
Loading summary
Thomson Reuters Announcer
This podcast is brought to you by Thomson Reuters. The best don't just do their work, they change what's possible. Cases won, audits completed, jobs saved. Behind every one of those moments is a professional who needed to get it right and did. Thomson Reuters builds the technology that sharpens insights, speeds up decision making, and powers the outcomes that matter. So when professionals act, the impact is felt by everyone. Be a change maker visit tr.com changemakers
Stamps.com / Progressive Advertiser
still waiting in line Again, that's time you will never get back. Save time and money with stamps.com over 4 million businesses have skipped the line with stamps.com join them to save up to 90% off carrier rates from your computer or phone right now. Print postage for certified mail, registered mail and packages in seconds. Then schedule a pickup right from your home or office for a limited time. Go to stamps.com and use code podcast for a free welcome gift. Taxes and fees apply.
Greg Kilstrom
Hi, I'm Greg Kilstrom, host of the Agile Brand, and here's a question for you. What if the biggest barrier to your company's transformation isn't your legacy technology, but your legacy thinking about it? Today we're at Pegaworld 2026 at the MGM grand in Las Vegas and we're going to talk about the immense challenge and opportunity to of enterprise modernization. Specifically, we're going to cover translating a massive technology initiative into tangible improvements in the customer and partner experience, the practical steps required to make an enterprise AI ready by bridging the gap between legacy systems and modern cloud platforms, and how transforming core operations can directly enable marketing and product teams to accelerate speed to market.
Greg Kilstrom (Host)
Welcome to Season eight of the Agile Brand Podcast. This season we're going all in on expert mode, Martech AI and customer experience, talking with the people and platforms behind
Greg Kilstrom
the brands you know and love.
Greg Kilstrom (Host)
Again, I'm your host Greg Kilstrom and I help Fortune 1000 companies make sense of MarTech AI and marketing ops. Hit subscribe or follow to make sure you always get the latest episodes and leave us a rating so others can find us as well. Pega provides the leading AI powered platform for enterprise transformation. The world's most influential organizations trust Pega's technology to reimagine how work gets done by automating workflows, personalizing customer experiences, and modernizing legacy systems. Since 1983, Pega's scalable flexible architecture has fueled continuous innovation, helping clients excel accelerate their path to the autonomous enterprise. Learn more@pega.com tell me to discuss this
Greg Kilstrom
topic, I'd like to welcome Shelia Anderson, evp, Chief Information and Digital Officer at unum. Shelia, welcome back to the show.
Shelia Anderson
Thank you. I'm glad to be here.
Greg Kilstrom
Yeah. Good to talk with you. Great keynote this morning.
Shelia Anderson
Thank you.
Greg Kilstrom
Great to have you back on the show. So it's been a couple of years, but great to see you. Before we dive in, why don't you give a little background on yourself and your role at unum?
Shelia Anderson
Of course. So I am actually in a new role at Unum. I have been there for 12 months. I'm the Chief Information and Digital Officer, which basically means I have responsible for all technology for Unum Group.
Greg Kilstrom
Great, great. So we're going to. And actually maybe just a little background on Unum as well for those that are less familiar, you know, what's the company do, who are its, its customers and things like that.
Shelia Anderson
Absolutely. So Unum Group is a 175-year-old company focusing on the employer benef. So think of services like leave and absence management, long term disability, all of those group types products that you would purchase through your employer or at a work site.
Greg Kilstrom
Nice, nice.
Greg Kilstrom (Host)
Okay, great.
Greg Kilstrom
So let's dive in then. And you know, caught your keynote this morning. It was definitely an amazing story. I know that a lot of companies are facing similar enough challenges here and you know, your keynote was titled COBOL meets Cloud. So maybe walk us through for those that weren't able to catch it, what was the business problem, customer experience problem that Unum identified that made this modernization not only necessary, but necessary, I guess.
Shelia Anderson
Absolutely. Thank you for that question. First of all, part of what we were looking to solve is really addressing two things. One was a need for, for our business to be able to take advantage of some of the new and emerging capabilities, specifically in our claims process, how we service those customers through the claims experience. The other part that's more internally focused for us was to be able to prove out methods that we could actually use as more of a mainframe modernization strategy that would be broader than the one focused area for claims. So those are the two objectives that we had when really looking at how do we go about solving for this was really one to focus on that customer experience lens and then the second one, which is also a key more internal focus goal for us, which was to look at what might we be able to prove out as we look at our mainframe modernization strategy for the future and how might we choose to exit the mainframes, which for us it's leapfrogging.
