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Country Bank selects CTO to bolster IT capabilities

By CIO Dive by By CIO Dive
March 13, 2026
Home Enterprise IT
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Dive Brief: 

  • Country Bank appointed Ryan Stepalavich as SVP and CTO to lead the firm’s technology strategy and improve efficiency and innovation for customers and employees, according to a Thursday announcement. 
  • Before joining the Massachusetts-based bank, Stepalavich held IT leadership positions at Savings Institute Bank & Trust and Berkshire Bank where he led efficiency initiatives and IT infrastructure modernization. Stepalavich brings more than 26 years of IT experience — including 14 years in financial services technology — to his role as CTO at Country Bank. 
  • “I look forward to working with the team to ensure our technology continues to support innovation, strengthen security, and enhance the experience for both our customers and team members,” Stepalavich said in the announcement. 

Dive Insight: 

Banks are modernizing systems to trim costs, improve operational efficiency and create better experiences for customers. 

Legacy IT systems are causing banks to lose customers, a Baringa survey found. Outdated technology negatively affected customers’ online experiences, 68% of surveyed executives said. 

Challenges posed by legacy IT and the evolution of AI tools in banking are placing technology leaders at the forefront in leading new digital initiatives. During Stepalavich’s tenure at Berkshire Bank — now Beacon Bank — as VP and principal solutions architect and engineer between 2023 and 2025, he led IT guidance and performed IT project management functions for more than 60 bank initiatives, according to his LinkedIn profile.

Among those initiatives, Stepalavich converted Skype for Business Server to Microsoft Teams, “enhancing connectivity, collaboration and voice functionality for 1,400 users.” He also deployed publisher infrastructure for Netskope Zero Trust Network Access, “securing and simplifying remote access for 800 users.”  

Stepalavich also helped plan, design and execute the systems merger of Savings Institute Bank & Trust and Berkshire Bank, after a 2019 acquisition. 

Earlier this year, Marco Bernasconi, first SVP and chief operating and innovation officer at Country Bank, said growing the firm’s technology capabilities in a sustainable manner requires intelligence, efficiency and automation. 

In the Thursday announcement, he said he anticipates that Stepalavich’s prior experience will contribute to continued innovation and growth at Country Bank. 

“His extensive experience in financial technology and collaborative leadership approach will help us continue to strengthen our technology capabilities while supporting the innovative and customer-focused banking experience our communities expect,” Bernasconi said.



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By CIO Dive

By CIO Dive

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