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

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.

Inside Outside Innovation is podcast to help new innovators navigate what's next. Each week, we'll give you a front row seat into what it takes to learn, grow, and thrive in today's world of accelerating change and uncertainty. Join us as we explore, engage, and experiment with the best and the brightest innovators, entrepreneurs, pioneers, and businesses. It's time to get started.

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 connections that we made, through the board additions that we made, and really go heads down for 2021 to prepare us for our Series A. You know, that's a whole new world. And, and right now we're getting that perfect product market sales market fit so that we can just pour fuel on that fire.

Brian Ardinger: And that's a great segue because I wanted to talk a little bit about that product building aspect of the business. You know, especially at the early stages, I think a lot of people, when they hear stories, they talk to founders and everything's been built and, you know, you hear the war stories, but not often you hear the stories of like, what's it like right now when you're in the process of determining and evaluating which particular features to build, or how do you build out your product? 

So, can you walk us through a little bit about your product building approach and what's working and how's it going? 

Jennifer Henderson: Yeah. I think one of the benefits of starting this out with very little capital, we, we bootstrapped for three years before we took a very small angel investment to get those couple early adopters. So, the benefit of that is that we didn't build anything unnecessarily because we couldn't afford it. 

So, the adage of building a staircase to nowhere has never been a part of my product map or strategy in that if we're going to build a feature, we've figure it out on the backend, the high friction solution, we've done it pen to paper, we've done it manually to know this is where the automation needs to go. 

While that is painful at times, and certainly my team would say we probably waited too long for some feature development, it's what I believe the most fiscally responsible way to build out the product so that we know that when we're building an automation in a step or an integration, that number one clients are asking for it, or our team has demonstrated the business case essentially as to why it's going to impact, you know, and I'm talking minutes saved or reduced complexity steps. 

I mean, we're measuring these types of things in the product roadmap down it's minutes. And that's been the methodology to this point that will likely continue to be the methodology, caveat being is that we're bringing in our first senior product owner, senior designer and that individual having really a whole new world view to bring to the next evolution of the product. I just, I can't wait. That's going to be a game changer for us. 

Brian Ardinger: I'd love to talk a little bit more about the customer discovery process and how you actually work with customers on that. Obviously, you came to this idea, basically being a customer and understanding the pain points in that. So how do you incorporate customer discovery into your process? 

Jennifer Henderson: It's integral and it'll never go away. It's the fabric of what we build and how we build it. And it's evolved through the four years meaning, you know, back when I call it my analog days of pen to paper and my predominant network being an enterprise, that was just a lot of discovery interviews. Like what is the pain point at its most basic level. Pie in the sky, what's the most perfect scenario in terms of a solution you can imagine.

And then building and iterating and getting enough data to pull the trigger, so to speak. And from here, you know, we are, luckily we're in a solution that has a service element built in. So, we have a very strong connection to our users inherently in the, in the solution that we're providing. So those feedback loops are already very tight and we're able to get those real time feedback product development asks continually. 

And then it's really internally with the team, how are we categorizing those? How are we quantifying those? What is the qualitative and quantitative components of those asks? And then really in 2021, looking towards putting more, even more rigor around getting user groups stood up and actually having more of a formulaic approach to that type of a product dev.

Brian Ardinger: So, let's talk a little bit about the results and what are some of the case studies or things that you're seeing that are really resonating with your customers. And, and where's Tilt really expanding and going forward?

Jennifer Henderson: This is where actually my 15 years in industry does bring some support to what we're doing today, in that I feel very passionately about ROI and what the results to your point, our clients are seeing. The top of the ladder, no question about it, is retention. So, when we're able to look at pre-Tilt or doing leave without Tilt, we know 40% of women in particular fall out of the workforce after having a child. And that's only one part of the leap support that we provide. But in terms of comparative analysis, it's compelling. 

So, 40% attrition and then post leave, we've had almost 200 leads go through our program. Majority of them being parental of some sort, and we've had 100% retention through our program. So, it's, something's working. The recipe is working. And then quantifying that for our clients to say, we know the cost of turnover, we know what to the dollar is saving you.

And when you look at the current world of work today, even more of an amplified emphasis on employee engagement, employee wellbeing, definitely retention in this world that we find ourselves in. And then from there, you know, those other ROI measures around administrative savings. So, we've quantified a 90% administrative saving for our HR users. Which is also very easy to quantify. 