Greg Kilstrom
Yeah, yeah. I mean, because, yeah, the mainframes, they don't just handle one part of the processes, correct? Yeah, yeah. And I mean I think the, so some of this, obviously there's a lot of technology involved, there's a lot of data involved, but there's also a mindset shift as well in just kind of how people think about legacy systems and how they think about their solutions. Can you maybe talk a little bit about that part of what kind of mindset shift is required to really do that?
Shelia Anderson
Absolutely. And I'll tie that into our broader strategy as a company. So in the year that I've been there, we've absolutely started focusing on much more of what I'll call business aligned value creation through all of our investments in technology. So that really doesn't start with technology. It starts with our business focusing on making sure that we're solving for the biggest opportunity business challenges. And so that that means really looking at how we prioritize the work that we're doing, saying no to the things that aren't going to yield the greatest value in our business. So that's a bit of a new muscle for the company too. That's not even related to technology. It's related to how do we choose what, what we're going to invest in from the beginning.
Greg Kilstrom
Yeah, yeah. Well, and to that point too, you know, modernization products projects often get bogged down in trying to boil the ocean. Right. So it's why, you know, why start with one thing? Why not, you know, everything needs to be modernized. Right. So you know, you mentioned, you know, starting with a few things, how did you prioritize which barriers, you know, like the claims processing and things like that to tackle first and you know, possibly to show early value as well.
Shelia Anderson
Sure. And it's just that we prioritize it based upon the business aligned value in the future. We're actually aligning as a business to value streams. So we do have a front to back ownership from our business of each of those key value streams across the company and the associated technology investments that go into that. So that's really how we're choosing where we place our bets, where we place our investments. And one of the biggest shifts is actually measuring the business outcomes so that we have the offsetting benefit that's expected relative to the investments that we're making in technology people and process.
Greg Kilstrom
Yeah, well, and I would imagine that starting that outcome measurement with a smaller scope, I mean that you can course. Correct, right? You know.
Shelia Anderson
Yeah, exactly. And, and there's just not the, the tolerance anymore for multi year, three to five year longer term investment journeys. That have longer term, longer tails on actually receiving the return on that investment as well. So I think that's one of the biggest shifts that you're starting to see with AI, the opportunity to, I call it peeling the onion approach. So you're actually able to start figuring out how can you decouple and minimize the dependency on the mainframes while still leveraging the data layer. If you think about API strategies of the future, I think that's going to be much more prevalent as you start to see companies peeling away and owning the customer experience layer, maybe in a different way, and moving more to a data layer that provides you access to all of the data that's embedded in the legacy systems.
Greg Kilstrom
Well, and I think that that touches on. One of the things you mentioned in your, in your keynote was just, you know, the business has to keep moving, right? I mean, customers keep having claims.
Shelia Anderson
It doesn't stop, it doesn't stop. And I think that's one of the finest. The biggest challenges to me is the business is, is still moving along while you're doing all this work. And so I always equate it to you're flying the plane to a destination, but you're changing out the interior of the plane, knowing you have to land it. And it's very much the same in a business as we're looking to change our internal, whether it be people, process technology. But you still have to deliver today. So you have to honor the commitments today while you're actually redefining tomorrow.
Greg Kilstrom
Yeah, yeah. And so, you know, certainly AI is a big part of that. And even the people and process part is related to how they use AI. Or not in some cases. But so this phrase AI ready is used quite a bit, but can often feel abstract. What does that mean for a company like Unum to be AI?
