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Kevin Barry, President of Fidelity Workplace Investments

Moving up the ranks in any industry also means earning new responsibilities and learning new skills. Leading a large organization is one of those. Today’s guest is Kevin Barry, President of Workplace Investing at Fidelity Investments. He joins host J.R. Lowry to share his career journey from majoring in Government to having executive roles in the field of finance. Kevin discusses the importance of having management systems and why they should be tailored depending on the kind of team you’re leading. The two also discuss the effects of the pandemic on organizations, discussing topics such as remote work, work-life balance, and how companies can stay competitive to attract talent. Plus, Kevin shares insights on how saving behavior has changed through the pandemic, the recent financial market declines, and in the face of rising inflation, and shares financial wisdom for our audience. Don’t miss out on this jam-packed episode.

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Kevin Barry, President of Fidelity Workplace Investments

On Leading a Large Organization and On His Career Journey Through The CIA, Pepsi, Gillette, and Fidelity

In this episode, my guest is Kevin Barry, whom I first met when we worked together at Fidelity Investments starting back in 2006. Kevin is now President of Workplace Investing at Fidelity, a role he has held for the past 5 1/2 years. If Fidelity administers your 401(k), 403(b), stock plan, pension or medical benefits, all of that falls under Kevin’s remit. He joined Fidelity 16 years ago and came up through the finance function before becoming Head of Stock Plan Services and then moving into his current role a few years ago.

Prior to joining Fidelity, Kevin was in the finance function at Gillette. Prior to that, he was in the finance function of  Pepsi’s Frito-Lay division. He started his career as an Analyst for the Central Intelligence Agency. He’s a Trustee of the Boston Ballet and a Seven Generations Board Member for CityYear. He earned his Bachelor’s degree in Government from Harvard University and his MBA from Dartmouth’s Tuck School. He and his wife Patti live in the Boston area and are the parents of four adult children.

Kevin, welcome! Thank you for doing the show. I appreciate it.

Thank you.

You have a big job running the Workplace Investments Unit at Fidelity. Give the audience a sense of its scale in terms of how many companies you support, how many individual plan participants you support, employees, assets, all of that.

I’ll give you a couple of numbers. It’s tough to have just one encapsulate all of it. We provide a range of benefit plan services that we provide to companies and their employees. It’s, depending on how you count, either in the range of 22,000 to 24,000 corporate entities and tax-exempt institutions. About 37 million plan participants [employees] are in those programs. Assets that we administer depend on the market but have been in the range of $3 to 3.2 trillion, and [we have] a little bit over 10,000 employees that take care of those customers every day across the whole range of benefits we service.

Those are some big numbers. I, for the first time in many years, don’t have a Fidelity administered 401(k). I’m working over here [in London] and under a UK pension scheme at the moment. It’s a whole other world to figure out relative to the way things work in the US.

You were in the consumer products industry before you came over to Fidelity. What was it that led you to first join the company when you did so back in 2006?

It was not some big planned career move or even a deep passion for the industry, believe it or not. I was working for a company here in Boston, Gillette, which was sold to Procter & Gamble. We had decided we put down roots in Boston, that we wanted to stay here and for me to make a career as best I could. P&G bought Gillette. P&G is a terrific company but all roads lead to Cincinnati.

It's always helpful to have a core skill set. You can always fall back on that. Click To Tweet

When Fidelity approached me during the merger, I’d had a good experience with Fidelity as a customer and decided to take a calculated leap of faith that I could figure out a way to add value in the world of pensions and 401(k)s, even though I knew very little about it. It let me keep my family where they needed to be. It was an exciting new adventure to jump into.

You and I joined there right around the same time. I was coming out of McKinsey at the time. For me, it was a fairly big change as well. I hadn’t done much financial services work at that point. Here we are, a numer of years later. You’re still at Fidelity, and I’m still in financial services. Clearly, the move worked out for both of us.

You were a finance guy. You came up through the finance function. You became the CFO of the Workplace Investing unit before you took on that Stock Plan Services role. How do you feel coming up through the finance function prepared you for that ultimate shift into general management?

