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Jennifer Henderson: Revolutionizing Work Place Leave

Jennifer Henderson: Revolutionizing Work Place Leave

Jennifer Henderson

Welcome back! Spiffy here, your interplanetary journalist reporting from Planet Earth with an eye on entrepreneurs making the world a more equitable place. I’m here today with Jennifer Henderson, founder and CEO of TiLT. 

Spiffy: Welcome Jennifer, I’m excited to hear about your endeavor! What can you tell me?

Jen: You can call me Jen, Spiffy! It’s great to be here. So, TiLT is revolutionizing leave management to help companies improve retention, streamline processes, reinforce a diverse culture, and ensure compliance of employment leave. Our leave experts — which are real people! — and our beautifully-designed software, ensure success at every stage of the leave journey. We're doing for employee-leave what TurboTax did for taxes!

Spiffy: Wow, Jen! That sounds like a major transformation. The U.S. — and many other countries — definitely require major improvements in employee leave. What motivated you to tackle this issue?

Jen: Well, Spiffy, I spent 15 years in corporate America working in operations, talent development and leadership. As a professional mom with two small children, I experienced career stagnation and pregnancy discrimination when I disclosed both of my pregnancies. The research shows that this maternal bias, and similar discrimination, originates during the leave of absence process. So I set off on my own and founded TiLT to revolutionize leave in the workplace. 

Spiffy: Way to ‘be the change’, Jen! So what is the mission at TiLT?

Jen: At TiLT, we are working to abolish the penalty of caregiving, the stigma of parental leave and antiquated employee leave processes to allow emerging generations to truly level the playing field for pay equality and equal representation in key leadership positions. Our company will turn rhetoric into results for organizations who aspire to do better for their employees.

Spiffy: How are you doing this? 

Jen: We have supported over 150 employee leaves through our TiLT process and retained 100% of those employees for their organizations after they return from leave. That statistic demonstrated the efficacy of our solution and the tremendous cost savings that organizations stand to gain by managing leave correctly.

Spiffy: That’s phenomenal, Jen. I mean, with this sort of success, did you ever encounter any failure, or times when you were ready to just give up?


Jennifer Hudson 2

TiLT- revolutionizing leave at work. (Photo courtesy of Jennifer Henderson)


Jen: You know what, Spiffy, we were turned down by 123 investors when we raised our first round of capital. That consistent flood of, ‘No, you're too early, it's not a problem worth solving, you're too niche....’ added fuel to our fire — not only to prove them wrong — but to come back some day on the other side of the table and invest in female founders in a more effective and fair way.

Spiffy: I’m not sure I would have kept going. That is what I call determination! What other kinds of lessons are you learning?

Jen: Well, Spiffy, I recently had a mentor share some valuable advice, explaining that there are three actions we can take for every problem we face at TiLT:  1) the right action, 2) the wrong action and 3) no action at all. It was a great reminder that not getting it right the first time is okay but not trying at all is the worst answer.

Spiffy: That is sound advice. I’m going to remember that! Before I take off, is there anything else you’d like to share with our audience?

Jen: You know, Spiffy, the 'new world of work' is forcing companies to accelerate work/life integration, diversity and inclusion initiatives and caregiver benefits and resources. People working from home during COVID-19 brought 'real-life' out of the back office and into the forefront — with kids, family members and pets — on Zoom call, after Zoom call. I’m proud to say that TiLT works everyday to amplify gender equity, bias reduction, and work-life initiatives to allow these new realities to be supported for generations to come.

Spiffy: I will wager a guess that you’re going to be crucial in shifting that balance. Thanks so much for talking with me today, Jen. It’s been an absolute pleasure!

Jennifer Henderson is the 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. (Nominated by Techstars)