Why Most Founders Fail at Series B
(And How Tilt Didn't)
Jennifer Henderson didn’t set out to be a founder; she just got mad enough to build something no one else would. In this episode, she breaks down how she turned two traumatic parental leave experiences into Tilt, an HR tech company that’s now raised over $30M. From pitching 60 times in 90 days to getting blindsided by a term sheet that knocked $15M off her valuation, Jen doesn’t hold back. It’s raw, real, and a great story founders need to hear, especially if you’re navigating this market and wondering if the pain is worth it.
Check out:
- 00:00 – “I don’t come from money”: Why Jennifer 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:
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