CIO Mavericks: Introducing Brad Hildestad, CIO at COUNTRY Financial

The “disruptive CIO” is becoming a popular phrase to describe a new brand of IT leader that introduces radical new approaches and challenges the status quo. At Solstice, we believe in challenging conventional wisdom and honoring the opinions of industry leaders who dare to think differently: the mavericks.

That’s what Solstice’s CIO Mavericks series is all about — asking demanding questions and discovering what motivates and inspires the boldest IT executives.

Our guest for this installment is Brad Hildestad, Senior Vice President and CIO at COUNTRY Financial, a U.S. based financial services company offering a wide range of insurance and financial products and services. Brad joined COUNTRY in 2015, bringing deep expertise and experience in IT infrastructure management and support. In his current role, he is responsible for providing overall strategic direction for the company’s technology and information functions. This includes incorporating emerging technologies that support corporate strategies with an emphasis on mobility, security and improved client experience. 

During our in-person interview, Brad shared his insights across a broad range of topics including digital trends and strategy, technology modernization, organizational alignment and IT security.

Mike Koleno: Thanks for taking the time to chat with us. I know you have been at COUNTRY for about four years and have extensive IT management and support experience within the insurance sector. Can you give us a little more insight into your background and your career and how you arrived in your current role?

Brad Hildestad: Prior to joining COUNTRY in 2015, I had spent 29 years in the insurance industry working across all areas of IT. Most of the time I was managing infrastructure and operations, but I also spent a fair amount of time in applications as well. When I came across this opportunity at COUNTRY, it appeared to be a good fit. The company’s community-based culture and long heritage of providing protection and providing financial security, really stood out to me ― it is very people-centric and welcoming. The company is also over 90 years old, well-capitalized and firmly established.

One thing I did look closely at was the company’s IT organization and where it was in its maturity journey and its expansion in the digital space. I liked what I saw and felt I could add substantial value to the role and make a significant impact to the IT organization. My instincts were correct — that’s precisely how things have worked out thus far. While we've made great progress, there's always plenty left to do.

 

"With technology and the insurance sector constantly changing, you never know where the next disruption will occur and how best to respond — and that’s what is most exciting."

 

MK: What I think is interesting about COUNTRY IT is that it is highly centralized — you've got multiple stakeholders that you are working with. Can you talk about that in terms of how you work with your peers to collaborate and prioritize across a diverse set of lines of business and products?

BH: Absolutely. When I joined COUNTRY, it had already transitioned into more of a centralized, shared IT service structure, with a couple of exceptions. One outlier that remained outside our scope of responsibility was the digital engagement and customer experience function, which is aligned with the marketing organization. The structure is a little different from what I'd seen in the past, but it seems to be more where the industry is going.

What we’ve done with the business units is strengthen the relationships with IT. In our current structure, we have a vice president overseeing applications and then each business unit has what I call a 'mini business unit CIO.' As director of application development, they own that relationship with the business unit. They own the portfolio. They plan how and where they want to go with their technology and then they work together on the project strategy and execution.

Another change we made was moving into an Agile development model, which has helped to further strengthen our relationships and increase the interaction between the IT organization and the business units. The centralized approach has worked well, helping to ensure each business unit gets the attention and focus it needs.

 

"I don't anticipate any near-term changes, but we continue to evaluate processes, and if there's an opportunity to make improvements, we make them." 

 

MK: It looks like this hybrid approach gives you the best of both worlds. I like direct ownership from a line of business standpoint.

BH: You're right — it is sort of a “hybrid approach” and is one thing we are doing uniquely. We've also done some exceptional things with our data and analytics resources, extending them out into the business units, which has helped to further strengthen the relationships with IT.

It works well, but at the same time we need to have some element of governance. As an organization we recognize that, and we're all committed to doing the right things. We'll continue to fine-tune our progress in these areas.

MK: You mentioned digital. I know roles and responsibilities continue to shift in this regard, but can you talk a little about what the future looks like as it relates to digital in terms of your responsibilities for digital outcomes?

BH: We recently completed a restructuring where we added a chief experience officer. This position is responsible for all the business units that are directly customer-facing — that includes claims, customer service, billing and marketing — so certainly this role will be a strong partner with IT in our digital journey. 

However, at COUNTRY, the heart of 'digital' discussions is really about making it as easy as possible for clients to do business with us in whatever way they choose.

