Over the past year, I’ve had the opportunity to sit down with hundreds of CIOs navigating the “messy middle” of AI, where ambition is high, expectations are rising, and the path forward is anything but clear. In those conversations, one theme continues to surface: Many organizations know what they stand for, but far fewer know how to operationalize it.
From strategy decks to earnings calls, concepts like “customer-first,” “trusted partner,” and “digital leader” show up again and again, but translating those principles into consistent, repeatable outcomes remains one of the hardest challenges in modern enterprise leadership, especially as the pace of change accelerates.
In my recent Tech Whisperers podcast conversation with MassMutual CIO Sears Merritt, we explored this issue through a different lens, grounded not in slogans but in systems. As head of enterprise technology and experience at a 175-year-old institution built on long-term trust, Merritt knows that consistency is a discipline, and it’s key to turning “customer-first” into daily decisions. Just as critical is having leaders who can pull it all together to orchestrate outcomes for each of the constituent customer groups.
After the podcast, Merritt spent some more time discussing the CIO’s role as an orchestrator and how to make sure the discipline of consistency holds, even as organizations are being asked to adapt faster than ever before. What follows is a blueprint for how a modern CIO operating as an enterprise orchestrator across technology and experience turns values into outcomes at scale.
Dan Roberts: A lot of organizations talk about being customer-first, but very few deliver it consistently over time. What are the mechanisms or disciplines you’ve put in place to ensure that principle shows up in day-to-day decisions?
Sears Merritt: There are two strategic focus areas that drive the change we need to have in place to meet those needs. First is, “Meet people where they are with the products and solutions that they need.” That implicitly says, regardless of how a policyowner wants to become a member of the company, we’re going to make sure there are experiences and solutions available to meet them where they are.
The second one is our focus on ease of doing business. We’re really focused on making sure we’re evolving the way we’re doing business to meet the needs of today and anticipate the needs of advisors and future policyowners, and we measure that through Net Promoter Score (NPS) from our customers and NPS from our advisors.
So being customer-first is part of the goals, it’s part of the thinking, and it’s part of the strategy. Then it’s up to the technologists to make sure we’re coming up with innovative ways to achieve those outcomes.
It’s one thing to define a principle, but another to operationalize it across a large organization. How do you embed that mindset into decision-making at scale, especially when teams face real trade-offs?
It’s all about setting priorities and goals. For each of those focus areas I described, there’s a set of technology initiatives and goals the organization puts in place and then spends a lot of time focusing on achieving them. We also use the goals and their priority to help drive decision-making on any given day. More often than not, we’ve got more work than we can ever hope to get done, so we rely on those goals and the outcomes they’re supposed to deliver as the way we have leaders make decisions on a real-time basis.
You’ve talked about the idea of “building for change” rather than reacting to it. How do you ensure that consistency and trust aren’t compromised in that environment, and what does it really mean to build an organization designed for change?
There’s a concept that I’ve heard from a lot of smart people that have mentored me, one of them being Roger [Crandall, MassMutual’s CEO], and that’s “go slow to go fast.” The go slow part, I would argue, is the most important step. It’s about really, actually getting clear on what those non-negotiables are. What’s the goal? What are the constraints around the problem that we’re trying to solve? Getting that clear, and then making sure the teams that need to work on achieving it are clear on it, takes a lot of time and effort, a lot of patience, and a lot of discipline.
Spending the time upfront doing that allows teams to move extremely fast. There’s a lot less going back and basically redesigning systems because you didn’t have the right spec. That’s ultimately what this comes down to: Get the spec written down upfront, spend the time getting it clear, and then let your teams go as fast as they can, building the things they’re interested in creating.
Many organizations rely on KPIs that don’t always capture the customer experience. What do you measure to ensure you’re delivering on that promise of consistency and trust? And how do you distinguish between the lagging indicators everyone sees and the leading indicators that actually drive those outcomes?
Metrics are very easy to create, but most aren’t super useful. So I’d say, measure what matters. There’s at least one book with a title that says you should do that, but it is really important. It’s equally important, though, to not let the measures stand in a vacuum. You can have lots of unintended consequences by just putting a number in front of someone and saying, without any context around the intent behind what it means, they’re going to go move that number one way or another. If you haven’t connected it to the outcome, you could get some unintended consequences. Making sure you have measurable outcomes is important, but you can’t have lots of measures and lots of outcomes that are distinct. They’ve got to go together.
As far as lagging and leading indicators, spending time upfront during that initial discovery, ideation, problem specification, or outcome specification phase of the work is super important because it helps make sure you’re identifying leading indicators that will let you know whether you’re delivering on the outcome you’re trying to achieve.
What changes have you made to your operating model or talent strategy to deliver consistency at scale and support this way of working?
We’ve got an incredibly diverse organization, and I mean diverse in the broadest of terms — skill diversity, cognitive diversity, personal diversity, gender diversity, truly all of those different angles. We’ve spent a lot of time within the technology department here at MassMutual making sure we’ve got all the different viewpoints and all the different skill sets we need so that we can combine them to get to the outcomes.
We’re not just a team of technologists. Certainly, that’s a big part of who we are, but we’ve got folks with backgrounds in law, we’ve got economists, we’ve got physicists, we’ve got mathematicians. We have all these different backgrounds, and that was all intentional and by design. Because when you’re trying to solve hard problems, more often than not it’s not one singular skill set that’s going to get you there. It’s a combination of these skill sets and expertise that help you get where you want to go.
The way you describe that makes me think of a symphony conductor bringing together the different voices and talents in harmony. As head of experience for these different constituents — your teammates, your MassMutual colleagues around the world, your advisors, your policyowners — how do you pull all the pieces together to orchestrate outcomes for each of them?
It is all about making sure you’re creating the right environment and bringing the right people into the environment and getting them focused on the outcome. It’s much less important that I know what the outcome is. It’s much more important that I create the environment where all the people we’re going to rely on can understand the outcome and define what needs to be done to get there.
Much like the symphony analogy, it entails making sure you bring the right people onto the proverbial stage and create the environment where everybody can play their instrument when it’s needed most, to create that great sound, to create amazing music. It’s the same thing in business. It’s the same thing in technology.
We do this in a lot of ways. Our strategic management forums are an intentional convening of subsets of leaders — my leadership team but then extended leadership groups as well — where we’re focused on talking about very specific types of outcomes, whether those are operational, cyber, strategic, data, AI, or others. This intentional set of forums is designed to create the environment for the right people to talk about outcomes.
And it’s important to understand that these forums didn’t just happen. It took us, collectively on the leadership team, a lot of effort to create those meetings, as well as a lot of continuous improvement and agility, where we dialed and dialed and dialed the agendas. We dialed the things we want to talk about. We refined who was showing up. And we continue to do that. It’s not as simple as putting an invite on the calendar.
Sears Merritt reminds us that the CIOs who achieve consistency at scale and put “customer-first” into practice are focused on more than just the technology or even transformation. They’re outcome orchestrators who are measuring and shaping performance with intention. For more from his leadership playbook, tune in to the Tech Whisperers.
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