Career Journeys to the C-Suite – PayPal’s Peggy Alford, Archie Deskus and Gabrielle Rabinovitch

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Pictured from left to right: Peggy Alford, Archie Deskus, and Gabrielle Rabinovitch.


As a part of PayPal’s Women’s History Month celebration, we sat down with the three leaders who serve on PayPal’s Leadership Team – Peggy Alford, EVP of Global Sales and Merchant Services; Archie Deskus, EVP and Chief Information Officer; and Gabrielle Rabinovitch, SVP and acting Chief Financial Officer – to learn about their career journeys, the experiences and challenges that they encountered and learned from, and the advice that most helped them in their careers. We hope their insights and advice help everyone seeking to advance their career. The answers below have been edited for length.

Looking back on your career, what experiences or learnings do you think most helped you excel?

Peggy: I've focused my career on this idea of continuous learning – always trying to broaden and deepen my understanding of business by getting lots of different types of experiences to bring together and drive growth within a company. If you look at my background, it looks more like a lattice than a ladder. I have found that a strong financial background is valuable regardless of where one eventually works in a company. Truly understanding the drivers of growth, metrics for success, and financials is a great basis to have.

From there I went into general management-type roles, working very closely with customers in a sales function and with our employees, which was helpful. I co-ran human resources for a while, which helped me understand how employees drive customer experiences and growth. So, for me, it's been about getting perse experiences that you bring together to understand how to grow a company, and how to serve customers in a scaled way.

Archie: The best experiences were probably the ones where I perceived, or the company perceived, the greatest risk. Ones where there hadn't been success before, because it forces you to operate and think differently. I had one role where I was asked to lead the largest SAP software implementation in aerospace at the time. We'd failed three times in the process, and I learned so much from that. 

Gabrielle: The experiences that helped me develop skills to be able to pivot rapidly, and play a different role in different contexts, started with some of my academic work when I pursued a law degree and an MBA at the same time. That required the ability to be both resilient as well as agile. From there, I pivoted from that perse academic experience into an environment where I was in investment banking and I served as a generalist, predominantly focusing on the industrials space, but I was also forced to get smart quickly in a lot of different areas. Some of these very demanding experiences helped develop the skills that have allowed me to take on this opportunity and serve PayPal in a way that has allowed me to advance.

When you faced big challenges in your career, what are some successful strategies you employed to overcome them?

Peggy: What I've realized is creating the best team and then enabling that team to be successful by making sure everyone understands jointly what we're trying to get done, and giving credit for what each person brings to the table, is important – because everyone wants to feel like their specific contribution is being recognized. 

An example of this is when I had the opportunity to be the CFO of Before that, I had only worked on the accounting and controllership side of finance. Suddenly when I became CFO, my role became much broader. What enabled me to be successful as CFO was walking in with the mindset of wanting to learn from the people that were there and admitting what I knew and didn't know. Also, being confident in the fact that I did bring something to the table, despite not having subject matter expertise in all the areas I was being tasked to lead. With this kind attitude, I realized you can get people who want to help bring you along and help you learn, and you're also then able to give them the opportunities to shine, which is what everyone wants to do in their career.

Archie: Three strategies come to mind. One, when you have complex problems or challenges that you think you can't attack, focusing on what matters the most in terms of the results has always helped me to get the prioritization and the alignment of people. 

The second is asking for help or seeking help when you need it. Too often we think that it's a sign of weakness, especially when it comes to our peers or team. It's easier to ask your boss for help when you need it. We need to look at asking for help as a sign of strength and not as a sign of weakness. 

Then the third one is keeping perspective, which is one of the biggest challenges of my career. A lot of times you think about that end state, but you have to remember that it's a journey and about setting milestones along the way. So, every six or nine months, meeting a milestone or victory is important for your mental state and feeling like you're making progress. The same goes for the rest of your team. 

Gabrielle: Stepping first into being interim CFO, and then acting CFO, has been a major challenge – it totally changed my role in the organization, and what was expected of me both internally and externally. It's natural in a situation like this to have self-doubt and to wonder whether you have what it takes to be successful. 

What helped me through this is grounding myself in what my purpose is and why I'm here at PayPal, which is to serve our organization. It's a privilege and an amazing opportunity to be asked to lead our finance organization. I've centered myself on why I'm here, and that is to give back and support our team – both the finance team and our broader organization. That has helped me focus on how I need to operate and what I need to prioritize.

What advice would you give to women who aspire to leadership roles in your field?

Peggy: This applies to men and women – take a shot at it! One of the most difficult things to do is to tell yourself you're ready and you should go for it, when maybe you could name three or four things that make you not ready. You need to recognize that most people that get a new position, a new job, or a promotion, don't hit all the boxes for readiness. You're going to be most familiar with what your shortcomings are, but don't let that stop you from giving it a shot.

The other thing is – and this can be more specific for women who are often more critical of their own shortcomings and kind of want to feel like they're completely ready before they go for something – don't be that person that is always second-guessing yourself and then never giving yourself a shot to just go for it.

Archie: Don't give up. I see too many women in tech especially when they get to mid-career bow out. We need more women to make it past that mid-career. There's so much more flexibility today than my generation had in terms of taking time off when you need it, when you have kids, or just asking for more flexibility. Break it down and figure out how not to make it so hard and not to put so much pressure on yourself. 

The other advice I would give is to speak up. There's a lot that needs to change in tech to change the culture. Without speaking up, you can't change the world. And you don't have to do it in a negative way. There are a lot of constructive ways to raise the challenges that you face, whether it's through employee resource groups or your immediate leadership. Most companies have some type of support structure that you can tap into to bring up those kinds of concerns. 

And then the last advice that I would give to women is, we try to do too much. This is the advice I give to my kids: if you want a career and you want a family, don't feel like you have to do it all. But that's the pressure we put on ourselves to be perfect in all aspects of our lives. Balance where you're going to make the highest impact, both on the family side and on the work side. With everything else, look for help.

Gabrielle: Taking calculated risks is a big one. Think big and play off your strengths. Knowing what your strengths are, and playing to them by putting yourself in positions where those strengths can be amplified is critical. 

In finance, subject matter expertise is an important platform for growth when you're advancing. This is true in other disciplines as well. The best way to distinguish yourself early on is to be a subject matter expert and demonstrate excellence. Showing that you have the skills to master one area can often give leadership teams confidence that you are ready to advance and take on new areas of focus and responsibility. Take risks, ask for more, and be sure that when it comes down to the area that you are focused on, truly become an expert, and look for opportunities to demonstrate that.

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