I’ve thought about that. It’s always helpful to have some core skillset that’s a key piece of your responsibility that you can always fall back on, that you know intuitively, and where you have a high degree of competence, because you are going to get stretched in many other ways. Having a diverse finance career before moving into general management gave me a fundamental understanding of the financial management of an enterprise, cost management, revenue generation, and assets and liabilities.

I’m not an accountant or a CPA but have the fundamentals of accounting and balance sheet management. If you have a broad career in finance, it gives you a sense of the workings of the entire enterprise, at least through a financial lens. It’s not unique to any one function. You see how all the different parts of an enterprise work together either to create value for customers or to support the enterprise from more of an infrastructure standpoint, and how it operates in different economic conditions. It gives you a broad toolkit from a specific lens. It’s something that I fall back on regularly. I probably spend less time than some of my peers going into the details of the financials just because I have some muscle memory that I rely on pretty frequently. That works for me.

I’ve had a lot of people who I’ve worked with or who have worked for me who haven’t had that finance background. It’s tough in some ways if you don’t have a stint in finance to develop that deep understanding you need if you ultimately want to move up in an organization because it’s so foundational. It seems to be lacking for a lot of people. It’s a good way, I’ve always thought, to come up.

It’s one of those things where it’s important to know what you’re looking at, what it means, and what it doesn’t mean. You can be misled sometimes by financial data if you don’t know the right questions to ask, and it can lead you to bad decisions if you are not careful.

When you moved into that Stock Plan Services role, you had a broader range of functional accountability, more of a general management set of activities that you were performing. What did you find that you had to work hardest at learning coming out of the finance function?

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Kevin Barry on financial management: It’s important to know what you are looking at, what it means, and what it doesn’t mean. You can be misled sometimes by financial data if you don’t know the right questions to ask, and it can lead you to bad decisions if you’re not careful.

There are a couple of things I knew intellectually going in, but it took me a while to internalize them. One is customer-facing. Coming from a career of being in support roles, I had been in a few meetings with customers, but to be in the front of the house, representing the brand and the business role, where you are making commitments and backstopping the services and making promises on a regular basis, then being accountable to follow through on that, is a different skillset. How do you communicate with customers? How do you communicate and inspire a large frontline workforce that can be lots of hourly employees doing roles that you would never see in a finance function?

The other part of it is direct accountability. For better or worse, you eat your own cooking every day. The decisions you make come back to either reward or bite you, depending on how it turns out. There’s no hiding from it. Whereas in finance, you give the best advice you can and try to help enable great decisions but rarely is that decision squarely in your lap where you have to live with the results. It was something to adjust to.

One of my former guests, Jim Whitehurst, whom I went to business school with, was the President of IBM. Before that, he was CEO of Red Hat. Before that, he was COO at Delta Air Lines. He talked a lot about how, even with a shift from being the COO of a massive organization into being CEO, that there’s nobody behind you. “You have to own it,” he said. Even when he moved to IBM, which is a much more massive company, being the President, he had that safety net of a CEO behind him. It’s a consideration when you move into those top jobs.

It reminds me of somebody. We were starting a family when one of my coworkers told me about having kids. You have your highest highs and lowest lows when you become a parent. In a business career, being a General Manager is like that too because it comes back to your doorstep one way or the other.

When you stepped out of that Stock Plan Services job into the bigger job running Workplace Investing, what were the big things that felt different in that transition?

It’s probably a couple of things. One, anytime time you move up in an organization, you are managing higher-level teams. When you become a senior vice president, you’re managing vice presidents. When you become an executive vice president, you’re managing senior vice presidents. When you become a president, you’re managing EVPs.

You need to step up your game in terms of how you are adding value because those are smart and capable people. There’s an element of that in how you scale yourself and add value at a different level. My job is much bigger in terms of scale. What it pushes you to do is [think about] how you scale your impact through systems and the people because what you can get done in a work week is more limited in terms of what percentage of the organization you can touch or directly be involved in.

