When Dean Del Vecchio joined 159-year-old Guardian Life Insurance as a top executive five years ago, he discovered that the company’s first policy-administration system was still functioning.
“In 1967, before we put a man on the moon, we built our first policy-admin system. I like to say the good news is it’s still running and the bad news is it’s still running,” Del Vecchio said with a laugh in a phone conversation last week.

Today, Guardian is, like all big companies that have been around a while, still working through some legacy issues. But it has made massive strides toward becoming a fully modern and customer-centric insurance company that can compete with the lightning-quick startups while also maintaining the size, relationships and financial heft of a market leader.
“Being 158-plus years old comes along with a lot of legacy technology and what most people refer to as technical debt, and this was no different when I came onto Guardian about five years ago,” said Del Vecchio, who is executive vice president and not only CIO but also the company’s chief of operations.
Transformation at Guardian: Putting Customers First
“When you think about doing a digital transformation and you have systems that were built—again—in 1967, we have a lot of monolithic systems still running and still need to run to service the existing business as we make this transformation.”
Then Del Vecchio expressed an idea that shows just how sweeping the changes he’s helping to lead at Guardian truly are. Because “exceptional and delightful customer experience” is not typically an outcome associated with the life-insurance business.
“At the same time, we’re also going into this digital transformation and into this consumer-facing customer experience that everybody’s looking to provide, this exceptional and delightful customer experience,” said Del Vecchio. He also later said that his team’s goal is to make those experiences “easier, more pleasurable and more delightful.”
“But clearly it’s a challenge to do that when you’re trying to operate a legacy platform, transfer to the cloud, and put a front end on these things that have to still attach to a back end that was not designed for the type of transactions and experiences that people are looking for today.”
Transformation at Guardian: Competing for Digital Simplicity
To overcome that challenge, Del Vecchio and his team knew they’d have to strike exceptionally strong relationships with strategic technology vendors. Amazon Web Services has emerged as Guardian’s leading cloud partner in planning and executing this massive overhaul of not only Guardian’s technology but also its processes, capabilities and its culture.
Because the competitive landscape Guardian finds itself in today is radically different than anything the company’s confronted before, Del Vecchio said.
“The way I’ve described it is: we’re not competing with just our peer group of competitors that you would think about—other insurance companies and financial institutions. We’re competing with an individual’s last digital experience.
“So whether it be a purchase they just made or another company that they just had a service experience through, we’re trying to modify and modernize our platforms to provide the same type of experience you would expect for any digital transaction,” he said.
“We’re competing with customer experience—that’s what we’re competing with.”
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Transformation at Guardian: Partnering with AWS
AWS has played a huge role in helping Guardian be able to live up to that new standard, Del Vecchio said.
The partnership with AWS went far beyond the technical prowess and cost advantages for which AWS is typically known. It extended into deep explorations into Guardian’s business models, operating philosophies, culture and desired outcomes.
As Del Vecchio described the relationship, it become clear that he values AWS as much for what it knows and how it thinks as for its market-leading cloud services.
“They’ve been actually a great partner. We do these ‘innovation challenges’ with our partners, but we also have a pretty formal program in how we define who’s going to be strategic, who’s emerging, who’s transactional, or value-type partners.”
And for the past two years, AWS has won Guardian’s “CIO Award” for being the best and most-innovative partner.
“We share with them everything about us,” Del Vecchio said, so that “before we go and do an EBC visit with them, they could be very targeted and tailored on where they think they can add value and help us meet our goals and deliver our promises for our consumers.
“Over the last couple of years, we spent the first year preparing the environment at Amazon, and then we took a production-first approach to migrate our platforms over there,” he said.
“And they provided very senior architects and engineers to help us design the solution that would make sure—because we operate in a very highly regulated industry—that we were comfortable moving our admin systems there and some of our customer facing type systems there.”
Transformation at Guardian: Co-Creating Products and Processes
During that journey, Del Vecchio said, the Guardian and AWS teams identified technology gaps between what they already had and what they needed to reach the desired end-state.
“And AWS really stepped up and helped us co-create products to make sure that we were going to be able to satisfy the regulatory requirements that were required. AWS has been there the whole way with us.”
Six months ago, that journey marked a major milestone when Guardian was able to to get out of the business of owning and operating its own data centers—a huge milestone in its new cloud-first approach as part of the overall transformation.
“We had a major accomplishment back in November of 2018 where we literally shut down our last primary owned and operated data center,” Del Vecchio said.
“So we had this kind of ‘T-minus’ schedule out there. And we have some incentive to really get it done in a time frame, which I think actually helped in many ways put that kind of goalpost out there and said we have to do this by a certain date because were just no longer going to be able to operate in that environment.”
Transformation at Guardian: What Comes Next
As the data centers were mothballed, Del Vecchio’s team also continued moving what he called “a big bulk” of our applications to AWS.
And while there’s still more work to be done in that area—there always is, right?—Guardian’s now got the technology platform required to move at the speed of the market in evaluating new opportunities, creating new products and forging new partnerships within the booming InsureTech community, Del Vecchio said.
“Now we feel like we’re in a platform. And we’re capable of testing and learning a lot faster than we have in the past with much less of an investment. But we also have access to these new technologies and just as importantly, the people that are developing these new technologies.”
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