Shelia Anderson
Thank you for asking the question. I love this because it's absolutely not abstract. I would say you have to take a very intentional approach to being AI ready. And so for us, we've separated it into two primary categories and I'll talk about both of those. One is what I call everyday AI for the broad employee population. And for example, how we actually implement that. We actually have training curriculums that we are rolling out to the entire company. We've rolled out things capabilities like Copilot. So we're actually encouraging citizen development throughout the enterprise. We're putting the right controls in place to manage that and we'll continue to monitor that as it evolves. So that's definitely when you put that in the Category of how do you start moving your whole company forward? You do have to be very intentional to educate, to take the fear out so that the broader employee base can start interacting with and understand the value that they can get. And at the end of the day, they're going to be better and their jobs will be better if they're able to see the value coming through in the work that they're doing every day and bringing forward those recommendations. On the other side of that is what I like to call more of the customer embedded AI. Much of that does require more of a deep engineering skill set. And for example, inside of engineering this year when I came in, we actually established a goal so that 100% of my engineering staff would be fully trained in leveraging AI in their daily work. And so we're seeing the productivity and the outcomes coming out of that. That's definitely something that you have to do very intentionally. We've made available those training programs and it's something that we're embedding in how we're working. So I think the shift for me is AI ready for means really enabling both your broad employee population as well as your subject matter experts, whether you be an engineer, our customer experience, our product owners, even our folks in our operational side of the business. For example, my peer Andrew runs our customer operations function. He and I are tightly integrated in how we look at our combined strategies together so that as we look at investment in technology, we have the offsetting value that actually is being measured and the outcomes are being measured in the operations as well.
Greg Kilstrom (Host)
You know that moment when marketing wants a landing page, design mocks it up and engineering says, yeah, we'll get to it. Thousands of businesses, from early stage startups to Fortune 500s are choosing to build their websites in Framer, where changes take minutes instead of days. Framer is a website builder that works like your team's favorite design tool with real time collaboration, a robust CMS with everything you need for great SEO, and advanced analytics that include integrated AB testing. Your designers and marketers are empowered to build and maximize your dot com. From day one, changes to your Framer site go live to the web in seconds with one click without help from engineering. Framer is also an enterprise solution, giving brands like Perplexity, Miro and Mixpanel the confidence they need to build their websites in Framer. Learn how you can get more out of your.com from a framer specialist or get started building for free today@framer.com agile for 30% off a Framer Pro annual plan that's framer.com agile for 30% OFF off framer.com agile rules and restrictions may apply.
Stamps.com / Progressive Advertiser
Insurance isn't one size fits all. That's why drivers have enjoyed Progressive's name your price tool for years now. With the name your price tool, you tell them what you want to pay and they'll show you options that fit your budget. So whether you're picking out your first policy or just looking for something that works better for you and your family, they make it easy to see your options. Visit progressive.com, find a rate that works for you with the name your price tool. Progressive Casualty Insurance company and affiliates Price and coverage match limited by state law
Greg Kilstrom
so let's talk a little bit more about the measurement then. Certainly that sounds like a key approach and something that you approach from the start, which is I think, the right way to do it. What does that look, there's always going to be the traditional metrics of the business and those likely wouldn't change. But what are the KPIs that go into measuring success?
Shelia Anderson
Sure. And I will say it's going to depend, of course. So generally, for example, in the work that we've done with Pega, because that is focused on the claim side, we look at the claims process. What you would do is look at the actual process end to end view of the process that you're automating or solving differently and then look at what is the business outcome that you want to measure against that process. So in the claims journey for us, it's customer satisfaction, average handle time, for example. A lot of that also ties in with a lot of the other metrics that we have in our contact center. So you would look at the specific business process and that will vary. Honestly, gone are the days of simply reporting the internal IT metrics, we still do those so that we can see improved productivity on an agile squad, for example. But the ultimate outcome is the outcome that you're driving for the business.
Greg Kilstrom
Yeah, yeah. And then, you know, I know you talked about the training aspect and you know, obviously that's a key part in getting teams involved. How, how do you think about measuring that? Is it, is it adoption? Is it, you know, how, how do you measure your success there?
Shelia Anderson
Well, I think the truest measure of success is when you see people actually able to put to value what they're learning in their work every day. Yeah. So do we have specific concrete measures where we're able to measure that today? Not today? I think that's something that will absolutely evolve to Part of where we're wanting to go is to really get to a more empowered approach and really centered around learning, where people see the value of learning new skills and they're able to put that to work and see the value come back into the business as well.
Greg Kilstrom
Yeah, yeah. I mean that's something I've definitely heard from many others. And once they kind of hit get past some, you know, initial, you know, initial hurdle, a lot of employees are actually, they're more motivated to do.
