60 pitches in 90 days. A Series B term sheet that collapsed. A $15M valuation hit, and she still came out on top.
In this episode, Jennifer Henderson, founder of Colorado-based HR tech startup Tilt, breaks down exactly what it took to raise over $30 million in venture capital while balancing motherhood, market crashes, and investor whiplash.
Jen shares how Tilt was born out of personal trauma, why she built a leave management platform with empathy at its core, and what every founder, especially women, needs to know before walking into their next pitch.
From Techstars to term sheet disasters, this is the real story behind startup success in today’s market.
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Here's what you're in for:
00:00 – “I don’t come from money”: Why Jen chose venture
04:21 – Building Tilt from personal pain
06:08 – Sales tactics that worked
09:07 – How Techstars changed the fundraising game
11:53 – Raising Series A: Saying no to ‘cute’ term sheets
18:03 – Series B nightmares: exclusivity traps, errors & resilience
33:07 – The truth about AI in HR tech
39:02 – Advice to female founders: “Be successful. We need you.”
42:56 – Surviving the current startup market
ABOUT JENNIFER HENDERSON
Jennifer Henderson is the founder & CEO of Tilt, a Colorado-based HR tech platform that simplifies and humanizes leave of absence management for modern teams. After two traumatic parental leave experiences, she turned her frustration into a mission. From Starbucks barista to corporate leader to raising $30M+ across five rounds, Jen's journey is a masterclass in resilience, grit, and founder-first leadership. Tilt is now a trusted solution for teams across the U.S., navigating complex leave policies with care.
Connect with Jennifer on:LinkedIn: https://www.linkedin.com/in/jenniferhendersonjctcjcdcEmail: hello@tilt.com
ABOUT JASON
Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.
You can reach out to Jason through:
Email: jason@thunder.vc
LinkedIn: https://www.linkedin.com/in/jasonrkirby/
ABOUT FUNDRAISING DEMYSTIFIED
Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcas
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