The M Dash

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PayPal’s Jill Rose on Seeking Out Feedback and Handling Workplace Politics

August 03, 2018 | Filed in: Woman of the Week

Jill Rose, a senior director and general manager at Paypal, is a rare bird: There are few women at her level in the tech industry, and she’s the first to admit that it’s a bit of a boys’ club. But if anyone has the grit to break into the upper echelons, it’s Jill—she rose through the ranks at multiple companies, earned her MBA while working full time, and has surrounded herself with a rock-solid network of advisors. Here, she gives advice on building close relationships with higher-ups, seeking out feedback, and handling criticism even when you don’t agree with it.

Paypal Jill Rose

Jill wears the Noel dress, the Single Bezel necklace, and the Pave earrings.

I’M A TRIPLET, and also have a sister who’s 16 months older, so I grew up as one of four siblings very close in age. It was a competitive environment—it made me innately pragmatic, and very ambitious, and I think that influenced my career.

AFTER I GRADUATED FROM COLLEGE, I knew I wanted to get my MBA, but I didn’t want to pay for it, because my undergraduate education had already cost so much. So I got a job at a company that had an incredible tuition assistance program—they would pay for me to get my MBA, and I didn’t have to commit to staying for any period of time beyond that. I thought, I will clean toilets if you pay for this. I’ll do anything! My first job there was in collections. My parents said, “What are you doing? We just paid for this great education, and now you’re working in collections?” But that was the job they had available when I walked in.

Paypal Jill Rose

Jill wears the Lydia dress in boucle and the Pave earrings.

IT TOOK ME ABOUT THREE AND A HALF YEARS to finish my MBA, but I got it done. I worked 40 hours a week and went to school at night. Meanwhile, I worked my way up from collections and had a bunch of different jobs within that same company. The last job I had there was chief of staff. The key for me was keeping my eye on the long-term goal—getting my master’s degree—and not necessarily what I was doing day-to-day, even though that became very rewarding throughout my five years at the company.

JUST AS I FINISHED GRAD SCHOOL, my company was downsizing and offering generous severance packages. It was fantastic timing, because my husband was getting transferred to Baltimore, so I took the severance package and we moved. I worked some temp jobs, and then a recruiter found me and introduced me to a company called I4 Commerce. I interviewed on a Friday, and they offered me the job that Monday. I was in charge of sales operations, and I was the 45th employee they hired. It was probably the most exciting time in my career, because I was part of a small team that was trying to revolutionize online payments. I had never had so much fun at work. I did that for two years, and then we were acquired by eBay, which owned PayPal at the time—and that’s how I came to PayPal.

Paypal Jill Rose

Jill wears the Taylor dress in deep plum and the Pave earrings

I’VE HELD A NUMBER OF DIFFERENT TITLES at PayPal, including General Manager of PayPal Here, which is a mobile card reader. For the last two years, I’ve been the general manager of the medium business customer segment. I didn’t have a pre-determined plan for moving up within the company, but I was always ready to pivot when I got the chance to try something new. I advanced in part due to my advocates within the company, who looked out for me and said, “I think you can do this,” and then I put my hand up when opportunities arose.

CULTIVATING A DEEP BENCH OF ADVISORS, consisting of both current and past colleagues, has been critical for me in my career. One of them is someone I worked for when she was a VP at PayPal. She was a real powerhouse, and it’s pretty uncommon to see a woman at her level, especially within a tech company. She was a big inspiration. Now she’s retired and sailing around the world with her husband and two dogs—how awesome is that? We’re still in touch, and she continues to provide me with a lot of advice about navigating different situations within the company.

Paypal Jill Rose

Jill wears the Noel dress, the Single Bezel necklace, and the Pave earrings.

IT’S ALWAYS AWKWARD when someone comes to you and says, “Hey, can you be my mentor?” Of course you want to say, “Sure, I guess,” but it’s not the best way to kick off a close relationship. Personally, if I want to establish a relationship with someone, I ask that person for specific advice on solving a problem. This applies to people who are senior to you as well as your peers. I’ll also ask junior-level people for their feedback. Then, as the conversation develops, you learn more about that person and can lean on them going forward. I think you could call that mentorship, but it’s more of a two-way street in terms of getting advice and direct feedback. There are always people that you want to be closer to, professionally, but you never want to push it. It’s kind of like dating. You either click or you don’t.

I’VE LEARNED THAT IT’S CRITICAL TO BE SELF-AWARE and take time to think through how you interact with people, observe their actions towards you, and perhaps change your behavior as a result. To do that, you have to get 360-degree feedback on a regular basis. The more often you get feedback from your team members and peers, the more pressure it takes off of the feedback process. I use a particular tactic called “Start, Stop and Continue,” where I ask people “What would you like me to start, stop, and continue doing?” That’s much more helpful than going to someone and saying, “Tell me how you think I did last week.” You get very specific insight into what you need to change or what you need to keep doing. I definitely have received feedback that I disagreed with, in terms of how others perceived me. But it’s important to remember that people’s perceptions form their reality. Regardless of how I intend to be perceived, I still need to reconsider my behavior if it’s interpreted in a way that doesn’t fit with how I want to be seen. Taken all together, that constant feedback helps me to evolve.

Paypal Jill Rose

Jill wears the Lydia dress in boucle and the Pave earrings.

WHENEVER I’VE MOVED FROM ONE JOB TO ANOTHER, my instinct is to think, But I haven’t mastered what I was doing before! There’s still work to do there. And then there’s self-doubt about whether I can do the new job: Do I have what it takes? Am I smart enough? When there’s a confidence gap, it helps me to take time to reflect. I block out some time every month to pause and think through how I’ve performed as a leader, as a peer, as an employee, and just as myself. Based on that, I think about what I need to work on, and what I’m doing well. I also have a coach outside of the company, and I meet with her on a monthly basis. That has been game-changing. It’s like business therapy. I’m working on being a better partner and advisor, and offering input even when I’m not running something.

Paypal Jill Rose

Jill wears the Taylor dress in deep plum and the Pave earrings.

WHEN I’M STRESSED, I WORK OUT. I know that’s a no-brainer, but it helps me focus. Lately, I’ve gotten into Orange Theory. I also spend a lot of my free time with our five-month-old puppy, Riley. My husband is in the boat business, so on the weekends we’ll go boating in the Chesapeake Bay with the puppy, spending the night on the boat and exploring new towns during the day. It’s great to feel like you can go just about anywhere.

Photos by Jessica Todd Harper


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Charlotte Cowles is a New York-based writer​ ​and editor.​ ​Her work has been published in New York Magazine,​ Harper's Bazaar,​ and Art in America. She'd always rather be at book club. Read more of Charlotte's posts.


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