Shelia Anderson
They are and it's. And of course we've seen, we do measure it, for example. So in some of the broadcasts, education and training, just as an example where it didn't work and where you have to learn from it is we made available a lot of training broadly across the organization. But in the early days what we saw was that there really wasn't an adoption of that. So we do look at adoption. And so as an executive leadership team, we're looking at. So how do we encourage. Maybe we need a little bit more of an intentional push rather than a pull, which is how we had first approached it, which was create the training and all of them will come. Well, you're not always going to see that. So you may have to revisit that and then come up with a little bit of a different plan to incent those behavioral changes and really to create more of a learning culture inside of your organization. Because it's a big shift. We're 175-year-old insurance company, we're in the business of managing risk. And all of a sudden now we're introducing this new concept called AI and that can be a bit scary to anyone in an average role on the floor doing their job.
Greg Kilstrom
But I mean, it's an Inspiring story for 175-year-old company in a very, you know, highly regulated, risk averse organization to make such strides. And I know there's more, more to come as well, but.
Shelia Anderson
Exactly. And that's why the education I think is key. And you just can't underestimate the number of conversations that you need to have, the more kind of informal approaches to do that. I'm a big believer in getting the advocacy across your business. So we actually do have an AI champion and advocacy program where we're looking to deeply embed AI advocates inside of our business to help with that adoption inside of the business because it needs to be a little bit of a groundswell effort where your business sees the value to actually adopting the capabilities that you're making available.
Greg Kilstrom
And there are going to be some People that are, they're going to rush to. You know, there's some people that just want to be the early adopters. Right. And there's others that, you know, sit back for a little. I've been, I've played both, you know, over the years, so. Yeah, yeah, definitely. So, you know, for. Based on your success as well as even some of your learning so far, what would your advice be to, let's say, for an organization that isn't quite as far along in their transformation, but has that legacy tech debt, the mainframes, all of that stuff, what would your advice be to them as they're getting started, but maybe feeling a little overwhelmed?
Shelia Anderson
My biggest piece of advice is just get moving. So put your toe in the water before you know that you can swim, for example. This is one of those things that you're going to have to take a test and learn approach to and you'll see that comfort and that confidence building as your, as your team start working through that. So definitely get started. It doesn't have to be perfect. That was part of my message this morning. I really believe that just getting started, having some intentional focus on understanding what it is that you want to prove out, you don't have to know the exact way that you're going to complete it, but at least have a vision of where you want to go and what you want to prove out and then get started. Just move.
Greg Kilstrom
Yeah, yeah. Love it. So as we wrap up here, just a couple, couple last things I do also, you know, we're here at PEGA World, want to talk a little bit about. I know you touched on a little bit, but, you know, what exactly was the role of PEGA in this transformation? You know, where does that, where do they play a role?
Shelia Anderson
Yes. So for us, we actually were leveraging PEGA as part of our case management processes already. So we already have a long standing relationship with pega. But because I went back to saying we wanted to prove out the specific AI capabilities, leveraging the AWS Transform piece to actually interrogate the 1.5 million lines of code for this specific situation and then leveraging PEGA blueprint to actually create that workflow reimagined view. So that's the role where we leverage PEGA to, to play that secondary part around the blueprint.
Greg Kilstrom
Got it. So blueprint, you were able to essentially, and for those that are less familiar with blueprint, you're able to reimagine your workflows.
Shelia Anderson
Just think of it as taking your workflow. We were able to almost reverse Engineer, if you think about it. So really understanding the embedded COBOL logic and then reimagining that into the workflows of the future as your starting point. So you feed that into the PEGA blueprint approach.
Greg Kilstrom
Nice. I love it. Well, a couple, couple things here. What's been a highlight of pegaworld for you so far?
Shelia Anderson
The biggest highlight for me, honestly is just the knowledge sharing that goes on and getting to see a lot of peers and then of course, individuals that have worked with me before. I love hearing about what they're doing. And for me, I have had the opportunity to work for a number of companies and one of the big things for me is you always want to leave any company well, so I love hearing their wins as much as what I'm doing today with UNUM Group. So that's really a special part of being able to come and participate and hear all those great stories too.
Greg Kilstrom
Yeah, that's great. Well, thanks so much for joining. Very last thing for you. I like to ask everybody, what do you do to stay agile in your role and how do you find a way to do it consistently?
Shelia Anderson
The way that I stay agile is a lot of participating in conferences like this, staying plugged into my network. I do a lot of networking in the CIO community so that we're all knowledge sharing around what's coming, how are we solving for it. And I do regular sessions, group sessions usually, and stay current with that. I do a lot of reading, I listen to a lot of podcasts, I listen to yours, and so I stay current in that way. It's important.