”You Click To Tweet. The decisions you make come back to either reward or bite you, depending on how it turns out.” username=””]

It becomes much more a process of thinking about, “Do you have the right management systems in place? Are you looking at the right data? Do you have the right bench strength on your team?” A smaller percentage of what goes on is something you can impact directly. You are working through others throughout your process. You need to be a whole lot more thoughtful about that. Related to that is there’s a little bit of a process where you’ll never understand or know everything. How do you sleep at night and create confidence that things are running well? If they’re not, you will hear about it through all those things I talked about.

When you go from being an individual contributor to a manager, in many cases, it’s easy to do the player-coach thing and still be in detail and know everything that’s going on in the team. When you move up a level, it gets a little bit harder. When you move up a level further, it gets even harder. You get to the point where you are running a big enough organization and realize you can’t know everything. You must rely on the management systems and the people you’ve put in those roles and trust them to do their job. What’s your approach for setting direction and keeping tabs on things as best you can?

In some degrees, it’s situational, depending on the maturity of the team. It’s the maturity in terms of the tenure and stability of the team. How you operate with a new team is very different than with a highly experienced team. If I’m new in a role or picking up new responsibilities, I’ve got a new group I’m working with. With new coworkers, teammates or business, you’re learning. It’s much more than fundamentals and understanding what’s going on every day.

It’s how to manage the short-term, making sure everything is being handled and that you understand the fundamentals of what has to get done. You’re assessing the capability of the people you’re working with. When you get to higher performing teams and more mature management processes and things like that, that frees you up to think a lot more strategically and longer-term. One of the key things that I try to do is spend a lot of time listening.

I travel a lot and talk to a lot of people because a big part of my success is in collecting as much data as I can and synthesizing and integrating it, especially from customers or people who are talking to customers, and also people deeper in the organization where their voice might be getting filtered or for whatever reason might not be getting to me. There are weak signals there that I should be paying attention to. I always try to hold myself accountable for the amount of listening that I’m doing in whatever form that is, either externally or internally. What questions or data you are looking or listening for can vary based on some of those factors I’ve talked about.

Do you have a structured approach for diving into the organization and getting down 2, 3 or 4 levels so that you get more of that frontline perspective? Or is it more happenstance, those interactions?

I had a very structured process prior to the pandemic. We’ve got a number of locations across the US. I was going out to every location at least twice a year and more if possible, as well as to our overseas locations doing lots of round tables. I go to all of our client advisory board meetings, trade events, and do skip levels with people deeper in the organization.

CSCL 22 Kevin | Leading a Large Organization

Kevin Barry on leading a large organization: How you operate with a new team is very different than with a highly experienced team.


That was disrupted by the pandemic. I was starting to build some new routines but they were not as effective. I’m trying to get back to where I was. There’s investing the time in it, which is important. It can’t just be one way, where I’m collecting information. I need to be delivering clarity to the organization about where we’re going, what we’re trying to accomplish, what’s working, and what isn’t.

Thinking a lot about content and how you message to these different audiences is important. I try to have a strategy I can communicate on one page that’s not a bunch of pillars, trapezoids, and PowerPoint, but something that communicates in as few words as possible the essence of what we are trying to do both for customers and our associates, giving them a sense of not just the “what” but the “how” and the “why.” That takes a lot of work and time. I work with my communications or strategy team very hard every year on what that content is to communicate across all those different audiences.

The “why” really matters. I don’t know if you remember this. It was probably 2007 or 2008. Abby was running the former workplace business at that point when it was called FESCO at the time. She talked about the mission of FESCO being to help people be productive at work and prosperous in life. Do you remember that? It was such an elegant and simple definition of like, “Why does this organization exist?”

It captured the role that Fidelity played in helping people with all their workplace benefits but also how that translated to their personal lives. I think about that a lot, having worked in different financial services firms, that “why.” We invest money, but we invest money that people have worked very hard to earn. They need us to do a good job for them. You can’t forget that.

