March 2, 2023

Episode 191: Jen Henderson, Founder & CEO at Tilt

Jennifer Henderson is the founder and CEO of Tilt, a company revolutionizing employee leave in the workplace. Tilt’s SaaS platform creates a human experience through technology to support every aspect of a leave of absence. She spent 15 years in corporate America prior to founding Tilt in a variety of operational roles. She lives in Colorado with her family and loves being outdoors.

Julian: Hey everyone. Thank you so much for joining the Behind Company Lines podcast. Today we have Jen Henderson, founder and CEO at Tilt, a company revolutionizing employee leave in the workplace. Jen, I'm so excited to chat with you because not only has your journey been, at a few different company stops and in particular with what you're doing now at Tilt.

It's so interesting because, with remote and and work culture completely shifting and, and obviously post pandemic and companies really trying to make sure that they're offering the most competitive. Benefits or, or environments for employees. I think, offering these other kind of what we thought were an ancillary benefits like time off and things like that have now become as a necessity as, as people are understanding, burnout rates and things along that nature that I would love to get into any statistics that you have.

Of course. But before we get into all that, what were you doing before Tilt?  

Jen: Yeah. Great. Happy to be here Julian. Thanks for having me. My background is corporate America. I spent 15 years in Fortune 500 companies, always in operational roles. And I loved everything about it. I was a self-described career woman through and through and that truly was gonna be the rest of my, my professional career as I saw it until I became pregnant and the tables turned and all of a sudden, yeah, I faced what I was truly naive to understand as what I now know is the mental, the motherhood penalty and career stagnation and yeah.

Really as it relates to what we do today, it all stemmed from a pretty crappy leave experience is how. . Yeah. It's,  

Julian: it's bizarre. You mentioned this, I was just talking to my to my partner a second ago about there's a lot of TikTok information and a lot of talking about the. I, I guess, yeah, I, I've never heard of the, the term motherhood penalty, but it's like the, the, the, it feels almost like, an infraction when you go through a life experience like this and, and then there's all this makeup work and, and it's such a weird experience.

And how could you know, I guess is there any companies out there that are, that are doing a good job at it or that are, are working to learn? And how can most companies just offer a better experience for people in the workplace regardless of. Gender, but when this life experience comes about, especially for women.

Jen: Yeah. I love that question and it's, it's a long answer to a short question in that you set the stage perfectly. The the times are changing and we're thrilled about that, right? Yeah. The future of work, COVID certainly accelerated this conversation in the workplace. We believe by at least five, if not 10, And what we're starting to see is that paid leave benefits are now table stakes, whereas they certainly were a premium just two or three years ago.

And what that means for organizations is whether they're in a state that has a paid leave program or not, they are the ones who are having to find ways to financially provide this benefit. And the good news is, is there's a tremendous amount of compelling data and ROI statistics out there as to how financially feasible it.

Because if you lose talent by having an ineffective leave experience, the costs are enormous. Two to three times a salary from an acquisition standpoint, turnover, institutional knowledge loss, and then in this day and age, the reputational damage and risk to litigation is significant. Yeah. So we're seeing companies, number one, table stakes from a benefit stack stand.

number two leave is getting a seat at the table for the first time really in history. So yeah, employers who are progressive in our opinion, are removing gender language, for instance. So parental is, parental is parental. It's not maternity, it's not paternity. Yeah. It's all past to parenthood. And the critical element of it is the utilization of the leave.

The quickest way to gender parody in the workplace is men taking equal leave, if you can believe it. Yeah. So yeah, it's no longer moms need this time off. It's moms and dads. Or Dads and dads or mom, like all of them are the same.  

Julian: Yeah. . Yeah. You mentioned an interesting point, and I think a lot of people debate and argue about, language that's being used and that it doesn't matter.

But I, I'm, I'm on the opposite camp. I really think whatever you say or however you label something really speaks to the, whether it's the motivation behind it or the structure or, or it, it means so much more than just having a name or label. But what does it mean to finally shift the language, not only maternity leave or paternity leave?

