Amy Kiska and the Myth of Perfect Timing
Amy Kiska has always been willing to bet on herself. Growing up in Metro Detroit, she didn’t just dream about working in fashion; she knew she would. She worked toward it with focus and intention and learned early that presentation matters, not as performance, but as preparation: showing up ready, confident, and clear about what you bring to the table.
As a teenager, before she even enrolled at Parsons School of Design in New York, Amy set her sights on Christian Louboutin. Turned down initially due to a lack of retail experience, she found another way in—offering to work for free for a day at Steve Madden to prove her value. It wasn’t bravado so much as self-knowledge; a clear sense of what she could do, even if others couldn’t yet see it.
That instinct, paired with discipline and persistence, eventually led her back to Christian Louboutin, where she spent more than a decade growing from boutique roles into global leadership positions. For Amy, the brand became less a symbol of luxury than of standards that included precision, pace, and attention to detail.
The work was demanding. It involved constant travel, long hours, and the pressure to scale a fast-growing global business, but it was what she loved: the problem-solving, the urgency, and the satisfaction of watching systems take shape around her.
Years later, when Amy joined Infarm during the early months of the pandemic, that appetite for intensity mattered again. The company was growing rapidly, the world felt unstable, and little seemed certain. It was there that Amy met her future co-founder, Molly Morse, and where the earliest ideas for the platform that became Recess began to surface. Parents around them were scrambling for care during school breaks, in-service days, and unexpected closures. The problem became impossible to ignore, and the idea for Recess began to take shape.
What followed was not a carefully timed leap, but a series of events Amy hadn’t planned for. Now six months pregnant, the startup she was working for at the time shut down and her maternity leave disappeared. The stability Amy assumed would exist as she prepared to become a parent was suddenly gone.
Undaunted, Amy invested her own savings and became a co-founder of Recess. Ten days after giving birth, she took her first fundraising meeting. She was prepared, clear, and held deep conviction about the problem she was solving.
Fundraising sharpened her instincts. Some investors had difficulty grasping the problem Recess was designed to solve, particularly those without firsthand experience as parents—or an awareness that the kids’ activity space is a $40B industry.
Others questioned whether the moment was right. Amy paid attention to who understood immediately and who did not. She chose partners who recognized the urgency and parental need for care infrastructure.
As Recess evolved, its mission became even more focused: helping parents find and book reliable care on school holidays, no-school days, and unexpected closures. By working directly with providers, Recess has helped create new program offerings, expand access for families, and support the small businesses that care for children. Now live in Austin, Texas, Recess is expanding statewide this year, with national growth on the horizon.
Amy Kiska doesn’t believe in perfect timing. But, by showing up ready to work—even when the ground is shifting—she’s helping change how families navigate care, and how companies can be built around real, lived problems.