In a lot of our businesses, based on the loyalty of our customers and associates, the more you talk about the “why”, and if they have confidence in the “what” and the “how”, it becomes far less transactional. I know our own associates are not here to collect a paycheck. They want to be part of something important that they feel good about doing and not just for the benefit of Fidelity. That’s a key part of the leadership that sometimes gets undervalued.

You talked about time a while ago. Do you have a mental model for how you try to spend your time across seeing customers, spending time with your direct reports, seeing the team more broadly, working on direction setting, and all of that?

I certainly aspire to. For anybody who’s good at that, I question their adaptability, because things always seem to break down under pressure. I have my assistant color code everything on my calendar so I can go back. In a perfect world, I would be spending 1/3 of my time listening to customers and helping grow the business, 1/3 of my time on products and services, and 1/3 of my time running the business and the administrative. It never quite plays out that way. It’s also seasonal. It varies a lot. If it gets too far out of whack for too long a time, I’m probably not balancing things right. Keeping that balance over the long-term is pretty critical.

Thinking a lot about content and how you message to these different audiences is important. Click To Tweet

What do you do when things start to get out of whack? I’m sure you get pulled in a lot of different directions, as any leader of a big organization does. How do you try and pull it back to more on how you want to be spending your time and more on where you see the priorities for the organization?

One of the things I try to be very disciplined about is, at least 2 to 3 times a year, I have a conversation with my leadership team. I’ve got twelve direct reports and some other folks on a dotted line basis, and we have an explicit conversation about how and what we are spending our time on. The management process is something that should be re-visited. Are you looking at the right data and listening to the right people? Out of those conversations usually comes out where things aren’t getting the attention that they need.

Having the discipline to have an explicit discussion about that a couple of times a year is important. Do you remember the management team you and I were on where there was lots of unscheduled time for conversation? Some of the best stuff comes to light there. If I get in a situation where my team does not have unscheduled time to share the process and raise, debate, and escalate, we are probably on the wrong track.

What do you do to recharge your battery? What do you do to keep work in balance with all those things going on every day?

That’s another thing I don’t have a perfect recipe for. I try to have at least a couple of projects or things that might have nothing to do with work. I’ve been working my way through a Latin cuisine cookbook. I’ve been trying a couple of different genres of literature that I haven’t gotten into before. I’ve been trying for many years and counting to develop a golf game. Some of that also requires some mental discipline too.

If you’re going to be with your family, be present with your family. If you’re going to be cooking, stop worrying about the management review next week and focus on chopping onions. The pandemic made this tougher for everybody, but boundaries are important. If you can keep some boundaries up with your personal life, you’re more likely to recharge when you need to.

Boundaries have been hard during the pandemic era for a lot of people. What’s interesting at the same time is there’s also a hesitance to come back to the office in a lot of companies. It’s a paradox if you think about it. People are saying, “I’m working harder but I’m happier with my work-life balance”, which says something about how soul-crushing commutes are for a number of people.

One of the things I wanted to spend some time on with you is Fidelity and the vantage point that Fidelity has on what people are doing to save for retirement, kids’ education, or whatever. What do you see among the 37 million participants you’re responsible for?

CSCL 22 Kevin | Leading a Large Organization

Kevin Barry on leading a large organization: The more you talk about the why, and if they have confidence in the what and the how, business becomes far less transactional.


There’s a lot going on. It’s interesting. There’s good news and some challenges. One of the good news or trends that I see is, we watch what our customers do in times of market volatility and swings in equity markets, because there’s always a chance for people to make bad decisions, like react to the market to change their asset allocation to react to short-term factors.

We’ve seen less and less of that over time. We saw that through the volatility at the beginning of the pandemic. We’ve seen in the last couple of quarters that people are not reducing their contributions to their 401(k) plans, not making a significant change in their asset allocations, and not taking out significantly higher numbers of loans or hardship withdrawals.

