Jen Henderson of TiLT: “You can’t be what you can’t see”

You can’t be what you can’t see. If we don’t role model being a female founder for future generations, we won’t change the pattern matching. In addition, we know through research that more diverse teams (diverse gender, background, experience) produce better results. If entrepreneurs aren’t comprised of that level of diversity, the evolution in society […]

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You can’t be what you can’t see. If we don’t role model being a female founder for future generations, we won’t change the pattern matching. In addition, we know through research that more diverse teams (diverse gender, background, experience) produce better results. If entrepreneurs aren’t comprised of that level of diversity, the evolution in society will be stifled.


As a part of our series about strong women leaders, I had the pleasure of interviewing Jennifer Henderson, founder and CEO of TiLT, a company revolutionizing employee leave in the workplace. TiLT’s tech-enabled platform manages the entire lifecycle before, during and after leave to help companies stay compliant while retaining top talent.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

As a professional mom with 2 small children, I experienced career stagnation and pregnancy discrimination when I disclosed both of my pregnancies. My employers simply didn’t know what to do with me, or women like me, to maintain career growth with pregnancy and young children. The penalty of motherhood that women incur to ‘choose’ between their career or staying at home with children is antiquated, short-sided and shuts out an immense talent pool that is more educated, experienced and driven than ever before in history. So, in 2017 I set out to figure out a way to fix this problem.

Can you share the most interesting story that happened to you since you began leading your company?

I had an investor tell me that he doesn’t invest in mothers because ‘he needs his founders to work.’ Little did he know, that lit such a huge fire under me to not only prove him ignorant but be a part of changing this bias in case my daughter, and other little girls, want to be an entrepreneur one day.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

My children have been my co-workers many times throughout getting TiLT started. I had a presentation to a group of investors on zoom and my kids had a pretty bad accident in the background (my 3-year-old went headfirst into the fireplace). Of course, I was home alone with them and there is no amount of muting that can help that kind of screaming. The good news- that group still invested!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Dave Harris, managing director of Rockies Venture Club, has been there from the idea stage. He has taught me everything from what a venture-backed vs. lifestyle company is, how to raise, scale and effectively present our work. He’s been our unwavering cheerleader when others weren’t believers and I hope every entrepreneur gets their own Dave Harris.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Money. There is a significant difference in women’s ability to raise capital compared to our male colleagues. That research is 100% accurate in my experience. We have to have 3x more traction, mitigated any risk, proven the competitive difference and not be perceived as a bitch. It’s a sad reality and I can’t wait to get to the other side of the table and invest in female founders one day.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

Investors, grants, and any other financial support specifically dedicated for female founders. And ensure those who award that money have had bias training or systems in place to mitigate inherent discrimination- we all are biased.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

You can’t be what you can’t see. If we don’t role model being a female founder for future generations, we won’t change the pattern matching. In addition, we know through research that more diverse teams (diverse gender, background, experience) produce better results. If entrepreneurs aren’t comprised of that level of diversity, the evolution in society will be stifled.

What are the “myths” that you would like to dispel about being a founder. Can you explain what you mean?

It takes 5x longer than you think to get something started. If you’re in this to have the big exit and make millions, you’re going to be disappointed. That motivation won’t weather the entrepreneurial storms and is the minority. Your ‘why’ has to be baked in your bones.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

Tenacity. You have to be willing to keep getting up again and again. In addition, you must thrive in the ambiguity and ‘build the plane as we fly it.’ Being rejected is a daily reality and your skin must be thicker than you ever thought possible.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. This will be one of the hardest things you’ve ever done. Ex: I went through 7 years of IVF with my husband, that battle was a great testing ground for me to keep my eye on the goal, keep finding a new way and never giving up.
  2. You need a tribe around you. Ex: friends, family members that will be there to pick you up, cheer you on and help you stay centered on this ride.
  3. Have financial reserves. Ex: it took me 2 years of working on TiLT before I took 1 dollar in any sort of salary. I did a variety of side hustles to bootstrap and downsized my family’s finances to survive. That sucked!
  4. One day at a time is real. Ex: There are days as an entrepreneur that you get completely overwhelmed with the roller-coaster of a start-up. One day at a time is a true survival tactic.
  5. Don’t get too much advice. Ex: There have been many times where I let my ‘imposter syndrome’ vice get too loud and drive me to seek too much advice. You have to trust your gut, experience and intuition.

How have you used your success to make the world a better place?

Every time we hear someone going through TiLT share the impact it had on their lives, that makes the world a little bit better. We have put our stake in the ground to revolutionize leave and that happens one day, one leave, one employer at a time.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

To create a new world of work in which work/ life integration is really a thing (not just rhetoric). People are celebrated for finding a balance, taking the time they need and not bragging for overwork.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Yes, Alexis Ohanian! We want to work with him on his mission for paternity leave, parenting at work and gender equality.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


This series was inspired by Female Founders First, a program by Barclays and Techstars designed to provide female founders with resources to grow, scale and advance their businesses.

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