Monica Caldas is an award-winning digital executive who leads a team of 5,000 technologists as the global CIO for Liberty Mutual Insurance. Caldas has established herself as a decisive, growth-oriented executive and innovative strategist with an impressive track record of leading large complex transformations and executing with real solutions.
Caldas joined me for a recent episode of the Tech Whisperers podcast, where she opened up her leadership playbook and discussed what it takes to be a truly innovative, tech-forward company, one that leverages technology to gain first-mover advantage.
After the show, we spent some more time focusing on the work Caldas and her organization are doing to build a digital-savvy workforce and further differentiate Liberty Mutual on the global and local levels. What follows is that conversation, edited for length and clarity.
Dan Roberts: Can you provide some context around how you think about IT’s role in helping the business compete and ‘put points on the board,’ as you say?
Monica Caldas: I always think of technology as having a defensive and an offensive side. As a technology organization supporting a global insurance company, job No. 1 is enabling secure, stable systems. That’s the defensive side. We operate a large ecosystem around the globe with many jurisdictions, so making sure our systems are up and running for our customers, employees, and brokers 365/24/7 is critical. We must deliver on our promises at all times. In addition, we have to have the right people with the right skills focused and aligned to the right problem statement, and I’m proud of the team we have built.
On the offensive side, it’s about deploying new capabilities and features that help us differentiate ourselves. Right now, we are thinking about, how do we leverage artificial intelligence more broadly? We’re not at step one of that journey because, as an insurance company, we have been leveraging AI for many years, but we are thinking about generative AI in the sense of, how do we empower our employees and augment their work to help them have more capacity and for higher, more complex work sets?
So, for us, it’s always offense and defense, in tandem. We’re modernizing our ecosystem. We are continuously deploying new data capabilities and insights, we are pushing forward with our digital progression agenda, and we’re also building these generative AI capabilities internally to help our employees have more productivity in their day to day.
Jim MacPhee, a business and tech partner of yours for many years, says he’s always inspired by your curiosity and how you focus on getting a deep understanding of the critical business outcomes you’re driving to accomplish for your customers. What motivates that high level of curiosity?
I have a philosophy that we have to solve business problems. In order to solve them, my technology team and I have to understand them at a deeper level.
I often say, whatever problem you’re solving, ensure you have the full context. Many times it means going and seeing for yourself. For example, I was trying to understand underwriting in our Canadian operations. I flew to Canada, and I sat with the underwriters to understand why this capability we deployed wasn’t being used. The underwriting community was saying, ‘Well, it’s hard to use. It’s sometimes slow.’ And in technology, you can easily jump to, ‘Okay, let me solve for latency. Let me solve for user experience.’ In that example, it was better to just go and understand what is happening locally.
We operate from a philosophy that we need to solve real problems and not just create outputs but create outcomes. One of the ways you can do that is to go and see and have a shared context and get alignment on what real success looks like
Your team is doing amazing work in the data space. What’s your mindset when it comes to data? How are you harnessing it for competitive advantage?
As leaders in the technology landscape, it is imperative that we recognize data is a shared asset, essential to every function within our organization. Whether you’re in claims, finance, or technology, data literacy is a cornerstone of our collective accountability. To this end, we’ve instituted an executive education program, complemented by extensive training initiatives organization-wide, to deepen our understanding of data.
By demystifying data and going beyond its abstract nature, we empower ourselves to harness it effectively. This commitment ensures that every team member becomes a responsible steward of the data we access, ultimately driving innovation and excellence. We are still maturing in this capability, but we have fully recognized that we have shared data responsibilities.
Our approach is two-pronged. We have a data office that focuses on data governance, data domain stewardship, and access, and this group sits outside of IT. It’s federated, so they sit in the different business units and come together as a data community to harness our full enterprise capabilities. On the technology side, we think about the engineering aspects — access, platforms, tools, insights, transformations, all these different components to it.
We bring those two together in executive data councils, at the individual business unit level, and at the enterprise level. We have matured our data literacy, which has led to different conversations today than we had maybe five years ago. Today, we look at the maturity level needed across the domain and what data sets we need for what problem statements, and then bring that sense of stewardship forward to each of the data offices.
I also believe that, in everything we do, data is the fundamental piece that will enable us to be successful, and so we must understand what data sets are the most critical to what decisions. If we understand the data better and derive better insights, it enables us to offer better products and services at greater speed.
So that’s the journey we’re on. We have modernized most of our data warehouses, we have put in new tools and capabilities, and that’s great, because now we’re at this next inflection point of technology with gen AI. So it’s very timely.
Everyone talks about being a tech company but few are as intentional as you are in raising the digital acumen across the company. What are you doing to build a more digital-savvy workforce?
We are dedicating tremendous energy to ensure our skills are not only robust for today but also poised for tomorrow. I’m focused on leveraging the digital IQ of every employee, amplifying the impact of our 5,000 hands-on technologists.
Several years ago, we launched Executech, a program designed to equip business leaders with a deep understanding of technology fundamentals. It covers essential topics like artificial intelligence, our use of data models, our approach to technical debt, and the modernization of legacy systems. We explore the essence of data and the intricacies of data engineering. Our goal is to make technology dialogue approachable to accelerate our ability to drive impact with technology.
Speed is so important in the time we’re operating in, and by having cross-functional tech savviness, it creates collaborative problem solving across the company. These are the conversations that will set the company up for the future.
You were early (and right) with big bets on generative AI — one of those major ‘answer the call moments’ that every CIO faces. How has that unfolded, and where are you in that process?
Our portfolio of AI capabilities is ever-evolving, with generative AI being a key focus area we’re actively exploring and deploying for internal use. Using a defensive and offensive strategy, we’ve taken decisive steps to ensure responsible innovation.
On the defensive front, we established a Responsible AI Steering Committee. This team addresses potential risks, manages AI across the company, provides guidance, implements necessary training, and keeps abreast of emerging regulatory changes.
Simultaneously, on the offensive side, we’ve launched our internal Liberty GPT instance. This initiative offers a safe environment for learning and experimentation. I envision all 45,000 employees engaging with Liberty GPT after their training, fostering an intuitive understanding of AI’s potential — to explore and learn.
We’ve structured our approach into phases. Phase one involved organizing, establishing the foundational framework, convening the Responsible AI Steering Committee, understanding model limitations, building third-party partnerships, and setting up our internal instance while assessing our tech architecture. Phase two focused on developing use cases, creating a backlog, exploring domains for resource allocation, and identifying the right subject matter experts for testing and experimentation.
Fast-forward to today, about 18 months into our journey, and we’re at phase three. We have 25% of our employees on Liberty GPT. We have a backlog of over 200 use cases that we’ve prioritized, 10 of which we have in production. They’re all-around specific capabilities — a summarization capability or a question-and-answer capability — so that we don’t duplicate efforts across the company. We’re doing use cases that help our employees be more productive in their day to day.
We are also testing it with engineering. I like to say that we need to drink our own champagne, so it’s about how we are thinking about it within technology and how we can use it to think about what processes we use today that should be more machine-led and less human-led. We have been deploying some tests and experimenting and thinking about, how do we make engineering a better experience and enable us to work on more complicated parts of the engineering lifecycle?
I think we’re very much on our way. For us, the next frontier is going to be the reference architecture and how do we leverage large language models versus small language models, and how do we think about transformation of processes, not just use cases and points in time. We’re on the right path, and we will not sit on our hands to wait and see.
It’s clear that Caldas’s ability to execute on her vision has put the company on the right path and has set it up for even bigger things down the road. For more valuable insights from her digital leadership playbook, tune in to the Tech Whisperers podcast.