We’re seeing, over time, established savers adopting more of a long-term view, which is encouraging. The other thing that we are seeing is the impact of demographic change in a couple of different ways. We have a whole wave of young workers coming into the economy. They have very different concerns than the Baby Boomers that a lot of the industry focuses on. Millennials and Gen Z are worried about student debt. They don’t plan to stay with their employer all that long or they may want to take a sabbatical for a couple of years to travel or work for a nonprofit.

Connecting with and being relevant for them can be a different thing, but they are often employed by the same company that has lots of pre-retirees. You can’t take a “one size fits all” approach the way you used to. The financial services industry always tends to follow where the money is. Now, the money is with the Baby Boomers or early Gen X-ers like myself, people who have been accumulating and getting ready to move into retirement.

These millions of younger workers entering the workforce have different interests, concerns, and attitudes towards money and consume information differently. They are more likely to go to social media than to listen to CNBC or read the Wall Street Journal. They get ideas on Reddit or TikTok on how to invest. Those are our customers nowadays, and they are going to be the core of our business in the future.

That’s a big focus for us. Also, the American workforce continues to get more diverse across all the ranges of diversity: gender orientation, ethnicity, and a whole bunch of different factors. The financial services industry tends to focus on what was considered a good customer in the past, which is not very diverse. How do you create greater confidence and more relevant offerings for women, people of color, LGBTQ+ customers, and all who are trying to build great financial lives for themselves and their families, but do it in a way where they feel heard, validated, their needs understood, and where they have confidence they’re dealing with the right company?

I tell my folks that we are hired by HR departments, and we are considered an extension of them and their values. If we are not as inclusive or more inclusive than the most inclusive customers we have, then we are not going to be around a couple of years from now, or our competitors won’t either. It’s an incredibly urgent issue in the industry that we are focused on rhat is a big deal.

Boundaries are important. Click To Tweet

How do you respond to that? What does Fidelity do to deal with the diversity in the employment population that’s now part of your 37 million participants?

It takes a couple of different forms. One is, we need to be diverse and inclusive as an employer. When we connect with our customers, we need to look like and show up and be understanding of our customers’ needs. We are a lot more likely to do that if we’re a diverse and inclusive employer, which is a whole range of different work.

In terms of our products, services, and offerings, it requires a lot of learning and customer research: what the different communities or aspects of diversity are, and how they impact people’s financial needs. Everybody is a collection of multiple identities in all different parts of their life. It’s what determines how they think, what they value, and what’s important to them. Everybody is unique.

It takes you down the path of this buzzword that has been thrown around the industry forever, which is personalization. How do you personalize based on somebody’s values, who they are, and what they want, but also do that in a way that’s not creepy, where you know [only] what they want you to know about them? We’re spending a lot of time on research. There are obvious things like multilingual websites or accessible channels for people with visual or hearing differences.

It’s stuff like that where the limitations are more apparent. “What does your advertising look like? What language do you use? Are you speaking to an individual or the whole family?” Those are all questions we’re wrestling with [as well as] how to take one approach versus another in terms of what makes a customer most confident. Those are tricky issues. The worst thing to do is take a “one size fits all” approach to any of this, that all women want X or customers want Y. We tailor it.

It’s hard to strike that balance between trying to adapt without it coming across as condescending, creepy or whatever word you want to use.

We’re getting data [in managing their savings] that they don’t want us to [use more broadly]. One of the big areas we’re thinking a lot about is privacy and data management in this whole space.

CSCL 22 Kevin | Leading a Large Organization

Kevin Barry on leading a large organization: How the senior team and the broader organization its time is something that should be regularly re-visited.


You’ve got arguably one of the biggest troves of personal data out there.

You can access other forms of data externally, but our clients don’t want us to do it, and employees want us to know that. It’s a fascinating space.

How are COVID, workforce dislocation, and now inflation affecting what you see in terms of people’s saving behavior?

