Kathleen Pierce-Gilmore - President & Chief Operating Officer, Raise (USA)

While in Las Vegas, attending the mammoth Money2020 global payments and fintech extravaganza, RFi Group’s Chloé James met with the impressive Kathleen Pierce-Gilmore, or ‘KPG’, as she is affectionally known.

Kathleen is a global expert in consumer lending, fintech, end-to-end P&L management, strategy development, talent management, people leadership and partnership creation. She is also a lot of fun! A former PayPal executive, she is currently leading the charge for one of the USA’s hottest fintech start-ups Raise and here are her thoughts on leadership, career fulfilment and living a truly joyful life…

How did you get where you are today and what, or who has been your greatest influence in business?

I have been extremely fortunate with the opportunities I have had through the years; from being able to take challenging classes in my younger years, to attending a great university with more than just great academics, to having the chance to take on important work in each of my jobs across the companies I have worked for.

If I think about the themes that have existed along the way that have enabled my progression they are curiosity, courage, and gratitude. If I think about how I have been able to find great roles, it mostly comes down to me expressing passion and excitement for something I care about or want to learn more about - like when I shared with a friend how much I loved American Express’s products and brand and she introduced me to a friend who worked in their internal consulting team, which is how I ended up joining the company.

"Learning to take on opportunities that have a high chance of not working out is difficult, but it often leads to the greatest breakthroughs and certainly the greatest sense of fulfilment."

I think about the times where I have discovered opportunities to do better for customers or for my company and have to find the courage to stand up for what I believe in and make the case for change, which has then led to greater leadership opportunities to drive the change. And most importantly, the times I have excelled the most and have had the most abundant personal growth and development is when I have felt deep gratitude. I have been so thankful and almost surprised by the people, the challenging problems, the learning I have had exposure to through the years, and when I revel in it, I find my energy and optimism and capacity to contribute and learn shoots through the roof.

What is the driving force behind your career goals/aspirations?

Starting out, I wanted financial security - plain and simple. I wanted stability. As I started to gain confidence and learn, I started to develop a passion for problem-solving and more curiosity for how companies work. My passion for financial health subconsciously drove my affinity for American Express and once I was in the financial services industry, I developed great passion on helping more and more people succeed financially through innovative and consumer-centric products and services. As time has gone on, I have sought ways to expand my reach on making that impact.

"My passion for
financial health subconsciously drove my affinity for American
Express and once I was in the financial services industry, I developed great passion on
helping more and more people succeed financially."

Have you ever made a business decision you’ve regretted and can you share it? And, what would you say is your greatest professional achievement to date?

have made many mistakes and continue to do so on pretty much a daily basis :)! I am not sure I have ever made a “business decision” that I have regretted because I believe everything is just data. You invest in something and it yields value - that is data. You invest in something and it doesn’t - that is data too. As long as you are constantly in learning mode, then you have nothing to regret. I have definitely impacted people in ways that I regret but have invested greatly from learning and growing from those experiences. I could say I also regret not seeing a few opportunities all the way through because I believe I missed out on some great learning in a few cases that I would value now.

My greatest professional achievement is more around the people I have built great relationships with through the years, my leaders, to my peers, to people I have hired and developed. I almost can’t believe how lucky I am to have worked with so many amazingly talented and passionate people in so many different opportunities and all they have done for me along the way.

"I believe everything is just data. You invest in something and it yields value - that is data. You invest in something and it doesn’t - that is data too."

What do you do to keep evolving your career, to ensure a fulfilling and successful longevity?

As hard as it is, I keep taking risks and they have been growing in magnitude through the years. I think I am like most people, and am afraid of failure in general. Learning to take on opportunities that have a high chance of not working out (for whatever reason) is difficult, but it often leads to the greatest breakthroughs and certainly the greatest sense of fulfilment. I have also really focused on making sure I am surrounded by people I trust and admire.

How do you achieve a balanced life and what activities do you participate in outside of your working life, that you see contributing to your business success?

I would be lying if I said I have balance! I have a rich life, but I am just like any other working mum - trying to keep it together at every moment. I have three kiddos who I adore and who hold a mirror up for me to see myself honestly. I also love running and it serves as therapy for me and also time for me to work through problems, practice difficult conversations, or plan my day. I think I am at my best when I feel good about how my kiddos are doing and when I feel physically healthy, so these are integral to my success in general.

Do you mentor others? And, what have you learnt in the process?

I do spend time investing in people. I am naturally curious about people and personally really enjoy deep connections with folks I admire and relate to. This has naturally led me to “mentor” folks but it never feels like that is what I am doing intentionally. It is usually more mutually sharing and listening and discussing and learning. I have learnt so much about what motivates people and what holds people back in being their best and constantly try to incorporate that into how I lead and how I manage my own experience.

What advice would you give to young women who want to succeed in the workplace and what do you see as the biggest challenge for future generations of business women?

"I think the biggest challenge for anyone now and in the future, is balancing the need to demonstrate competence and confidence while always remaining open to learning and taking risks."

Learn, take risks, learn, develop deep relationships with people you admire, learn, follow your curiosity and learn. I think the biggest challenge for anyone now and in the future, is balancing the need to demonstrate competence and confidence while always remaining open to learning and taking risks.

Women especially are often in a position of having to hold their own in a crowd of men (especially the more senior you get) and establishing a feeling of belonging and connection can be challenging when you are trying to prove you should even be in the room. I think this will continue to get better over time, but there will always be some need to be aware of it.

What’s the best piece of advice you have received as a woman in a leadership role that you would pass on to others hoping to get there?

"Don’t put your life
on hold for the sake of your career. I chose to have children relatively young compared to my peers and it was the greatest decision ever."

Don’t put your life on hold for the sake of your career. I chose to have children relatively young compared to my peers and it was the greatest decision ever. A female leader I admired invited me to spend time with her and her two young children while we were on an international assignment together and I saw how she navigated the chaos of it with grace and humour and it made me realise it would never be easy and I should just go for it. Knowing that I could have a life outside of work has made my work joyful and fulfilling and never a burden as a result.


To read the full WIL series and all past Australian Retail Banker editions, feel free to visit the archive centre on our website or follow @RFiMediaGRB on Twitter.

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