that gives them back their privacy, agency, and identity.
Listen to the full episode of Work Made Human to hear more from Kate Dilligan about the "party's over" moment that cost her CEO her loyalty, why she'd eliminate email as primary workplace communication, and why she learned to pitch Cooler Heads without leading with her personal story.