We have been tracking this very closely, as you would expect. There was a bit of a shock wave at the beginning of the pandemic when there was a spike in unemployment, the CARES Act was passed, and people could take a couple of thousand dollars out on a penalty-free basis. Employment bounced back pretty quickly. Lots of stimulus dollars got into the economy, which stabilized savings. Savings jumped quite a bit in the overall macro economy. The biggest long-term impact we are seeing is what’s happening with the labor market, the competitiveness of the labor market, the war for talent, and how that has gone off the charts, especially in the areas like technology and some specialized skillsets.

Our clients, as well as us as an employer, are in a real scramble to understand how you differentiate yourself as an employer and what role compensation and benefits play in that. There’s certainly wage inflation in technology, AI, data engineering, and all these fields. Is there a different range of benefits that are needed? Student debt management is a fast-growing field. There’s a whole range of voluntary benefits that some companies are experimenting with. Some of which are interesting. We probably won’t get into the pet insurance business, for example, but that’s a hot one now. There’s no silver bullet out there.

All our clients are talking to each other and us and saying, “What are you trying? What’s working for you?” It’s the constraint or lack of key talent, and whatever role the pandemic played in that, whether it’s made people question their choices in life and maybe tightened up the labor market, with lots of people exiting the labor market, or accelerated the need for technology, products, and services. I’m not exactly sure what the exact cause and effect are but I know there is something that the pandemic triggered in terms of how the labor market looks versus a few years ago. Savings behaviors are as healthy as they were in general, but employers want more in terms of attracting talent than just a decent 401(k) plan.

What advice would you give people who are thinking about how to save for retirement, education, buy a house, pay down student debt, credit card debt, whatever? We’re not going to stray into the formal definition of “advice and guidance” on the show, but perhaps som general Fidelity wisdom that you can dispense.

The American workforce continues to get more diverse across all the ranges of diversity, gender orientation, ethnicity, and many other factors. Click To Tweet

Any financial planner would tell you this. First of all, take advantage of any free money that’s available, that employer match or contribution to a health savings account. Employee stock purchase plans with a big discount feature are another great way to take advantage of things like that.

Maxing out your savings may not fit with your day-to-day financial needs either. You have to have a balance. You have to be able to live your life in a sustainable way, as well as save for the long-term, have a consistency of saving in whatever form it takes and not making radical changes, not panicking, and seeking good financial advice from whoever provides it to you. Those are all good ideas.

Let’s go back to the beginning of your career. You went to Harvard undergrad. You majored in Government. How did you decide to major in Government? What did you see yourself doing at that point when you were looking ahead to graduation from your undergrad program?

As I recall the process, as my 18 or 19-year-old self, I don’t think I was thinking too analytically about it. I’ve got a high degree of intellectual curiosity. I’m curious about how things work and why things happen, but not necessarily in the technology, engineering, or sciences sense. I’ve always been a little bit of a political junkie, even when I was a kid. Government, which is Harvard’s way of describing Political Science, is a field of Sociology that gives you frameworks for thinking about how the world operates.

I’ve also found that it has given me some ways to think about big organizations, whether they are governments, large corporations – my own corporation or competitors – and how you think about, “Why things are happening the way they are? what’s intentional and not intentional, and what’s driven by schedules versus leaders versus processes or biases?” I gravitated based on what I enjoyed learning about. I wasn’t giving any thought to what I was going to do after college at that point.

What did you end up doing when you left college? You eventually went back and got your MBA, but in that in-between period, what were you doing?

I ended up joining the Central Intelligence Agency. I was an Intelligence Analyst in Langley, Virginia, for five years. I wasn’t a particularly strategic thought process, but the one thing I knew coming out of college was that I enjoyed government. I didn’t want to go to graduate school. I didn’t want to join the Foreign Service in the State Department, ad I had a serious girlfriend, now my wife of many years. I thought, “Who would pay a BA to do Political Science?” I put out an application, and that’s where I worked. I loved it.

