How Jennifer Henderson Had 60 Pitches in 90 Days and Raised $30M

How Jennifer Henderson Had 60 Pitches in 90 Days and Raised $30M

Publish Date: June 5, 2025

Episode URL: blog.thunder.vc/jennifer-henderson-60-pitches-90-days-raised-30m

Video URL: https://youtu.be/q_ujeEuVsjo

Episode Description

Jennifer Henderson, CEO of Tilt, shares how she raised $30M after 60 pitches in just 90 days. From being a first-time female founder to navigating growth during COVID-19, Jen discusses the emotional and tactical rollercoaster behind her fundraising story—and what founders, especially women, need to know about winning capital and scaling HR tech today.

Full Transcript

Jason Kirby (00:00.112): in case anything comes up. The main purpose of our team will cut this all up and get it all dialed in for us. But we'll record for pretty much the full hour. We'll try to stop at the end of the hour in case you have something coming up. And then are there any questions for me before we get started?

Jen Henderson (00:21.218): Ready to go.

Jason Kirby (00:23.411): And you guys, I think you reached out originally following our newsletter, correct? How'd you find out about our newsletter?

Jen Henderson (00:30.339): Yep.

Jen Henderson (00:33.646): I subscribed years ago. I couldn't even tell you where I originally found it. Yeah, it would be interesting to actually look at the subscription date. I'm sure you have that in your CRM probably. Yeah, let's do it. Where did I find Jason Kirby?

Jason Kirby (00:42.482): Yeah, actually, yeah, let's take a look at that. That sounds fun.

Jason Kirby (00:52.196): So that's me the... here we go. And was it, guess where we always subscribe from your tilt email? Yeah, that's okay.

Jen Henderson (01:03.498): No, we used to be Career Allies. That was our first file. Actually, it's still our legal structure.

Jason Kirby (01:13.682): So looks like you subscribed March, 2024.

Jen Henderson (01:18.126): Yeah.

Jason Kirby (01:21.650): Is that something about right or were you following before then?

Jen Henderson (01:25.550): I was probably following before then, but like I said, I was under Career Allies, Inc. But I, yeah, it would probably be helpful, right? If I knew where I found you, you'd like to meet me.

Jason Kirby (01:35.154): I got Career Ally DBA Tilt. Let's see.

Jen Henderson (01:40.364): Yep. That's us.

Jason Kirby (01:43.026): I know it came up, it's still the same email. So one contact. If I can find it... yeah, it looks like maybe you reached out to one of our partners, Interplay Ventures. And I think that's how we got originally connected.

Jen Henderson (01:47.181): Okay.

Jen Henderson (02:01.184): What was the name of the venture fund?

Jason Kirby (02:03.122): Interplay Ventures.

Jen Henderson (02:05.189): Let’s see...

Jason Kirby (02:08.251): So we— they’re investors in us and we work very closely with them. Came out of their boundary.

Jen Henderson (02:10.894): Yes. Yeah, Caroline was one of my contacts there. Caroline and Mark.

Jason Kirby (02:16.882): What was that? Yeah, Caroline. And then— can you share who you raised money from?

Jen Henderson (02:25.288): Yeah, all of them. Our cap table is actually, I would say, pretty small. And they're not well known. So I've never looked to raise from our, you know, the blue chip funds. The fund that led our Series B is named Bramal...

Jen Henderson (02:27.105): Bramall Ventures. They're out of New York. And then we have an early-stage fund called XFactor Ventures, which is out of Boston. And a couple angels. And that's about it.

Jason Kirby (02:42.372): That’s a tight group. Did you know from the beginning how many people you wanted on your cap table, or was it more organic?

Jen Henderson (02:51.473): Definitely organic. I didn't even know what a cap table was when I started. I had to learn it all fast. When you’re a first-time founder, especially a female founder, you just get thrown in and you figure it out.

Jason Kirby (03:05.648): And did you ever get close to giving up during that fundraising sprint?

Jen Henderson (03:12.267): Every single day. I mean, 60 pitches in 90 days—it’s exhausting. But the mission behind Tilt was personal. I experienced the pain of navigating leave firsthand. That’s what kept me going.

Jason Kirby (03:30.711): Do you remember what finally got you over the line?

Jen Henderson (03:35.529): It was a fund that just immediately got it. They didn’t need me to explain why leave matters. They had experience with it and saw the opportunity. That felt different. That was the turning point.

Jason Kirby (03:50.102): I love that. And the traction you had by then?

Jen Henderson (03:55.476): We had signed our first few customers and had growing interest. COVID ironically accelerated the demand for what we offered—companies suddenly realized how unprepared they were for supporting leave.

Jason Kirby (04:11.117): That pandemic tailwind—you had to be ready to catch it though.

Jen Henderson (04:15.632): Yes. We were already doing the work. We didn’t pivot into leave—we were built for it. That’s what helped us scale when the market finally caught up to the need.

Jason Kirby (04:27.499): Have you seen the perception of leave change in the eyes of HR buyers?

Jen Henderson (04:35.732): Totally. It used to be reactive—"we’ll figure it out when someone goes on leave." Now, companies want proactive policies. And they’re looking for partners who can help operationalize it, not just consult.

Jason Kirby (04:49.876): And what about AI? Everyone’s talking about AI in HR tech right now.

Jen Henderson (04:55.311): It’s complicated. Buyers are skeptical of AI-only products. They want human-centered tech. We use AI behind the scenes but never remove the human layer. Empathy is everything in leave planning.

Jason Kirby (05:08.429): It’s wild that we’re still in an era where AI has to be hidden to be trusted. But that’s a real founder insight—tech enablement without removing empathy.

Jen Henderson (05:18.924): Exactly. You can’t outsource care. That’s what leave is about—care. You lose that, you lose trust.

Jason Kirby (05:26.780): How has your leadership changed across these different stages—bootstrapped to venture-backed?

Jen Henderson (05:35.127): I’ve become more confident asking for help. Early on, I felt I had to have every answer. Now I know my job is to ask better questions and hire people smarter than me.

Jason Kirby (05:48.313): That’s a great CEO unlock. Did that shift affect your fundraising conversations too?

Jen Henderson (05:55.732): Absolutely. Investors sense when you’re posturing. Authenticity became my edge. I was clear on the mission, honest about the gaps, and open to collaboration. That resonated more than a perfect deck ever could.

Jason Kirby (06:13.014): If a first-time female founder is listening right now and just got her 20th no—what do you want her to hear?

Jen Henderson (06:20.825): That it’s not about you. VCs say no for a million reasons that have nothing to do with you or your business. Keep going. Focus on building something great. Success is the best way to pull more women into this ecosystem.

Jason Kirby (06:37.440): Hell yes to that. And the best way listeners can support Tilt right now?

Jen Henderson (06:42.192): If you know an HR or people leader struggling to manage leave, send them to ourtilt.com. Or just tell them leave doesn’t have to be chaotic—we can help.

Jason Kirby (06:52.587): Jen, this was awesome. Thank you for sharing all of this and for being real about what it takes. I know it’ll resonate with founders going through it.

Jen Henderson (06:59.442): Thank you for creating space for these stories. We need more of that in tech.