‘Boomerang’ CIOs: IT leaders level up by coming back

IT execs are capitalizing on return journeys to former employers, bringing newfound leadership insights to familiar business issues. Returning IT leaders discuss why they did it and what they’ve gained.

When Matt Postulka left Arbella Insurance Group as deputy CIO at the start of the COVID-19 pandemic, he didn’t intend to look back. Postulka aspired to become a CIO — and he achieved it, landing a job as CIO and senior vice president of technology and operations at the Federal Reserve Bank of Boston.

It made sense to leave Arbella because “there was a great leader in place” and “I was feeling that CIO was several years away,” Postulka explains. He was interested in “doing something a little different,” and leading technology at a quasi-governmental entity where he would be responsible for two business areas held great appeal. “So there was an interesting opportunity to get my hands dirty running a business operation.”

But in 2022, after two years at the bank, Postulka returned to Arbella as vice president and CIO.

Postulka is an example of a boomerang IT leader — professionals who leave a company, gain experience elsewhere, and then return in a higher tech leadership position.

These boomerang CIOs have every reason to be as successful as a more traditional external new hire, but not more so, according to Martha Heller, CEO of Heller Search Associates. “Technology moves so quickly, and cultures are going through so much transformation, that the company the IT director left is likely to be very different today,” Heller says. “Previous relationships can help a boomerang leader get quickly up to speed, but unchecked assumptions about the culture can be a derailer.”

Gaining a fresh perspective

Kevin Miller worked as a technical solutions architect at enterprise software provider IFS Americas for about two years before leaving to become director of global pre-sales solution architects at software provider Loftware in 2020.

IFS was in a transition period under new ownership and had received private equity funding and a new president, so the culture was changing, Miller recalls. “That was great, and I was 100% on board, but I felt I was in a role that could potentially not change, and I felt I wasn’t growing,” he says. Moving to Loftware “was an opportunity to go retool this other team.”

Kevin Miller, CTO of the Americas, IFS

IFS

A little over a year later, however, Miller returned to IFS as an associate vice president and is now CTO of the Americas. “The most important thing to me was I gained a fresh perspective on something different,” he says, referring to his job at Loftware. “It was a company that was also developing enterprise software but was much smaller,” and took a different approach to leadership.

During his time at Loftware, Miller learned how to deal with and lead teams in different cultures and time zones, and because it was at the height of the pandemic, “I learned a lot of remote leadership skills, and that became invaluable,” he says.

His former manager, who was CTO of the Americas at the time, was planning his retirement and reached out to Miller. “I was gone maybe 60 days and he called me and said he missed a leadership opportunity with me,” Miller recalls. “Quite frankly, we had conversations for months on how to retool teams and what role I would be [as] successor to him.”

Then the discussions stalled, and Miller grew skeptical, but eventually, IFS’ president of the Americas formalized his return.

During his first stint at IFS, Miller “had a lot of creative ideas, but they were mostly met with ‘We do these things because we’ve always done them that way,’ which I think is one of the worst things to say.”

Before Miller returned, IFS’ president made it very clear that Miller’s ideas would be heard, and “that’s what solidified it for me,” he says. “I wanted to come back to effect change and was excited and on board about how I could come back and inject my skillsets into the team.”

They worked through a transition plan, and six months after he returned, the CTO retired and Miller was promoted.

While he was at Loftware, Miller says he was exposed to different methodologies and technologies for demonstrating their software product. “Even though that organization was much smaller … they were able to achieve things we [at IFS] struggled with, so there were a number of initiatives we put in place upon my return.”

Miller’s goal was to foster an environment of being nimbler and giving software teams greater autonomy. He says he made it clear that he was there “to empower them and support them to do their best work, rather than the traditional top-down approach of ‘Hey team, here’s what you need to do.’”

His time away made Miller better suited for the CTO role because it gave him “exposure to other diverse situations,” he says, and different customers, which led him to develop “creative approaches” to problem-solving.

Familiar culture and people

While at the Federal Reserve Bank, Postulka learned a lot about cybersecurity and infrastructure, which he says complemented skills he had in app development and software engineering.

Moving into the C-suite, especially during the pandemic, Postulka discovered what it took to be an executive and lead a remote team through videoconferencing. That meant having to effectively communicate and influence people all around the country, he says.

Matt Postulka, CIO and VP of IT, Arbella Insurance Group

Arbella Insurance Group

When the CIO role opened up at Arbella, Postulka’s interest was piqued. To fulfill his career goals at a company he was familiar with was an intriguing idea, but “honestly, what brought me back was the culture and people,” he says. “Arbella is a great place to work, and I had stayed in touch with so many of folks I had worked with over the years at a company I was very proud to work at.”

Postulka credits both organizations with teaching him the importance of building connections and relationships by being patient and listening to what people have to say. When you have an idea that you want support on, you might get pushback, he says, but that’s where negotiation comes in.

Becoming a successful CIO requires learning “where to stand your ground and when to be less selfish and more selfless. … It helps get you support at the executive level,” Postulka says. “It also doesn’t hurt to have allies on the executive board and you have to realize you can’t do that all alone.”

The most important leadership principles he has learned from his journey leaving and returning to Arbella? The importance of surrounding yourself with the right team and how vital it is to retain talent. “Everyone says that,” Postulka notes, “but it’s so critical to your success and the organization’s success.”

How best to boomerang

Both Postulka and Miller say that if you’re considering returning to a higher-level IT position at a former company, first consider what you’re trying to achieve in your career.

Situations at former organizations change, and several years can go by, “but if you’re still familiar with the culture and there are consistent threads, and if that appealed to you in the past, strongly consider whether it will be an enabler for you going forward,” Postulka says.

For some, returning to a previous employee may feel like going backward, even when leveling up. But for Postulka that has not been the case. Instead, it’s been an opportunity to shape and build something for himself and for an organization he continues to care for.

“I gained a ton of experience for two years [at the Federal Reserve Bank] and have a broader perspective on how things can be done, and I’m applying that to an organization I’m familiar with,” Postulka says.

Miller agrees, saying he felt he had unfinished work to do at IFS. “It has felt like home since I’ve come back … I feel like I am where I belong.”

He adds, “You have to do it on your terms and how it fits in with your personal growth and the career story of what you want to accomplish.”

SUBSCRIBE TO OUR NEWSLETTER