CSCL 22 Kevin | Leading a Large Organization

Kevin Barry on marketing to a diverse customer base: The worst thing to do is take a “one size fits all” approach


That was at a time I remember them coming to campus at Duke, where I went to school undergrad. They recruited very heavily at the time, but they also were living down the sins of the past, particularly around what had gone on in Nicaragua and the Iran-Contra situation and all of that. For somebody who is a political junkie, [the CIA] was undoubtedly a good place to go. There were a decent number of people at McKinsey when I worked there who had been analysts at the CIA. It became its own proving ground for people.

They teach you, regardless of what specific area you work in. I worked in an area I had never studied and had to learn, but they gave us tools and frameworks, and importantly, taught us how to communicate, be concise, and get to the point quickly. There were length and format requirements for how you gave oral briefings to busy policymakers. There were some pretty transferable skills to the business world.

How did you decide that you were going to go back and get that MBA?

I always knew I didn’t want to spend my entire career at the CIA. The longer you stay, the harder it is to make the jump. You just get more specialized, and your networks change over time.

It’s narrow. That’s one of the challenges the government sector is facing. You have a narrow lens on things.

At that time, there was a health issue in our family. We were focused on getting back up to the Northeast with our extended family. That was a geographic focus. My dad was a career business executive. I’d grown up hearing about what he talked about and what he was interested in. It felt like something I could relate to. We had started a family very young. We had two little kids when I was applying to business school. I wanted to be able to provide for them over time. No offense to lawyers, but it sounded more fun than law school, so I ended up in business school.

How did you end up leaving there and heading into the finance world? You were at Frito-Lay first.

Knowing yourself and what you want is important. At best, at any point in time, knowing what's important to you is important. Click To Tweet

It’s an interesting story. I studied to be a brand manager. To be a brand manager, I did my summer internship at Ford Motor Company in brand management. All the companies I interviewed with were in brand management, except for PepsiCo. They were talking to me about a job in strategy and planning. They said, “Don’t worry. If you do this job, you can get into marketing.” They were the coolest, smartest, most interesting people I talked to, with products that are very easy to relate to. I went to PepsiCo. Four weeks in, I found out, to my surprise, that it was a hardcore corporate financial planning job that I was not equipped or trained to do. I was at risk of failing pretty badly.

I had signed a lease and already had a third kid on the way, so I had to make this thing work. I became self-taught in finance, pulled out all the books I’d ignored in business school, and did a self-taught crash course in Corporate Finance with a lot of help and advice from friends, coworkers, and bosses. I found out that I liked it. It was probably poor planning on my part, a little bit of serendipity that I stumbled into something I could figure out that I ended up enjoying.

Everybody I talk to would say there’s a certain amount of opportunism, serendipity, and everything [like that in career choices]. You were in the finance role at PepsiCo, Frito-Lay, Gillette, and Fidelity. How does finance work in those three places? What’s similar and different?

The work of finance tends to reflect the business model in a lot of ways. PepsiCo, at the corporate center, is a diversified conglomerate. I spent a lot of time on things like capital allocation, investment analysis, and things like that. Frito-Lay is in a short cycle, direct store delivery business, with products that are perishable. When I was there, it was short-term focused. I spent enormous amounts of time on logistics, weekly sales forecasts, and how you move things in a rapid time from the corn and potato fields and onto store shelves, and how you prevent them from going stale.

The work of finance at Gillette was around the manufacturing and logistics process. Gillette was a consumer product that makes health and beauty aids, like manufacturing-intensive Oral-B razors, Fusion, vibrating five-blade razors, and things like that. It’s a very global business. I spent a lot of my time there thinking about that. It was still in logistics but global logistical supply chains and how you manage across 80 different markets with things like foreign exchange exposure.

Coming to a place like Fidelity, we’ve got tens of millions of customers, where we service their needs every day. That servicing often happens on massive IT infrastructure platforms and with people on the front end trying to provide service. This has threaded through my career of managing customer service and logistics, but in the case of Fidelity, it’s about phone and platform capacity.

They [the finance function] are still worried about service levels and forecasting, but it takes different forms based on what you’re delivering, how it’s delivered, and the timeframes you are dealing with. The one other thing I would mention that’s different, and you probably would agree with this, is working at a private company versus a public company. It’s hard to overstate what a difference that is.

