Ryan Stepalavich

SVP, Chief Technology Officer at Country Bank

Greater Boston, United States

About Ryan Stepalavich

Ryan Stepalavich is SVP, Chief Technology Officer at Country Bank. Location: Greater Boston, United States.

I’m a financial‑sector technology leader with 20+ years of experience modernizing infrastructure, strengthening cybersecurity, and improving operational maturity across community and regional banks. I specialize in building stable, well‑governed, cost‑efficient environments that support business growth and regulatory expectations. I lead with a communication‑first approach - maintaining strong alignment with business lines, visiting branches regularly, and ensuring technology strategy reflects real operational needs and frontline experience. My focus is bridging the gap between technical execution, executive strategy, and regulatory compliance - turning complex IT, risk, and cloud requirements into clear business decisions. Across my career, I’ve delivered modernization initiatives spanning infrastructure, cybersecurity, identity, cloud, data transformation, and enterprise collaboration. I’ve authored executive‑level strategic plans, governance models, and ROI analyses that help leadership make informed, long‑term technology decisions. I’m currently exploring senior technology leadership roles - CTO, VP of IT, Director of IT, or Enterprise Architect - where I can continue driving modernization, operational stability, and strategic alignment in mission‑driven organizations.

Skills

  • Enterprise Architecture
  • Information Technology Infrastructure
  • Technology Management

Additional experience

  • Vice President, Principal Solutions Architect & Engineer

    Berkshire Bank

    April 2023 – December 2025

Education

  • BA, Eastern Connecticut State University
  • Management Information Systems, University of Connecticut