Parental leave and, and kind of acknowledging that there, there's, there's time that needs to be taken away from work. What does that shift in language, mean in terms of its, its actual effects. First there's, there's, there's this constant debate about language, but like I said, I'm in one camp, but I, I'd love to hear your response.

Jen: Yeah. . No, I totally, I'm in the same camp as you. So , I think I'm confirmation bias here in that I think it dramatically matters. And even so if you look at some of the legal cases that have been brought to surface over the last couple years, you're seeing this language around primary and secondary caregiver type scenarios.

Yeah. And there's a lot of we believe justifiably disgruntled employees saying, you can't ask me to take a secondary caregiver position. We're we're, we're both. So the language is critical in our opinion, and again, the the cases are starting to dictate the legalities around how outdated it is using that kind of archaic language.

Julian: Yeah, I'm always curious, in terms of, the kind of expectations or I guess, expected amount of time to, to be off. Does it, does it change with gender? Does it change with the company and organization? How do we know, if, if I, I employ different employees and, and how do I know how much time to offer an employee and also how much engagement I, I should have?

Cuz the, the, the other thing I'm thinking about is the ability to. Keep my employee up to date, but also give them that space they need during that time of leave. Um mm-hmm. , but it shouldn't be kind of a cutoff loop and then all of a sudden you get a rush of information when you get back because that just seems inefficient and, and overwhelming.

But I guess I, I know I asked two questions there, but for the first piece, how do I know how to set up benefit paternal benefits for, for my employees?  

Jen: Well, that's a $64,000 question because we're humans, . We're very complex, unique beings. And one of the biggest problems we believe at Tilt with the current state of leave is that it's by and large, a peanut butter one size fits all.

Yeah. And that's just not in fact true. So there is no medical proof, which I think is very interesting, that 12 weeks, which is a typical, if somebody gets parental leave, for example, as one of the leaves that we. 12 weeks is probably what we would say is standard. So three months. There is no medical documentation anywhere that exists that says that's enough time to heal from giving birth or having a cesarean or whatever it might be.

It's just this darted a wall that was created years and years ago that we've adopted and carried through, which is bonkers to me. So I start there to say that there's nothing medically in the world that says this is the amount of time because. Pregnancies are different, births are different ways to parenthood is different.

Yeah. You can even look at the foster parent situation and there's different situations and circumstances there. So what we like to role model it, Tilt and encourage our companies to do is create as much flexibility as humanly possible. . Yeah. So if you, if you offer a certain amount of time, be flexible within that.

Somebody actually may not want to use all of that time or may want to structure it in this, in an intermittent capacity. Yeah. So a month off, two weeks on, two weeks off. And that flexibility really allows people to have the autonomy to build what works for them. Mm-hmm. . And you look to, some of the far more progressive countries in the world, which is basically every other country besides the United States and Papa Guinea.

And you can see up to a year or a year plus, that's mandated. So, I mean, talk about we have a ways to go. We have, we have a ways to go considering we have zero right now.  

Julian: Yeah. Yeah. And what kind of compromises can, we expect in, in this new environment, you say, it's totally understandable to have a year leave and, and cuz it's such a critical time in the development of, of children.

But from, from, From, from obviously the birth to when you return to work, what kind of flexibility have you seen companies or compromises? Have you seen companies and employees? Fine in terms of a middle ground, because as I mentioned a second ago, if I'm an employee having to take, leave off, I don't want to be completely disengaged, but I don't want to say be accountable for anything that's say timely. What are some compromises that you're seeing in the work?  

Jen: It's a little tricky because there are some laws that employers have to comply with in terms of asking for work to get done if someone is on an F M L A designated leave, for example. But we very much agree with your line of thinking at Tilt in that completely severing communication.

Typically hits poorly from an engagement standpoint, and there are certainly ways that employees can stay connected. Their work where they spend so much time of their days and their lives and their weeks, to have that like literally ripped away from them during a time that is probably very emotionally distraught.

Whether they've lost a loved one or they're on a mental wellness leave or whatever type of leave it is. That type of disengagement is really risky in our opinion. So we work with our organizations through our technology to structure way ahead of time. What will that on leave communication plan? And again, that needs to be specific to the person, the company, the manager, the leave, all of these intricacies, but giving that authorship to what works.