CSCL 22 Kevin | Leading a Large Organization

Kevin Barry on the finance function: The work of finance tends to reflect the business model in a lot of ways.


In your case, it’s not only in a private company, but a family-owned company. It’s a very different proposition than a lot of other private companies. When I went from Fidelity to State Street, it was “night and day” different.

It’s how decisions get made, how capital is allocated, and the timeframes. In Frito-Lay, if we miss the weekly sales forecast, that was a big problem. We make decisions here on a much longer timeframe. We still need to be disciplined and be data-driven and analytical, but we’re less driven by the struggle of the week, month or quarter. We tend to look at much longer timeframes, which is a pleasure compared to a more short-term focus [that comes in being in most public companies].

You mentioned you were trying out some new book genres. What are you reading these days?

It’s a couple of different things. I’m trying some much older stuff. I spend some time on Cape Cod in the summer. I dug out a copy of Henry David Thoreau’s Cape Cod, which was written back to the 1850s. I have an architecture book about Soviet subway stations, CCCP Underground. It’s about public art and how civic values get represented through architecture, in this case, through subway stations. I don’t know why I like it, but I do.

I’ve been trying to learn about diverse communities and parts of society that aren’t part of my own history. I’ve been reading a lot of Colson Whitehead. He’s a phenomenal author who writes great novels, but a lot of it is about the Black experience in America. The one that I’ve cracked is called Harlem Shuffle, about gangsters in Harlem in the early 1960s. I’ve got probably 3 or 4 others that are stacked up in the rotation waiting to be opened.

Any final career advice you would offer to people reflecting on how things have gone for you and what you’ve learned over the years?

I’m closer to the end of my career than the beginning. I would say from my vantage point that people’s careers cause them a tremendous amount of anxiety. They worry if they have the perfect plan and are doing all the right things. Knowing yourself is important and what you want. At least at best, at any point in time, knowing what’s important to you is important.

Accept that some parts of your career you’re not going to be able to control, but just make the best decisions you can at any one point in time. There are curve balls in a negative way but also that could be some of the best surprises. I never expected to be where I am now and am having the time of my life doing it. I’m very lucky but I would never have predicted, back in the late ’80s coming out of college, that this is where I would be, and that I would be enjoying the ride.

People have multiple careers over the course of their career, much more so than they used to. The beauty of that is that you don’t have to feel like you are locked into something forever. The outcome of it in both our cases is you end up someplace that’s very different from where you started and some place that you probably didn’t anticipate being in at the beginning.

Kevin, I appreciate the time. It has been good to catch up. I will hopefully see you back in the US at some point when I get back to Boston. Have a good rest of your day. Take care.

Thanks again to Kevin for joining me and sharing his career story and learnings. If you are ready to take control of your career, visit If you would like more regular insights, you can become a PathWise member. It’s free. You can also sign up on the website for the PathWise newsletter and follow PathWise on LinkedIn, Twitter, and Facebook. Thanks, and have a great day.


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About Kevin Barry

CSCL 22 Kevin | Leading a Large OrganizationKevin Barry is the President of Workplace Investing at Fidelity, a role he has held for the past 5 ½ years. If Fidelity administers your 401k, 403b, stock plan, pension, medical benefits or HR / payroll benefits, all of that falls under Kevin’s remit. Kevin joined Fidelity 16 years ago and came up through the finance function before becoming the head of Stock Plan Services and then moving into his current role.

Prior to joining Fidelity, Kevin was in the finance function at Gillette, and prior to that he was in the finance function of Pepsi’s Frito Lay division. He started his career as an analyst with the Central Intelligence Agency.

Kevin is a Trustee of the Boston Ballet and is a Seven Generations Board Member for City Year. He earned his Bachelors’ degree in Government from Harvard University and his MBA from Dartmouth’s Tuck School. He and his wife Patti live in the Boston area and are the parents of 4 adult children.


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