Ep. 241 - Jennifer Henderson, CEO and Founder of Tilt on Reimagining the HR Leave Process and the Startup Journey

Inside Outside

On this week's episode of Inside Outside Innovation. And we sit down with Jennifer Henderson, CEO and Founder of Tilt, Jennifer and I talk about Tilt's startup journey and helping companies reimagine the HR leave process, as well as the trends, challenges, and opportunities companies are facing in this dynamic new world of work. Let's get started.

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Interview Transcript with Jennifer Henderson, CEO and Founder of Tilt

Brian Ardinger: Welcome to another episode of Inside Outside Innovation. I'm your host, Brian Ardinger and as always, we have another amazing guest. Today with me is Jennifer Henderson. She is the CEO and founder of Tilt. Welcome to the show.

Jennifer Henderson: Thanks for having me. I'm excited to chat today.

Brian Ardinger: Hey, I'm excited to have you on the show as well. We met through, I think the Rocky Mountain Venture Club and Nebraska Angels and Tilt is an amazing company. I'm very excited to be a part of having this conversation with you. It's in the HR talent tech space. And it's re-imagining leave management to help companies with retention and streamlining their processes, helping with compliance, but to think you called it, bringing the human back to leave.

How about you tell us a little bit about the Tilt story. How did you conceive the company and how did it get started?

Jennifer Henderson: Yeah, sure. The origin story for Tilt. Not that unique, I'm sure to a lot of the other guests that you have that have founded a company. It was completely born out of personal experience. So, my past life was in corporate America.

I worked for 15 years in Fortune 500 companies and I loved it. I absolutely loved my career. I gave everything I had to it. I got very accustomed to promoting every two years and being the go-to person and being in the top of the nine box. Really just got comfortable sitting at that proverbial table, so to speak.

And then I got pregnant and overnight everything changed. I wasn't that person anymore. And that was devastating to me and frustrating to say the least. So, at the time stage of my career, I really turned the other cheek and kept moving forward, you know, clamoring my way back up the ladder. And then five years later, different company, different stage of my career I became pregnant with my second.

And this time I actually had a promotion rescinded. So that was enough for me to say this isn't right. I don't quite know yet what the solution is, but I do know that I just can't turn the other cheek again. So, I founded Tilt four years ago. Again, not really knowing what the solution would look like at that time, but we've done all your necessary stages of a startup: iterate, MVP, beta tests, listen to users, see what sticks, and here we are.

Brian Ardinger: So, moving from that corporate world to the startup space, how did you start adapting to the fact that you were moving from, you know, that exploit stage working in a company that knew its business models were on that certain kind of path. Versus jumping into a startup environment, which is much more in the exploration phase, where pretty much everything is uncertain and unknown. Talk me through how that process went for you.

Jennifer Henderson: Very humbling is how that process went. I felt pretty competent in my business acumen, my ability to build a team, my financial acumen, kind of everything that comes with to your point of more put together and structured organization. Turns out that doesn't all translate, and the world of entrepreneurship has been a very, yeah, I just I'll use the word again, but humbling experience to know that it's not a translatable and, you know, this worked here, so it's going to work there, type of a scenario.

I actually used to in interviews say, Oh, dealing with ambiguity is one of my towering strengths. I didn't even know what ambiguity was until I entered this world of entrepreneurship. It is a whole different world. The short answer to the question, it was a very, very jarring transition and I was not ready for it. And I've spent four years adjusting and learning and throwing myself into doing work different as an entrepreneur.

Brian Ardinger: Are there particular resources or hacks or things that you've learned along the way that you would recommend to those early-stage founders going through the same thing?

Jennifer Henderson: Yeah, it's a great question. My road to competence in entrepreneurship was just leaning into every free webinar, resource, book, person, who back in the day that we could sit and have coffee would have coffee and teach me. And I really leaned into one of my early leaders, told me to be a sponge. And I love that advice. And I really truly like embodied that and tried to soak up, who's done this before, what lessons have they learned? And how can I learn from that?

I think structurally I'm a big fan of Brad Felds. So, I love really all of his books, course works, podcast interviews, et cetera. I think he speaks in a very accurate and real translatable way to being an entrepreneur.

Brian Ardinger: You just went through the Techstars workforce development cohort and congratulations on getting through demo day. What's that journey been like going through Techstars program and more importantly, I think, what do you see the journey is post demo day?

Jennifer Henderson: Well, I got into this program with Tilt after four applications. So, we tried four times to get into Techstars. It's been an aspiration of us as a company for quite some time for a lot of reasons. Most notably, it is very high on the brand recognition spectrum in terms of validation of coming out of Techstars as a graduate.

And that was something that we wanted quite honestly to have on our resume. So to speak is a Techstars alum. And, you know, hindsight 2020, everything happens for a reason. This was the first cohort of the workforce development track in the Techstars ecosystem. And it was absolutely meant for us. Right. We had 11 other brilliant companies around us that were either selling to the same customers or fighting the same ecosystem battles. And it was just a lot of great synergy going through that program.

Everything that we would have hoped for and more in terms of plugging into the Techstars network, having the validation of being an alum, as well as the content, I was very firm in that I wanted our organization to have a strong foundation of all of the components of building a scalable and sustainable startup.

And I mean, you really can't look to much more tried and true than Techstars to get that type of a foundational acumen. So that was delivered. And then some. And then to answer your question and where we go from here, we have a lot of great tailwinds, both internally and externally in terms of the problem that we're solving at Tilt.

And coming out just this week as a grad of Techstars, we plan to continue that momentum through the network connectio...