In ELLE.com’s monthly series Office Hours, we ask people in powerful positions to take us through their first jobs, worst jobs, and everything in between. This month we spoke with Gabrielle Rabinovitch, PayPal’s acting chief financial officer and SVP of investor relations and treasurer (say that five times fast!), who knows male-dominated spaces all too well after starting her career in investment banking. She recalls once working on an M&A assignment for a company that made industrial-sized boilers; when she asked to see them, she was directed outside, approximately 100 yards away, in the freezing cold—to an empty building. “It was a big ‘gotcha’ moment,” she confesses. Ever since, Rabinovitch has prided herself on being aligned with the values of the company she works for. “Caring about the mission and vision, caring about what they do, and caring about how they take care of their people is very important to me,” she says. That includes helping provide a service that allows people to buy what they want, when they want, and how they want, especially during the holiday season. Here’s how she got there.
My first job
My first teenage job was folding sweaters, but my first real corporate job was as an M&A analyst at Merrill Lynch. I worked on the mergers and acquisitions team for about two years, right out of college. Obviously, it was a very high-paced environment. Also, an environment where I was one of very few women; I think I was the only woman on my floor. Investment banking, management consulting—those types of areas are amazing training grounds to build executive presence, be given a ton of responsibility, and have an opportunity to be highly visible and gain a lot of on-the-job training. I thought it was a great way to start my career. I’m a big proponent of getting that diverse experience in your career and digging right in. What you get is what you give.
On being the only woman in the room
I felt like an outsider a lot of the time. I felt like I didn’t relate; I felt like I wasn’t included in the joke or the conversation. There were instances where I would be at a business dinner and a client would literally say, “I want to tell this joke, but I won’t tell it in mixed company.” Then I would get up and go to the bathroom, and I would come back and people would be laughing. Because I was the most junior person on the team, I would often go down and greet our guests and bring them up to a conference room and they would say, “Honey, can you get me a cup of coffee?” I had many of those experiences. One time, I corrected a senior banker when I was called upon to explain an analysis, and he said, “How do you know that? I’d think you’d be spending your time reading fashion magazines all day.” He said it in front of an entire group, and it really, really took me aback. It was an opportunity where I realized, this was not academia, this is not a meritocracy; you’re viewed in a certain way and there are certain preconceived ideas. It was eye-opening.
How I went from investment banking to PayPal
First, I went to Williams-Sonoma, and I got to the point where I wanted to take on more. I felt like I had stopped growing in my current role, and it was really an opportune time for me to move on. At the same time, PayPal had just become a separate public company, which was a very unique situation, to birth a company with a $41 billion market cap. It’s such an important leader within the digital payment space that, when I heard about the role, I was particularly excited, because it brought together my interest in technology, corporate formulation and business association and government, and it was also a much bigger platform for me to develop as a leader. So, I applied for the job, and I was definitely not at the top of the list—the recruiter made that pretty clear. I called him every week to let him know I was interested. Then I got to the point where I had another offer from a very prominent company, so I took the risk of letting the recruiter know, and very shortly thereafter I was meeting with PayPal’s former CFO. I prepped so much for that interview, because I knew it was my one opportunity. There was nothing that I wasn’t prepared to answer. I put so much pressure on myself, and fortunately, I was able to impress the team.
Best career advice I’ve ever received
Taking calculated risks, and that is really consistent with what my transition to PayPal was.
Why PayPal’s mission is critical
The whole idea of democratizing access is so incredible: how expensive it is to be poor, and the fact that PayPal sits between merchants and consumers to make transactions easier, safer, and more secure. This whole idea about how we facilitate and enable both person-to-person payments and consumer payments was incredibly exciting to me. And also [being] right at the nascency of just becoming a public company with an incredibly rich history behind it: founded in 1998, acquired by eBay in 2002, and this whole story which then developed into corporate activism and separation.
What I love about working in tech
PayPal really is a meritocracy; it is truly a place where lots of people thrive. What I find different about working at PayPal versus other jobs I’ve had is the consistency of such capable, excellent, smart people. It’s very fast-paced, so, initially, I felt like my head was spinning. It was a real learning curve with digital payments. I gave myself 90 days to know everything, because you can only ask so many questions before you lose credibility. There’s a very “come as you are” attitude. I’ll show up dressed up, and other people will show up in T-shirts and flip-flops; no one is judging people based on how they look. They want people who are thoughtful and engaged and passionate about the business.
How I psyched myself up to be CFO
By reminding myself that nobody would be asking me to do this if they didn’t think I could. I’m sure I seemed a little shaky at moments in time when I was finding my footing, but each successive week felt more natural, and it felt like I started to develop a good rhythm, not without challenges, but it started to take shape. To me, it’s about serving our people. Somebody needs to be in this role, and it requires a ton of energy, so I really wanted to be in service to our teams as we were moving through this transitional time. This year, as with many companies, has been one of intense change. So I needed to step up and give back.
The proudest moment of my career
Without a doubt, being acting CFO. One of my main influences for my interest in business was my mother. She had a career and then took a step back to have kids and stay at home, and she always regretted not returning to work. She passed away in 2005. I always think, “This would’ve been the moment where she’d be so proud.” I’m a people pleaser by nature.
This interview has been edited and condensed.
Deputy Editor
Claire Stern is the Deputy Editor of ELLE.com. Previously, she served as Editor at Bergdorf Goodman. Her interests include fashion, food, travel, music, Peloton, and The Hills—not necessarily in that order. She used to have a Harriet the Spy notebook and isn’t ashamed to admit it.