And then the third layer, I really point to as more of an insurance policy, we have built the entire product to be compliant with all of the different lead legislation that spans the U.S. And that is changing literally by the day. So, there is a kind of a set it and forget it value prop that we're able to give to our companies to say, we know when New York paid family leave has changed the amount of weeks that they're requiring you to have, it's built into the tech. 

You will automatically be alerted any adjustments to your leave policy will be recommended to you in terms of like a plug and play. So those are the three big value adds and quantifications that we've provided our clients and continue to build more rigor around.

Brian Ardinger: I'd like to dig a little bit more into the trends that you're seeing in this talent tech space. I just read a report today that said a quarter of employees are planning to quit post COVID. And so, you're seeing this massive reshuffling of the deck. You're moving, you know, from remote work. And then you're going to have this second shift from all remote to this hybrid. So, what are your thoughts on some of the trends that you're seeing and, and how the world of work is changing? 

Jennifer Henderson: We may have actually read the same article. I love the way that they coined it. There's a tsunami coming. And the way that we at Tilt have really watched this phenomenon continue to evolve with the last almost 12 months, is an acceleration in our opinion of 10 years of conversations happening right now.

And what that means is that companies are no longer able to ignore some of these expectations that employees have asked for, and are now demanding, and they're demanding it by walking out. And that is in our world, very exciting, because we are a new benefit. We are turning leave on its head. We are doing something that has been done in our opinion, very antiquated to this point.

So that shuffling of the deck, so to speak, is incredibly exciting for us. And in our opinion, is it's just the beginning. This is not a just now, and we're going to settle back into a norm type of a phenomenon. This is a, as I said, accelerated the conversations companies who don't choose to deploy, a new way to support their employees will be left behind in our opinions. No question.

Brian Ardinger: And it's not just supporting the employees. It's, it's the, like you said, the compliance not around that has changed. And you know, when you have workforce that can work from anywhere, the companies themselves are put in a different type of environment that they could control before. You know, if you're going, everybody's going to work in Colorado, everybody's going to work in Nebraska. It's a little different when that's spread out all over the world and you've got to comply to that as well. So...

Jennifer Henderson: A hundred percent. 

Brian Ardinger: Do you have any go-to tools or resources or hacks that you can recommend to other fellow founders or product builders out there that would be helpful? 

Jennifer Henderson: Well, I'll answer this from two different veins. So internally our favorite tools as a team at Tilt, we live in Confluence. So that's our chosen methodology within the organization. In addition, we're recent clients of Front, which has been an amazing collaboration tool for our client success team. So, I'm a big, big fan of that organization, and excited to bring them on board.

I think if I answered the question more from a, how are we continuing to evolve and become better as an organization? You know, our company, we are 15 strong now, looking to double if not triple that by the end of 2021. So, with that comes a lot of moving pieces and a lot of changes to how we're doing things, somewhat by the day.

So, myself and my leadership team, we really lean into OKR methodology, making sure our KPIs are very clear that with all of that change, we keep our North star front and center making leave suck less. And that we grow into this larger team with that as our main reason why we get up and do this every day. You know how that manifests itself continues to be a moving target in terms of all hands and stand-ups and things like that.

But yeah, we have an amazing culture doc, that hats off to our COO Kate Feeney, developed for us. That culture doc lays out very clearly who we are, why we're doing this and what we're all aligned to do in terms of values. And we use that as a touchstone very frequently.

For More Information

Brian Ardinger: It sounds great. And I want to really thank you for coming on the show to talk about not only what you're seeing when it comes to the trends in this world of work but giving us some insight into what it takes to be a founder in today's world. And I really do appreciate you come on Inside Outside Innovation. If people want to find out more about yourself or Tilt, what's the best way to do that. 

Jennifer Henderson: Yeah, we can be found at the URL, ourtilt - O U R tilt.com. 

Brian Ardinger: Jennifer, thank you very much for being on the show. 

Jennifer Henderson: Yeah, thanks for the chat, Brian. I really enjoyed it.

Brian Ardinger: That's it for another episode of Inside Outside Innovation. If you want to learn more about our team, our content, our services, check out InsideOutside.io or follow us on Twitter @theIOpodcast or @Ardinger. Until next time, go out and innovate.

FREE INNOVATION NEWSLETTER

Get the latest episodes of the Inside Outside Innovation podcast, in addition to thought leadership in the form of blogs, innovation resources, videos, and invitations to exclusive events. SUBSCRIBE HERE