Shea Gabrielleschi
VP of Relationship Development, Financial Services

At a recent session with Pennsylvania community bank executives, we posed a simple but powerful question: How confident are you in your bank’s ability to turn IT investments into business outcomes? Only 12% said they were “very confident.”

Banks have never spent more on technology, but most are still left unsatisfied and frustrated at the end of the day. Nine times out of ten, this isn’t a tech problem but a leadership and alignment problem.

The Missing Link
One bank we worked with had accumulated significant tech debt despite investing in several best-in-class platforms. The frustration wasn’t due to the tools themselves, but rather a lack of alignment between technology decisions and business needs.

The CEO explained, “We bought a Ferrari when we really needed a Ford Explorer, and now, we’re stuck maintaining something we can’t fully use.”

The issue was that these tech applications weren’t a good fit, and the departments these solutions were designed for were left out of the selection process.

During our session, 56% said they were only somewhat confident in seeing outcomes from IT investments. And at the end of the day, this is a people problem, not a technology problem.

The bank’s business objectives are usually separated from the IT department’s project list, but IT can’t just support the business anymore. It has to help drive it.

Bring the Right Leader to the Table
Technology has quickly become so complex that having a strategic IT leader is now a necessity for most banks. But when your IT leader doesn’t understand banking, you can’t expect them to build a coherent IT strategic plan, properly prioritize IT initiatives or focus on outcomes and not just operations. Many banks have never defined what a good IT leader should do. So they end up with someone who’s great at solving problems but never asked to drive outcomes.

Shifting the Questions
If you want your IT to be tactical, ask them tactical questions. But if you start asking questions like, “How will this help us operate more efficiently?” you’ll begin to see the bigger picture and discover how strategic your IT leadership is.

Evaluate if your questions create accountability and alignment because in the end, you can spend a lot on IT and still fall behind if leadership, alignment and accountability aren’t all there.

What if IT Leader Isn’t Strategic Enough?
You may have a capable IT manager who works hard, responds quickly to issues that pop up and knows the intricacies of your core. But if they can’t translate technology into business impact, they’re not the kind of leader your bank needs right now. Banks should be wary of conflating technical talent with strategic leadership.

Many banks promote their best technician into a chief information officer role and expect them to lead at the executive level. But running IT infrastructure well doesn’t mean they’re prepared to shape business strategy. Strategic IT leadership requires someone who understands your operating model, sees around corners and prioritizes technology investments based on real business outcomes.

The Right Kind of IT Leader Is Hard to Find and Retain
The intersection of banking and tech strategy is a narrow lane, and the talent pool is thin. Even when you hire the right person, they often grow stale over time working within the four walls of one institution. That’s why more banks are turning to outsourced IT leadership, not as a stopgap but as a deliberate strategy. Done right, this model brings in fresh thinking, cross-industry insight and executive-level guidance without adding a full-time executive headcount.

But whether your IT leader is internal or external, they need to be more than a project manager. You should expect a clear technology roadmap tied to your business strategy, not just a list of upgrades. You should evaluate IT based on whether it’s helping you grow, reduce risk and improve efficiency, not just whether systems are up and tickets are resolved. And you should expect your CIO, in whatever form they take, to challenge assumptions and push the organization forward, not just keep it running.

If technology feels like it’s underperforming at your bank, the issue usually isn’t the tools. It’s the leadership behind them. In a world where your revenue, efficiency, and customer expectations are all under pressure, you can’t afford to leave IT stuck in a reactive, tactical box.

WRITTEN BY

Shea Gabrielleschi

VP of Relationship Development, Financial Services

Shea Gabrielleschi is the VP of relationship development at Hartman Executive Advisors. He works at the intersection of banking, technology, and growth strategy, helping community banks turn IT from a cost center into a competitive edge. He’s passionate about empowering bank executives to make technology a driver of growth, efficiency, and long-term performance. Mr. Gabrielleschi began his career with the Independent Community Bankers of America and has spent more than a decade embedded in the banking ecosystem as a connector, advisor, and advocate. At Hartman Executive Advisors, he leads growth across the financial services practice, working closely with bank leaders, fintech partners, and industry associations to help institutions stay competitive and future-ready.