And for instance, we have at Tilt when we have somebody go on a leave in a vice president capacity, which was recently, they wanted to be made aware of any changes on their team. So if anybody left or was hired or whatever that might be. So we systemically went through and said, what is a texting scenario and what is not a text scenario.

Yeah. It's as simple as that. It's just communication.  

Julian: Yeah. Yeah. The communication piece is, it seems so simple, but it, it's, it takes a lot of effort. It takes a lot of work and a lot of understanding on, from both sides of the, of the equation. Tell us a little bit more about Tilt now. Is it just now is it just a, a family leave or is it other forms of leave that are integrated into the platform and what, what has it done in terms of relationship to employees and employers?  

Jen: Yeah, so we are a tech-based solution. We're by definition, HR tech tool. And what that means is that we've created a technology to ingest all these disparate parts of a leave. So again, I mentioned earlier, it depends on what state you're doing your work in. It depends on what size your organization is.

Yeah. Depends on what the paid leave or, or lack thereof policy is for your organization. And then a disability. So we have all these different inputs into one particular. That we ingest from the organizations that we support. And then the technology does what it does best, in my opinion, which is codify the workflow.

Mm-hmm. . So if this, bend that for every specific leave so that at the end of the day you have a unique to you guided plan on the before, during, and after your leave. That sits in our Tilt technology. And you have that interface to be able to interact with on your own time in addition to your manager. We know that managers are a very critical element to success of a leave or lack there.

So they get their own Tilt leave plan to be the best that they can be for their employee experiencing that life event. And then the differentiator for us, and we foundationally believe this is a critical element and will exist as long as I am still the CEO of this company, is we have what we call an army of empathy warriors, who are our leave success managers.

And what they're in place for is that we can codify a leave all day long. But we're dealing with humans and the code's gonna break. And the really disheartening part about that is that if you have a caregiving leave that turns into a bereavement leave, or you have a parental leave that turns into the loss of a baby or a pregnancy, there will never be a day where you're gonna get into Tilt and click a button to see what your next steps are.

You will get one of our empathy warriors to help you walk through what's available to you, what your next steps are, how to navigate that. Is critical to the work that we do. As we say, we're bringing the human back to leave.  

Julian: Yeah. And what caused that, I guess injection of that level of, of service Because, as founders, we know how costly it is to offer, we service and obviously there's some pros and cons, there's some benefits, but also there, there's some sacrifice in, in, in terms of the operating model, was that always built into the model and why did you feel it was so imperative to Tilt as, as a company?

Jen: Yeah. It has always been built into the model and every one of the five fundraisers we've done, I've explicitly said my first conversation with an investor, don't ask me to get rid of it. I'm not gonna hate your 90% gross margin number. It's not in our, it's not in our ethos. And so far, we've brought the right people around the table who understand that that is important to the work that we do.

Yeah. And you're actually the first person that has ever asked me why. And it's a very personal story around that. I experienced a miscarriage in the middle of a working day, and my boss couldn't have given two shits about it. Like, it was just like, let's move on and get back on the horse and go back to action.

It was the most cold and inhumane response to an experience that I was having, and I just, in, in hindsight, at that moment in time, yeah, I, I made a commitment to myself. I would never do that to others.  

Julian: Yeah. I appreciate you sharing and that's it's hard to hear the, the, that was the reaction and I think, and I'm curious on, how you feel about the evolution of, of workplaces in that respect.

And it seems like companies are trying to bring more empathy and, and working towards better communication and, and better relationships with their, their colleagues. And how have you seen that improvement or, in honesty, are we still in that kind of I guess ecosystem or environment where, employees life experience aren't , as weighed into their work as they should be?

Jen: I mean, if you figure out the way to make managers better, you, you crack the code. It is the hardest job in the world having done it for two decades. Yeah. It is the hardest job to codify or to give kind of a one size fits all resource to. So I think what we're starting to see in terms of how we show up for manager efficacy is that you really need to make it accessible and self-serve on people's own time.

Meet them where they're at because managers have 25 plates spinning at any given time. Yeah. I've also learned through this process that if you make it self-serve, you remove the stigma from especially tenured managers who think, I've done this for 10 years. I don't need somebody to tell me how to do a leave.

