Finding the Right Tech Leader: MidWestOne’s CIO Search

When Chip Reeves took the helm as CEO of MidWestOne Bank, Iowa City, Iowa, in late 2022, he saw an institution with deep community banking roots but a growing need for modernization. With a footprint stretching across Iowa, Minnesota, Wisconsin, and Colorado, the bank had rapidly expanded from $1.5 billion to $6.5 billion in assets. Yet, as Reeves evaluated the organization, he recognized that while the bank had scaled in size, its technology infrastructure and internal processes had lagged. 

“We embarked on an evolution—a transformation of the organization,” Reeves explains. “MidWestOne has a great core deposit franchise, and it’s the bedrock of our organization. But we had to ask ourselves: Who are we? Who do we aspire to be? Where can we win in this new framework where technology plays such a huge role?” 

To answer these questions, Reeves knew MidWestOne needed a technology leader who could align the bank’s IT strategy with its long-term vision. That realization led him to a national search, ultimately bringing in Paul Ho-Sing-Loy as the bank’s new Chief Information Officer. 

The Need for Strategic Tech Leadership in Banking

The challenge Reeves faced was clear: MidWestOne needed a CIO who could bridge the gap between tradition and transformation. It wasn’t just about hiring someone with technical expertise—it was about finding a leader who could synthesize complexity, articulate strategy, and implement change at a pace that matched the bank’s ambitious growth trajectory. 

“As executive teams, we tend to have functional expertise in areas we grew up in,” Reeves notes. “There aren’t many CEOs who came up through the technology side of banking. I certainly didn’t. And when it came to recruiting the right leader for this role, our internal networks simply weren’t broad enough to find the caliber of person we needed.” 

Recognizing the need for external expertise, MidWestOne partnered with Patrick Cooney and Brian Love from Travillian, the King of Prussia, Pa., executive search firm dedicated to placing senior-level professionals in the financial services industry. 

Paul Ho-Sing-Loy: A CIO with Diverse Banking Experience

Paul Ho-Sing-Loy wasn’t looking for just any opportunity—he was looking for the right fit. With a career that had taken him from major financial institutions ranging from Citibank and Wells Fargo to regional banks like Lakeland Bank in New Jersey, Ho-Sing-Loy had experience scaling technology operations for institutions in the $5–10 billion range. 

“I’ve been at big banks, small banks, and credit unions,” Ho-Sing-Loy says. “The problems in traditional banking are largely the same: managing third-party dependencies, integrating legacy systems, and ensuring that technology is leveraged to improve business outcomes. The question is always: How do we get better?” 

When MidWestOne explained its need, he saw an opportunity to apply his expertise in a setting that valued strategic alignment as much as technological advancement. 

“I really liked how I felt I could fit into this team,” he recalled. “[CEO Chip Reeves] has done a great job making sure everyone is on the same page. The culture was a great match for me, and I knew I could make a difference.” 

Identifying Bank Tech Priorities

Stepping into the CIO role, Ho-Sing-Loy wasted no time in assessing the bank’s technology landscape and identifying key areas for improvement. 

“My first priority was understanding what we do well and where we need to improve,” he says. “That meant evaluating our skill sets, identifying gaps, and ensuring we had the right people in place. It also meant looking at our external partnerships—who we rely on and how we can maximize those relationships.” 

The bank was also facing the broader industry challenges of digital transformation. 

“As banks grow, they need different kinds of people with different skill sets,” Ho-Sing-Loy explains. “We also need to manage third-party dependencies carefully. Community banks work with providers like Fiserv and FIS, but we have to ensure we’re not overly reliant on them. And of course, AI is a game-changer. If you’re not leveraging it, you’re already falling behind.” 

Bank CIO’s Strategic Tech Roadmap

Seven months into his tenure, Ho-Sing-Loy has already had significant impact. The bank has: 

• Expanded its DevOps team 
• Hired in-house coders for the first time 
• Greenlit major technology initiatives, including: 
  • A new ServiceNow implementation for back-office operations 
  • A revamped online banking platform set to launch this year for commercial banking and in 2026 for consumers. 

Reeves has been impressed with the rapid progress. 

“Paul has been an absolute game-changer,” he says. “From day one, he has synthesized complexity and laid out a clear roadmap that aligns our technology investments with our strategic plan. That’s exactly what we needed.” 

The Importance of Strategic Investment in Banking Technology

Reeves and Ho-Sing-Loy both emphasize that any bank undergoing a technology transformation must be prepared to invest in the right people and ensure organizational alignment. 

“The biggest mistake banks make is underestimating the investment needed—not just in technology but in leadership,” Reeves says. “Hiring a CIO isn’t just about plugging a gap; it’s about positioning the bank for the future.” 

Ho-Sing-Loy echoes that sentiment. “You can’t take the easy road,” he advises. “The challenges we face today are only going to get more complex. The key is having the right people in place, the right strategy, and the willingness to evolve.” 

The complete interview that served as the source of this article—conducted by Travillian’s Brian Love, Head of Banking and Fintech, and Patrick Cooney, Banking and Fintech-focused Recruiter—can be found at Travillian Next.