Tech transformation

Throughout his 30 years, Bradley Enneking has tended to question the status quo.

“Why are we doing things the way we are? Why does this process work like this?” he would ask, inevitably setting off a process that would lead to finding shortcuts and efficiencies that were previously invisible.

“One of the most impactful skills I developed was being curious about how things worked and why things worked the way they did,” he tells The CEO Magazine. “I can look back at three or four of the career advancements that I got, and it was largely because I was just a pain.”

Enneking’s curiosity, coupled with his natural affinity for technology, has been key to his success at HTLF Bank – a US$20 billion bank where he served as Chief Information Officer (CIO) from 2020.

“Ever since I was very young, I was really enamored with technology. No matter where I started, I felt like I would’ve ended up in technology because it was just something I was always drawn to,” he says.

After obtaining a degree in computer engineering in the 1990s, he spent years working in tech and consulting before joining Wells Fargo in 2011. He stayed there for nearly a decade, initially working in customer-facing roles before transitioning into operations and sales and ultimately managing the company’s online and digital properties.

After Wells Fargo came under regulatory scrutiny during a fraud scandal in 2018, the company sold off its asset management business, where Enneking worked at the time. Fortunately, a former colleague recruited him to join HTLF and lead its digital transformation.

A carefully planned expansion

Enneking sees himself as part of a new breed of CIO that is more involved in key business decisions than CIOs have been in the past.

“CIOs really need to be much more of a partner at the table talking about organizational strategy,” he says.

“For the last 10 years, there’s almost nothing you do in your organization that doesn’t rely on technology. You start every workday by opening your laptop. There’s a lot that goes into making that work seamlessly.”

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The CIO decides which technologies an organization uses and how those technologies need to be used to support the business without putting sensitive data about staff, customers or the organization at risk. Even popular digital tools like Salesforce, Infoverity and ServiceNow require planning and training to make sure they are used safely and efficiently.

Enneking inherited these responsibilities at a time when HTLF was expanding through a series of acquisitions of nearly a dozen other community banks. For over a year, he and his team devised careful plans for each new business to enter the HTLF fold, along with all of their data and digital processes.

“Our biggest single operational challenge was aligning over 60 vendors to deliver a complimentary function at the same time, literally on the same day,” he recalls. “We had to do that 11 different times, which required constant support and monitoring.”

In addition to aligning all 11 brands around the same technological tools, HTLF also had to make sure they all followed uniform processes for setting interest rates, engaging with customers and executing loans.

“There were hundreds of different processes that were in place, and people were used to doing things the way they did for the last 20-plus years, so it was tough to come up against that momentum,” he says.

The experience taught Enneking some key lessons about acquisitions.

“The acquirer has the responsibility to communicate, be transparent and really share their culture as much as possible,” he says. “Then the folks at the organization being acquired really have the choice about whether to engage in that culture or not.”

The next chapter

Enneking is now faced with an opportunity to put that lesson into practice. As of early 2025, HTLF was in the process of transitioning into a branch of UMB Bank following an acquisition. He hopes to steward that transition in a consultative role before sharing his expertise elsewhere.

“My sweet spot is where an organization really needs some sort of digital transformation or wants to expand quickly,” he says. “Anything involving significant organizational impact and change is an area where I have done a lot of work through my career and is an area that really excites me.

“I’m in a position to be able to give back and provide some guidance and talk about some of my experience in a startup setting and also leverage my network to help somebody grow.”