Growing a Bank, Inside and Out

By Diane McLaughlin | Banker & Tradesman Staff | June 12, 2022

Pamela O’Leary
Executive Vice President and Chief Operating Officer, South Shore Bank
Age: 59
Industry experience: 37 years

Pamela O’Leary sees her embrace of lifelong learning as key to her career in banking, where she has worked mostly in technology and operations. But she did not even expect to have a career in the industry. She had been working in software development after college when an aunt suggested she look into a job at a bank. O’Leary then spent 19 years at Rockland Trust, where she said at one point she was one of just a few female senior vice presidents. For the past 18 years, O’Leary has been at Weymouth-based South Shore Bank, where she is the chief operating officer and interim chief technology officer. O’Leary has also been on several boards during her career and is currently board chair of South Shore Health, continuing a long tradition of South Shore Bank representatives serving on that board.

Q: What does your role involve?
A: I’m fortunate to work with an incredible team. One of my main roles is really to provide leadership for the team, to give guidance, and hopefully, to provide vision and strategy for the bank, not only from the business aspect, but also how do I help people to be effective and passionate about what they do. I love this place, and I think it’s important that we make sure that everybody understands really who we are, what our brand is, and what our mission and our values are. Our most valuable asset is our people that work here, and so we have to help educate them as we move forward.

We’re having fun along the way, too, because you’ve got to have fun in what you do.

I also make sure that we have good, strong operational control and direction so that we’re scalable, and that we’re secure. We have to continue to grow and evolve within our ecosystem that we have here, and that we’re doing the right thing – that’s actually one of our core values – by our clients, our communities and our employees. We strive to do that every day that we come in here. And we’re having fun too along the way, because you’ve got to have fun in what you do. 

Q: What are some challenges that you face in bank operations?
A: I look at challenges as opportunities, too. We have to stay ahead for our clients, and part of that relates to what’s happening with the evolving world and technology – making sure that we offer the tools and the services that larger institutions offer and how do we do that. It’s not only technology, but having the right talent to deliver it. We’ve onboarded a lot of great talent recently. We filled some new roles, like a chief data and robotics officer, and we brought in some great project management people. We brought in some front-facing people that are just amazing – we have to make sure that we’re looking for talent that meets our cultural needs too but also can meet the needs of our business clients and our consumer clients. 

We also try to grow internally with our people. We had 21 promotions just last year. We’re very proud of that. We make sure that we’re training our talent internally to move them up in the ranks, because it’s so important they can see growth internally and not just that we’re bringing external talent in. 

Q: What are you looking forward to that’s going on at the bank in the coming months?
A: We have a lot of great projects happening this year and into next year. We are upgrading all of our digital tools that are client-facing, especially for our business clients and for our consumer clients. No matter how they want to get in touch with us from a digital aspect, they’ll see a whole new experience and have more ways to interface with us. On the commercial side, we have a whole new system coming out. 

Also, from a brand perspective, we are really enhancing all our locations. So, when customers come in, they’ll have new ways to engage – whether it’s with our commercial lenders or our business bankers or our retail staff. We’re really making a better client journey for them coming in, and we’ll be able to enhance the experience for them, and we’ll also have some great learning aspects when they come in. 

The locations will be more of an educational center for customers when they come in and work with us. We’ve done a couple of updates already, but the plan is hopefully within the next year they’ll all be upgraded. A lot of it is going to really be tied to financial awareness and financial education and financial security. We really try to understand what the client wants and then try to meet them from that perspective – not our perspective – but really looking at what they want and listening to our clients.

Q: Have you found that you have to listen and respond in different ways than before?
A: Absolutely, with what happened with the pandemic, how technology has evolved, how people are evolving, and what they do and how they manage things. The pandemic made things happen faster from a banking perspective, and it made us have to pivot and to look at things differently. We had started that journey a while ago with interactive teller machines, and we have just continued that to let people bank the way they want.

Q: What are some roles or skills that you’re finding make a good fit for banking?
A: We’re in fintech. We need to make sure we’re partnering with the right technology. We have a chief strategy officer. A lot of larger banks may have that. At our size organization, those are positions that we see as important for us as we continue to grow. We have digital ambassadors, we have financial educators. So, our roles are changing, because it’s important that we change to be able to look at our needs, the needs of our clients and the needs of our community. There’s risk, there’s security, there’s technology, there’s data, there’s marketing, there’s all sorts of things you could do at a bank, and you can learn and grow from. Our interns come in, and they’re like, “Wow, we never thought about that.”

O’Leary’s Five Favorite Mindfulness Tips 
  1. Five-minute meditation
  2. Walking on the beach
  3. Deep breathing
  4. Yoga
  5. Audible
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