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Jessica Eggert, CEO And Cofounder Of LegUp


This Trailblazers series takes a look at the pivotal milestones that make up the life trails of inspiring women from a diverse array of backgrounds and experiences. We all know what social media profiles display about the end results women have achieved. This series is intended to take a deeper, more authentic look at the journeys they have taken to get there. 

Jessica Eggert is the CEO and co-founder of LegUp, a company that is making child care more accessible for working parents. As a working mother of two herself, as well as a startup advisor and community builder, she has a passion for supporting women and people of color across their personal and professional lives. 

After learning more about the trail that Jessica has blazed, I got the chance to ask her some questions.

Rebekah Bastian: Your professional path has taken interesting turns, from operations to DEI to entrepreneurship. How have you approached growing in new areas and making career pivots? 

Jessica Eggert: I’ve approached my career by finding subjects that are interesting to me, with complex problems that needed change at the root level, and ones that affect entire systems. Maybe I’m a glutton for punishment? I’ve never been bound to a specific industry; I just know I want to create fundamental, positive change in the world, build a legacy, and make sure my children have a clear path to opportunity. Plus, I’ve always let myself be just naive enough to unapologetically walk into a room and think that I can be a catalyst for change.

I started with business operations because, at the time, it was an area preventing this billion-dollar business I worked for from growing efficiently. I moved into DEI because it was affecting people who looked like me from gaining wealth and power, and I could apply my skills gained from working in operations. And then I got tired of working hard to create fundamental change, only to get pushback from people who weren’t willing to do the hard work themselves. So I started building companies.

Bastian: You’ve used your platform to advocate for Black women in a time when many feminist-branded spaces and businesses have been outed for their poor and even abusive treatment of women of color. Why continue to speak up and share your perspective despite the personal risks?

Eggert: When companies, brands, and venture funds talk about supporting diverse people, most focus their sights on supporting women. Women in tech, women entrepreneurs, women fund managers. But I think that’s a cop-out. Because most of these organizations still focus on white women only. Now, I can’t boil the ocean and speak for every person who identifies as a woman, but I can speak up for myself as a black woman and ask these leaders to look beyond their comfort zone and be aware of and support the intersectionalities of women.

Bastian: You mentioned experiencing burnout a few years ago. What factors led to that, and what steps did you take to recover? 

Eggert: I experienced burnout after putting everything I had into a company that didn’t value me or people who looked like me, and didn’t care to build a diverse community when doing so would have only made the company stronger financially. I wanted this company to go the distance and so I kept pushing against a wall that was never going to budge. And when I left, I didn’t realize just how draining that experience was. Feeling such professional challenges while missing out on parts of my child’s life was not in line with my values and it didn’t justify the personal sacrifices that I was making as a working mom.  

I know so many parents can relate. One thing that moved me forward during this tough time was writing; I wrote about my experiences, the people and spaces that moved me, and I started planning my next career move. I envisioned myself as a powerful woman who changed the world, let go of people and experiences that tried to bring her down, and who said yes to every opportunity that was in front of her. 

I also envisioned building a company where I would create space for all types of families, to ensure my experience didn’t have to be everyone’s reality.

Bastian: Tell me about what led you to starting LegUp. 

Eggert: One of those opportunities that was in front of me at the time was the opportunity to have a second child. My husband and I were in a place financially where we could afford to raise another one the way we wanted to, and biologically, the timing was right. So we said “yes” to another baby, and then crazily (and lucky!) enough, we were pregnant within weeks. 

 But in all that excitement, we had forgotten to get on waitlists while we were trying. I knew we were already behind, so I started the long arduous process of finding quality programs, joining all the waitlists, sending the checks. I couldn’t believe that in a time when we have self-driving cars, I should have to write checks to join child care waitlists, and then never receive updates and just hope they’re going to offer me a spot in time for me to get back to work. 

After doing some research and chatting with dozens of child care programs, I realized that the industry was run by small business owners, primarily women and people of color, who don’t have the support they need to care for our children every day and run an operationally efficient business….and they’re barely making minimum wage. 

So I figured out how I could create fundamental change for the industry, give more women and people of color a path to profitability, help other parents never have to go through the stress and fear that I’ve experienced twice now, and clear a path to opportunity for my children in the future. Starting LegUp was the obvious next step for me.  

Bastian: A recent report revealed that “Many Americans pay more for child care than they do for their mortgages, even though the wages for those who provide the care are among the lowest in the United States.” How do you see these imbalances being resolved? 

Eggert: This is difficult—what many don’t see are the costs associated with running a quality program. 

In child care it’s hard to have economies of scale because it’s a service-based business with skilled labor, and programs need low staff-to-child ratios which can’t be replaced with technology solutions. So in order to make this a more sustainable business model long-term, we have to look at pulling on other levers within the business to create significant change. This is exactly where LegUp is making an impact.



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