Latest / $100M Exits with Jason Kirby

EP 88: How a Broken Leave Policy Led to a $30M HR Tech Startup w/ Jenniffer Henderson (Tilt)
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…
The skinny
The skinny isn't ready yet — notes appear once the transcript is processed.