When in fact leaves don't happen every day. Right. And likely there has been changes to legislation and likely there's things you probably don't know. So you remove that ego from the formula of, no, no, I don't need a guided tour here. No, you actually really do. And so they can do that on their own time without people knowing.

And then I would say the third layer of the manager efficacy is that, again, learning how to have that EQ or that emotional quotient or empathy at the forefront to be able to recognize these are all unique and we are trying to give you the ability and the emotional maturity to approach them as a human first.

Right? And with the spirit of the policy or compliance as opposed to the letter of. because that's when things start to get hairy and yeah, it's hard. It's, it's certainly not a one size fits all.  

Julian: Yeah, yeah. Thinking about, fundraising and, and I know, being a first time founder being coming outta the corporate world and, what kind of level of, I guess, structure did you take from that corporate environment that was able to influence Tilt as a company holistically?

Is there a couple of, of. Structural pieces that big companies are doing well that, that you moved over in, in terms of, bringing some, I don't wanna say maturity cause I think there's a connotation there, but, but almost it's, it's like the, the, the companies beyond its years in terms of its infrastructure.

Did, was there anything that you took over in terms of lessons or, or structure from, from larger companies?  

Jen: man, not nearly as much as I thought I could. , yeah. I was very, very humbled in the early years of learning how to be an entrepreneur and still to this day, learning how to be an entrepreneur of what was translatable.

Yeah. Transferable skills. I mean, down to, I could tell you a p and l in my sleep with one eye clothes and a proforma is a totally different animal. Yeah. So it's this kinda yin and yang of, of the business world. But I will say, structurally, I really credit my foundational years in corporate America to understanding the benefit of operationalizing things.

Mm-hmm. and creating structure. When it's necessary. Mm-hmm. . However, in the world of startups I've learned if that pendulum swings too far and you over-engineer a process when you're scrappy and young and in growth mode, it can be very hindering. Mm-hmm. . So it's having these tools in my toolbox, not only knowing when to use them, but knowing how they can adapt to the startup world.

And then the, the biggest transferable skill that I will forever and always be grateful for, that I had my time in corporate America to practice as the people leader. Yeah. And understanding how to coach, mentor, train, develop higher fire, inspire individuals is, is such a foundational rock in terms of what I get to do every day, and that's where I learned it so forever.

Julian: Great. . Yeah. I love, I love talking to entrepreneurs who, who come from, a background in corporate Americ or at larger companies and, and I love to ask that question because I think it, it does almost add a little bit of, of a superpower to, the, the entrepreneur journey with whatever they're building because.

I mean, yours in particular. Building a team is, is probably the one of the top three things that any founders, it's like fundraising, building product, building a team, right? , it's like those three things are what , we fixate on the most, I think. But thinking about, , as a first time founder we always have to ask about fundraising and that whole process.

And in particular, HR software, there's a, a lot of different players in the space. It's, it's almost kind of Red Sea in a lot of ways. And I, I love the differentiating piece. I think. The people component , is, I think over undervalued in a lot of different companies. But during the fundraising process, how, or I guess when was the tipping point?

When was the catalyst? What was the moment where you started to feel the traction was moving in your direction and your pitch was strong enough and you are meeting the right partners? How many found, how many investors do you have to go through? And when did you feel like that moment was kind of clicking for people to kind of get your vision and mission of the  

Jen: I'll tell you if I find it , I I don't know that we have enough time to get into the harried journey of fundraising as a first time female founder. Yeah. In, in this system. It is very, very, very broken. You've had other female founders on your podcast before. Yeah. And there's a reason only 2% of us get venture funding.

There's a very specific reason, so. Mm-hmm. , it has been the. Without question part of bringing this company out of the earth.  

Julian: Yeah. Yeah. And thinking about, so in, in going back to the company, tell us a little bit about the traction you've had over the last couple years and what in particular are you excited about in this next year's growth?