Greg Kilstrom
Yeah, love it. Well, again, I'd like to thank Celia Anderson, EVP Chief Information and Digital Officer at Unum, for joining the show. You can learn more about Shelia and Unum and Pega by following the links in the show notes.
Greg Kilstrom (Host)
PEGA provides the leading AI powered platform for enterprise transformation. The world's most influential organizations trust pega's technology to reimagine how work gets done by automating workflows, personalizing customer experiences, and modernizing legacy systems. Since 1983, Pega's scalable, flexible architecture has fueled continuous innovation, helping clients accelerate their path to the autonomous enterprise. Learn more@pega.com and thanks again for listening to the Agile Brand podcast. If you liked the episode, hit subscribe and drop a rating so others can find the show too. And if you're interested in consulting, advisory work, or if you need a speaker for your next event, feel free to reach out. Just visit GregKilstrom.com that's G R E G K I H L S t r o m.com the Agile brand is produced by Missing Link, a Latina owned, strategy driven, creatively fueled production co op. From ideation to creation, they craft human connections through intelligent, engaging and informative content. Until next time, stay curious and stay agile.
Shelia Anderson
The Agile Brand.
Thomson Reuters Announcer
This podcast is brought to you by Thomson Reuters. The best don't just do their work. They change what's possible. Cases won, audits completed, Jobs saved. Behind every one of those moments is a professional who needed to get it right and did. Thomson Reuters builds the technology that sharpens insights, speeds up decision making, and powers the outcomes that matter. So when professionals act, the impact is felt by everyone. Be a changemaker visit tr.com changemakers you're
Stamps.com / Progressive Advertiser
listening to this podcast, so I know you've got a curious mind. Here's a helpful fact you might not know yet. Drivers who switch and save with Progressive save over $900 on average. Pop over to progressive.com, answer some questions and you'll get a quick quote with discounts that are easy to come by. In fact, 99% of their auto customers earn at least one discount. Visit progressive.com and see if you can enjoy a little cash back. Progressive Casualty Insurance Company and affiliates national average 12 month savings by $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025. Potential savings will vary.
Episode Title: From PegaWorld: Unum CIO & CDO Shelia Anderson on AI-augmented enterprise modernization
Release Date: June 19, 2026
Guest: Shelia Anderson, EVP, Chief Information and Digital Officer, Unum
Host: Greg Kihlström
Location: PegaWorld 2026, MGM Grand, Las Vegas
In this episode, Greg Kihlström sits down with Shelia Anderson, Chief Information and Digital Officer at Unum, to explore the challenges and opportunities involved in large-scale enterprise modernization within a 175-year-old, risk-averse organization. The conversation focuses on Unum’s cloud and AI transformation journey—from legacy mainframes and COBOL to modern platforms and customer-centric innovation. Anderson shares practical insights for bridging legacy technology with next-generation tools, building an “AI ready” culture, and demonstrating true business value through measurable outcomes.
On Value-Driven Technology:
“...that really doesn't start with technology. It starts with our business focusing on making sure that we're solving for the biggest opportunity business challenges.”
— Shelia Anderson (05:56)
On Modernization While Maintaining Operations:
“You have to honor the commitments today while you're actually redefining tomorrow.”
— Shelia Anderson (08:56)
On Real AI Readiness:
“It's absolutely not abstract. I would say you have to take a very intentional approach to being AI ready.”
— Shelia Anderson (09:52)
On Learning Culture:
“You just can't underestimate the number of conversations that you need to have, the more kind of informal approaches to do that. I'm a big believer in getting the advocacy across your business.”
— Shelia Anderson (17:16)
On Getting Started:
“My biggest piece of advice is just get moving... It doesn't have to be perfect.”
— Shelia Anderson (18:30)
This episode offers a real-world blueprint for modernizing legacy enterprises, emphasizing business-aligned strategy, a dual-pronged, intentional approach to AI readiness, and a culture of agility and continuous learning. Anderson’s experience at Unum illustrates that successful transformation is as much about people and mindset as it is about technology, with measurable business value as the north star.
For further resources and links related to Unum, PEGA, or this episode, check the show notes or visit Greg Kihlström’s website.