How To Find Your Perfect Match With Mandy Ginsberg, Board Director At ThredUP And Uber, And Former CEO Of Match.com

I recently had the opportunity to speak with Mandy Ginsberg, member of the board of directors of Uber and, as of last month, thredUP. Mandy and I discussed her passion for leveraging technology to disrupt and improve our lives.

Prior to joining Uber’s board of directors, Mandy served as the CEO of the Match Group, which runs many popular dating apps including Match.com, Tinder, Plenty of Fish, Hinge, and OKCupid. Mandy shared how her experience as a CEO and her participation in a network of women leaders helped her succeed as a board director for multinational companies like Uber and thredUP. 

Nancy: The CEO of thredUP praised you for having “a track record of shaking up established industries with technology to create sweeping behavioral change.” When you start at every company you lead, how do you make sure the company is using technology to the fullest? And is the process more similar or different at every company?

Mandy: First off, I love it that you assumed the CEO of ThredUP was a woman. In fact, the CEO happens to be a man. One of the first reasons I decided to join the thredUP board was because I got a phone call from the chairwoman of the organization. She and I used to serve on a board together. Listening to her talk about the company, its mission, and its value proposition, made me excited to be part of a fast-growing disruptive organization. 

When I think about processes and disruption, I think about when I first joined Match.com in 2006. Match was looking for a general manager to start a second brand and run it like a start-up within the company. What drew me to the category (consumer tech) was that it was so full of disruption. Whereas, today, roughly 50% of marriages and relationships come from dating apps, back when I started in 2006, it was around 2%. If you believe it, people were embarrassed to tell you that they had met each other online. It wasn’t until I would tell them that I worked at Match.com that they opened up to me and told me that they had met online. 

Therefore, the disruption wasn’t just happening on the technology side, but the difference between 2% and 50% over the past 15-year span, has also done much to change the stigma and how overall society views online dating. So in a similar way, with thredUP, we’re also seeing a shift in the way buyers view thrift stores. Buying second-hand used to be something that people were embarrassed about, but with companies like thredUP, it’s not the case anymore. There’s a really interesting trend where technology is disrupting how we think about value and societal norms.

Nancy: How does your work as a board member differ from your work as a CEO? 

Mandy: Admittedly, being on a board is sometimes hard for a CEO, because you’re used to having your fingers in everything, and I am used to being a hands-on operator. So even though as a board director, you’ve got to really understand the business, you can’t get your fingers all in it because that’s really not your job.

If you’ve got a good board as the CEO, they can bring so much incredible perspective,  knowledge, and experience. It’s our job as board members to make sure the CEO or the management team is focused on the future vision. Board members need to be provocative and be a thought partner to their management team and CEO. The CEO has to execute, but their chances of future success are greater if they can evolve their course or learn from their board’s collective experience.

I get the best of both worlds, because I love being recognized for my unique operating experience and the CEO is thrilled because they’re being challenged to think about things in a new way. 

Nancy: When serving on a board, do you occasionally catch yourself and make sure you don’t act too much like a CEO?

Mandy: Yes. It happened when I was working for Match. We started acquiring more companies and also incubating others, like Tinder or Hinge. It became like running a portfolio of companies. All the CEOs reported into me, and at some point, I had to stop being a CEO. I was effectively the CEO of CEOs, and managing a portfolio gave me my first taste of board leadership (even though I was still the CEO for the portfolio). 

If you’re used to being the product person, going in there and drawing mocks and thinking about user experience, it can be hard to extract yourself. But that’s where, if the CEOs are open to taking advice from their board, they stand to gain all the knowledge that the board has learned as operators going up through the ranks and running a particular brand or business. 

Nancy: You’ve spoken about strong family influences, such as having a strong mother and entrepreneurial father and grandfather. What about your influences in the work world? 

Mandy: My grandfather immigrated from a small city right outside of Warsaw. When he came to the US, he and my grandmother had to start over from scratch. Because he had owned businesses back in Eastern Europe, my grandfather got so mad at me when I got my first paycheck. He said, “I believe you’re always going to do better working for yourself than for someone else.” 

That mentality is so different from many of my friends, who prefer stability and security. The fact that my family really emphasized grit and creativity, and with it a lot of hustle, that certainly influenced me and encouraged me to take the risks that I did in my career.  

Nancy: Have you had any mentors, groups, or organizations you’ve been a part of that supported your professional accomplishments over time?

Mandy: My generation didn’t have a ton of female role models and mentors, so I pretty much had to find my own way up the career ladder. In more recent years, mentorship has become more mainstream for women. So I’ve asked all sorts of people to be my mentor. I’ve always been a believer that if you really want to learn or understand just open up your mouth and ask. You’ll be surprised that many people are willing to mentor you, especially if you’re smart about how you leverage their time. 

It’s not enough to just have women in the workforce but you want to have people who really believe in them. In an ideal world, your company will set up the mentoring programs for you, but it can be difficult if you’re an introvert or you don’t feel comfortable sharing sensitive things with your assigned mentor. It’s not just about the work but also the work environment. 

It’s really important to connect the dots to people who might be in businesses that are adjacent to yours. Over the course of my career, I’ve connected many people in similar roles to one another, for peer to peer mentoring. For example, I’m part of a CEO group where we share a lot of things and we coach each other. From my peer CEOs, I’ve learned how to think about my next chapter after Match. In fact, one of the people who I’ve asked for advice is the chairwoman of thredUP. She’s one of the earliest female venture capitalists on the west coast and she’s got so much perspective. I sought out her advice and that’s ultimately how I ended up on the thredUP board.

Nancy: Non-profit organizations like Advancing Women in Product (now Advancing Women in Technology) support a number of women — and people of all backgrounds — who want to accelerate their careers. However, this can be difficult at certain inflection points, where they feel that their career starts detracting at their overall well-being. What techniques do you use to achieve work-life harmony?

Mandy: I’m amused that you used ‘work life harmony’ instead of ‘work life balance’. I do feel that between being a female, mom, and an executive some ball is going to drop. Just hope it’s not too big of a ball. Or drop on someone’s foot.

Jokes aside, it’s hard for women. We’ve got our careers but we also want to make sure our kids are taken care of, and for some of us who have husbands or partners, we also need to make sure that they’re taken care of as well. What ends up happening is that we don’t take care of ourselves. We end up neglecting ourselves and our health, or our mental space. My recommendation: even if it’s 5 minutes a day or an hour a day, do something for yourself. Get food for the soul like laughing with a girlfriend. Or go on a walk with yourself. Little things like this will keep you sane over time and help you keep your mental state sharp while juggling many things. 

With male executives, it’s a bit more binary. They go to work. They don’t think about all the other things that we as women think about. Like are our parents okay and safe? Are our kids getting sick with COVID? It’s a blessing and a curse. Women are more likely to be web thinkers. We tend to think about a lot of things at one time. That’s why I believe women make really good leaders. 

The interview has been edited and condensed.