Jen: Man, it has been a rocket ship ride, quite honestly, since March of 2020. Yeah, we came out of the box selling just that quarter before. So the end of 2019. Wish I could tell you I saw what was coming with the pandemic and how that was. Literally lightning fuel for what we do and how we do it. Yeah. So March, 2020 legislation was written here in the US that impacted Covid 19 related leaves.

Mm-hmm. , nobody knew what the hell to do with that, even before the ink was dry on the legislation. So we were in a war room quite literally trying to figure out how to support our small but mighty customer portfolio at that time. And from that point forward, we've doubled in growth every single year. And this year we expect the.

Because what we have going for us, in addition to the altruism and the, and the reason why this needs to be in the world is that the state of paid leave legislation, mm-hmm. is very, very dynamic and states are passing these laws every single year and they're editing them every year and every state is doing it different.

So it has truly become untenable for an HR representative singular, or a team of HR individuals to know everything that's going on in the world of leave, which is why technology is the right  

Julian: solution. Yeah, yeah. What are some of the biggest challenges that Tilt faces today?  

Jen: I think any company, I resonate a lot with the stage that we are at in similar growth stage organizations.

Wrestling between keeping true to who we are as we continue to grow. We have 85 Tilters now, full-time remote, fully distributed team across the us and this elixir or this why we do what we do. This cultural connective tissue is yeah, a complex system. I kind of akin it to a garden. Like you, you have to pull the weeds and you have to water it and you have to check the pH and you just do it on this constant basis.

Yeah. And through a. it is 10 times harder. And we are now, this is my, my, I'm five and a half years into this world and it has not gotten any easier Yeah. To keep that momentum and that excitement alive every day.  

Julian: Yeah. If everything goes well, what's the long term vision for Tilt?  

Jen: Every single person in the world. This isn't just a US problem in the world who takes a leave, the answer is, well, you're gonna use Tilt. Right? It's, it's a common place. It's a household name. That's, that's what happens when you take a leave.  

Julian: I love that. I love that. I always like to, this section I call it my founder faq. So I'm gonna hit you with some rapid fire questions and then we'll see.

So the answers are and see where we get, but what's the hardest part about your job today?  

Jen: prioritization.  

Julian: Yeah. What if, if you weren't working on Tilt, what would you be working on?  

Jen: Changing the 2% of VC funding when the female founders ?  

Julian: Yeah. That's a good one. That's a good another question is any, whether it's early in your career or now what piece of advice has been extremely helpful for you during the entrepreneurial process that you would share with other?

Jen: two of them, two pieces of advice. Get knocked down seven times and get up eight . Just keep getting up. And the second is, I've shared this many times, but I believe it in my bones. If you don't have a visceral connection to the problem that you're solving, if it is not part of your makeup, I don't know how you continue to go through the ups and downs of entrepreneurship.

Yeah. For me, it's not only a very personal story, but I have living, breathing little beings that look at me every morning at breakfast. Yeah. And. A self-imposed deadline until they hit the workforce age to have fixed this for them. So I can't imagine a founder doing this because they just want a faster widget out in the world.

Yeah, it is. It is part of my being.  

Julian: Yeah. Yeah. I love that. I love that. How do you kind of decompress? What are, what's one way or, or a couple ways that you, say take yourself away from Tilt and reinvest in yourself to, to re encourage the energy because it's stressful. You go through ups and downs, you go through challenges.

Even the motivational piece. There's a lot of pressure. A lot of founders go through it. What are some things that you do to kind of decompress and, and rejuvenate the energy?  

Jen: I had a founder once tell me that until you're in a bathtub at two in the afternoon with a bottle of whiskey, you're not really a founder.

And that felt very true to me because I, I really don't think people talk often enough about the mental wellness of founders. It is. Not insignificant and it is not easy, to your point. And some of the coping mechanisms I have is a great therapist. Yeah. And exercise that is a very big outlet for me to keep my head on straight.

And then I've also started to embrace, The ability of checking out. Yeah. And allowing the space in my brain to come up with ideas, whereas before it was how packed can my calendar be? How long is my to-do list? Now I really have reoriented around. I need space to think. And that's intentional  

Julian: now.

Yeah. If you're a wave, a magic wand what's one thing you wish your business could have now?  

