Navigating big life moments at work: Jennifer Henderson (Founder & CEO, Tilt)

Listen to our recent episode with Jennifer Henderson, Founder & CEO at Tilt .

We talked about her disappointing experiences in corporate America that led her to building Tilt, the history of leave, the #1 way to create gender parity in the workforce, and what it looks like to successfully help people navigate these big life moments.

Read the highlights below. ??

1. Jennifer's disappointing experiences in corporate America that led to Tilt ??

Parallel to her 15-year career path in corporate America with Fortune 500 companies, Jennifer and her husband faced a seven-year challenge of in vitro fertilization in their quest to start a family.

She says that this uncontrollable aspect of her life pushed her to excel in areas she could influence, like her career progression.

She became the epitome of ambition, climbing the corporate ladder with promotions every two years.

However, everything changed when she became pregnant.

Suddenly, the recognition and opportunities she had earned vanished overnight, marking her first encounter with a glaring workplace injustice.

Despite this setback, the joy of expecting led her to overlook the issue initially.

But, history repeated itself five years later with her second pregnancy, culminating in a rescinded promotion.

This was her breaking point and the inherent wrongness of it all led her to start Tilt.

2. The #1 way to create gender parity in the workforce: equal utilization of leave ??

She believes the best way to get to gender parity at work is by making sure everyone uses their leave the same way.

She thinks it's time we ditch the idea that women are the primary caregivers.

If we don't, she's worried women will keep getting the short end of the stick when it comes to pay.

According to her, the best companies out there are breaking this mold by having their top folks fully use their leave time, showing everyone it's okay to do the same.

3. Why you should introduce more flexibility into your leave policies ??

Jennifer says that even with a solid leave policy in place, we must acknowledge our unique humanity.

For instance, while one person may wish to take their entire 12-week leave in one go, another might prefer to split it up or even return to work part-time for a while.

It boils down to acknowledging our differences.

She understands that some might think, "Sure, that sounds ideal, but it's just not practical at my company."

Nevertheless, she believes there's often too much rigidity.

She says you should ask yourself two questions:

1. What aspects of your policy can be personalized?
2. How can you introduce flexibility and customization into your leave policies?

A one-size-fits-all approach simply doesn't work for leave of absence.

Jennifer champions the idea that creating room for personalization is the gold standard.

4. How AI is impacting the leave management space

AI plays a pivotal role in the world of leave management, and its impact continues to expand.

Jennifer shared an insightful example from Tilt, where they've developed an AI-powered system capable of processing various leave laws.

This system is self-improving, becoming more efficient with every case it processes. It's designed to continually enhance its capabilities, which allows for the automated assessment of eligibility and determination of the necessary steps for a successful leave, all tailored specifically to an individual's needs.

This personalized approach is crucial, as every leave scenario is unique.

Addressing sensitive topics—such as the emotional challenges of in vitro fertilization or pregnancy loss, which are often subjects shrouded in silence—is another area where platforms like theirs can truly make a difference.

Jennifer believes that we are only beginning to tap into the potential of AI in this field.

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Jennifer's definition of a Modern People Leader ??

"I often remind my team that being a people leader or a manager is a privilege and an honor. Approaching this role without recognizing its significance means you're already at a disadvantage.

This brings me to another point: the effectiveness of coaching over authoritarian approaches. I'm an advocate for servant leadership and, more recently, conscious leadership, believing in the power of fostering partnerships, illuminating the contributions of others, and ensuring they have a voice at the table. These principles, I find, are what distinguish exceptional people leaders.

Lastly, managing a fully remote, distributed team—a challenge we embraced even before it became a widespread necessity—has been an incredibly humbling journey for me. The demand for clear and effective communication has never been more critical in my career. I'm continually reassessing how we communicate: what we say, how we say it, ensuring our messages are understood, and verifying that the impact aligns with our intentions."

The career advice Jennifer would give to her 22-year-old self ??

"Enjoy the ride. As a quintessential overachiever, always striving for the top, I realized I missed appreciating the milestones and even the challenges along the way. This realization hit hard early in my career when, after 'making it,' I found myself profoundly unhappy. It led to nearly losing my marriage and a state of poor health. It was a tough lesson, but it forced me to reassess my priorities and learn to value the journey more than the destination."

Go listen to the full episode: Apple | Spotify

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