 

"So 'digital' isn’t one team or one channel – it’s really everyone working together to do what’s right for our clients.

 

We’re also in the process of implementing a new claims system within the claims organization. We're doing that with a systems integrator and tight partnership between us and the business. That is going well. While it’s still early, I don't anticipate significant adjustments for now.

MK: That's great. One key objective that I know you've been pushing forward over the last couple of years is a strategic modernization of your backend systems. I’m keenly aware of the challenges involved with those efforts as well. You can't just snap your fingers, and everything is modernized overnight. Can you talk about that journey?

BH: Like most insurance companies that have been around for a while we have a lot of legacy systems. We’ve been on a modernization journey for some time and have made great progress, but at different rates and on different scales. Some of the efforts are quite large and take multiple years and substantial investment — like replacing the policy admin system, claim system or installing a CRM platform. Other efforts we’ve modernized are more straightforward. We’ve added new data centers in a co-location approach and were able to do that within a couple of years. We've also refreshed our security infrastructure within the data center. While we've made great progress in many areas, other areas are taking a little bit longer.

Indeed, that is one of the biggest challenges — that you can't do it all at once. You need to be patient and have discipline in your execution. The good news is that with our strong alignment between business and IT, we’re able to gain alignment to invest in the future and do an excellent job at lifecycle management. 

MK: You also mentioned security. We know that security continues to be a top concern for CIOs. With substantial legacy technology and complex infrastructure and mission-critical systems, data security presents a difficult challenge. Can you talk through your approach and perhaps share some of the practices you’ve employed to bolster your security readiness?

BH: First, it starts with corporate and enterprise commitment. Certainly, we have that. One of the things that I've been doing since I've been here is really working to build a strong security team. I value diversity. So, as I've been building my team, I've been building a diverse team in all aspects — from location, industry, experience, and technology — and I do that with all of my teams. While we have been maturing our security practices and leveraging traditional best practices, I’ve also been bringing in expertise from the outside with new ideas.  People play a vital role, so I’ve been encouraging our team to continue to grow and learn.

As part of our ongoing maturity assessments, we've refreshed a lot of legacy security infrastructure with newer technology that meet the needs of the changing security landscape. We have a three-year plan that defines how and where we want to grow our security technology.

 

"At COUNTRY, we're all about the financial security of our clients and underpinning their financial security is the security of their data and information — we are very committed to that.

 

MK: You mentioned the shift to Agile. I think there's a wide spectrum of maturity as it relates to many organizations. Can you talk about that transformation as well?

BH: I honestly like where we're at. About four years ago when I joined, we weren't really doing any Agile development. But we know it's key to our success in the future. We must have speed to market, and we need to be flexible in our designs. So, we came up with an Agile program and over the last four years we've been rolling it out throughout the organization. We're doing about 60% of our development work right now with Agile.

We're still learning, and it takes commitment and support from the business units. We have that, but it means that everyone has to change how we think and how we do work. It’s a challenge when you've been doing something the same way for many years.

MK: As organizations increasingly look to CIOs as the agents of change, can you give advice to CIOs in this regard, particularly those who maybe don't have a list of digital initiatives or strategic efforts at the ready?

BH: As you might imagine, when I joined COUNTRY, there was a lot of ingrained culture and established practices. First, my advice would be to simply embrace the culture and recognize that it has strengths that can be leveraged. You have to be really involved and be the leader of change. You have to bring technology leaders and teams along and stay engaged. For example, I meet with our leaders every week for at least an hour, this is something different and new. This element of change is difficult to explain and for many, the value of change is hard to understand. 

In a larger sense it’s about embracing that change because the status quo is not an option. Our industry is not sitting still. Technology's not sitting still. 

 

"Some business units will embrace change faster than others. You have to be aware of that and know when you may be moving too fast or pushing too hard.

 

MK: I love that, particularly your point about spending time with frontline leaders for hours and your commitment at the CIO level. 

BH: In fact, just before our conversation here, I had what I call my CIO round tables. I spend an hour once a month with a group of 15 to 20 employees. We just talk about what's going on. And it's interesting — the conversations four years ago are so different than the conversations today. Clear communication and honest feedback can take you a long way.

I'm a firm believer that the way you succeed in IT is with your people and your workforce. We know that supply and demand doesn’t always balance out, so it's really important that we build an environment where people feel encouraged to join and motivated to stay.

Follow Brad on LinkedIn.