Jen: Thousand times more customers. .  

Julian: Yeah. Yeah, yeah. I feel like that I might have to change the question because I feel like most founders are like more customers or more investment, and that's pretty much, those are the two, those are the two kids that, that we sit in.

I always like to ask this next question, not only selfishly for personal advice, but also for my audience as well. Whether it's early in your career or now, what books or people have influenced you the.  

Jen: When I jumped outta corporate America into the world of entrepreneurship, having never stepped foot in this before, I had self-education to do in a big, big way, and Brad Feld was my library.

Go-to anything I needed to know. His books were my, were my Bible. So I love Brad Feld for the entrepreneurial education and we're very honored to have him here in our Colorado ecosystem. Yeah. And then on the culture side of things, which again is my passion and my superpower in the world of work I'm a very big fan of the Nine Lies of Work.

It's a book that was put out into the world by Marcus Buckingham and it runs Affront Any and. Preconceived and, and beat into our brain's way of being that we've had in the world of work for decades that is archaic and doesn't work. Yeah. I can't recommend that book enough. It's a phenomenal book.  

Julian: I love that. I love that. And I, I, another question that comes to mind is where do you go to find your community? Where do you go to find your, your founder community? And, and where do you go connect and, and collaborate and, and communicate? And, founders talk about, it, it's imperative. It's almost not only your lifeline, but sometimes your.

Your launchpad to, to success when, when you're working when you're building a startup, but where do you go to find your community and, and foster that relationship with other founders?  

Jen: Yeah, I haven't fully cracked that nut. We have we're Techstars alums and Techstars is a great community. No matter where you go, there's always Techstars there and great connectors.

But in terms of having a small group of like-minded founders, we don't sit on the coasts. We're not in a heavily concentrated startup city. And to illustrate that, I was part of a founding group of female founders in my local town, and there were four of us, and only two of us remain in the world of startups.

So, wow. It's very, very small. But the nice thing is we all live in a predominantly virtual world now. I'm a part of a group called Leaders in Tech, which is a phenomen. Education group, a 12 long immersive that I've met incredibly brilliant other founders in. So I think you just have to be creative and see what fits for you.

But it's something I'm constantly looking for because that community is critical.  

Julian: Yeah. Yeah. Before you give us your, your plugs, your LinkedIns and, and your websites and everything where we can find and support you is there anything I didn't ask you that I should have or that you would have liked to.

Jen: that's my favorite question to ask other people.

No, I, I've thoroughly enjoyed this conversation. I think you hit on the big rocks. I I typically discourage people who are in interested in entrepreneurship. It's not for the faint of heart, and it's not for everyone. But I will say I have learned more in five and a half years building this company than I learned in 20 years in corporate America. So, It's pretty cool.  

Julian: Yeah. Yeah. I, I love that piece and I agree and not only with, don't do it if, if you don't have the stomach for it, but also the, the acceleration and learning with, with having that ownership of whatever product or service that you have is, I mean, 10 times more of a learning experience than I don't even know what matches it, because of the accountability, the learning curve and, and everything that is associated with it.

The network you build. So beautiful the, the whole journey, and I appreciate you sharing yours. And last little bit, share with us your, your websites, your LinkedIns. Where can we support you as a founder? Where we, where can we view the product? What are your websites? What are your LinkedIns? What are your Twitters?

Where can we find and support you?  

Jen: Yeah. is our site. Come, come visit us. I'm on LinkedIn, Jennifer Hendersen can't miss me. And you were on all the social medias, either the handle Hello Tilt, or hour Tilt, o u r. So amazing,  

Julian: amazing. Jen, it was such a pleasure chatting with you and not only learning about your journey in corporate America, but also how, the, your experience has really pushed this momentum into what Tilt is doing and, and what everyone you know is really, really fighting for, which is the freedom to work, but also have time to, take on their personal life to, to be able to, yeah.

Say balance, the work life balance is. Taking enough time on, on a lot of different aspects of life and, and managing that time well, and it's amazing to see what you're doing and I hope you enjoyed yourself on the show. And, and thank you for joining us.  

Jen: Great conversation. Thanks Julian.  

Julian: Of course.

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