Childcare is essential for high-functioning societies—linked to better health, education, and employment outcomes. Yet despite its high social return, caregiving remains undervalued, with the labor—paid or unpaid—falling disproportionately on women. Jaime-Jin Lewis, founder of Wiggle Room, is building the infrastructure behind a more dynamic and durable childcare system. Her tool, Auto-Enroll, simplifies back-end daycare operations, turning a 58-page regulation manual into easy-to-use workflows that help small providers stay compliant—and stay open.

Jaime-Jin’s journey to Wiggle Room began long before she ever wrote a line of code. Raised in the racially segregated South by a mother who ran a preschool out of their church basement, care was embedded into the fabric of her childhood. From organizing casseroles for neighbors to vacuuming tiny chairs after school, she grew up in a world where caregiving wasn’t just labor—it was love. That perspective stuck with her and resurfaced in full force during COVID, when she launched Workers Need Childcare, a hotline and mutual aid network that matched families with emergency caregivers during the chaos of school shutdowns.

Now, Wiggle Room is tackling the other side of the care equation: empowering providers. Jaime-Jin shares how she cold-called 6,000 home-based programs in New York City, listened deeply to what they needed, and tested every feature with her toughest user—her mom. With 100% adoption across 65 current daycare sites, Auto-Enroll is already transforming how providers and parents navigate care. She pitches her work to Jin-Soo Huh, partner at The Learning Accelerator, and together they explore what it means to scale trust-based technology, expand across state lines, and stay grounded in community-led design. They also dig into pricing strategy, long-term sustainability, and the power of building with users, not just for them.

Episode Highlights:

02:46 Jamie Jin's Background and Influences

07:45 Birth of Wiggle Room

09:08 Challenges and Solutions in Childcare

14:52 Developing AutoEnroll

19:05 Pitching to Jin-Soo Huh

29:17 Final Thoughts and Takeaways

Links & Resources:

• Jaime-Jin Lewis
• Wiggle Room
• Jin-Soo Huh
• The Learning Accelerator 

About the Host, Nicole Jarbo:
Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun.

About 4.0:
4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.

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