Chesapeake Bank -

We’re not looking for a tech magician—we’re looking for a strategic partner who knows how to build on what works and make it better. We’re looking for a CIO who is a visionary technology leader ready to shape the future of our enterprise IT, business applications, and project management efforts. You’ll work closely with senior leadership to ensure our systems support the business—not the other way around.

What You’ll Be Doing

• Strengthening and scaling enterprise applications and infrastructure
• Aligning technology initiatives with business strategy
• Managing vendor relationships and optimizing service delivery
• Supporting data governance, compliance, and security

What You Bring

• Proven experience in enterprise IT leadership
• A practical mindset with a focus on scalable solutions
• Strong communication and team-building skills
• Comfort working within established frameworks while driving innovation

 What We Want

• A leader who listens, learns, and leads with intention
• Someone who can balance strategic vision with operational execution
• A mentor who builds trust and grows talent
• A partner who sees technology as a tool—not a disruption

Who Are You?

You’re someone who can build on a strong foundation—someone who understands enterprise systems and knows how to guide them forward with clarity and purpose. You know how to spot opportunities, guide teams, and deliver results. You’re thoughtful, curious, and ready to make a meaningful impact.

Why You’ll Love It Here:

• We’re consistently ranked among the top 200 banks in the U.S. for employee engagement
• “Fun” isn’t just a buzzword—it’s a core value we live every day
• Competitive pay, great benefits, and real opportunities to grow
• A culture of giving back: we invest time and money into the communities we serve
• You’ll actually want to get up and come to work
• A collaborative executive team that values your input
• A stable tech foundation with room to grow

Why Join Us?

Because we’re building something great—and we want you to help us do it smarter. If you’re ready to lead with purpose, partner with passionate people, and make tech work for everyone, we’d love to hear from you.

Ready to join a team that’s serious about success—and just as serious about enjoying the ride?

Want to read more about why you should join the team, click the link below: 

Top 10 Reason You Should Explore a Career with Chesapeake Bank

Summary: 

The Chief Information Officer provides vision and leadership for developing and implementing information technology and business application initiatives. This position directs the planning and implementation of enterprise IT and Business Applications systems in accordance with the mission, core values, and purposes of the company.  In addition, this position also oversees the leadership of the Company’s data strategy and Project Management areas. 

• Develop vision and strategy for the Information Technology and Business Application teams to support the CFS Strategic Plan, including identifying key projects, goals, and objectives
• Foster a culture of continuous improvement, innovation, and employee development, providing guidance and mentorship to direct reports and all team members
• Responsible for senior oversight of the Information Technology, Business Applications, Data and Project Management areas
• Evaluates and determines the bank’s current and future technology, communications, and information needs through collaborative efforts throughout the organization
• Analyzes and controls all costs associated with the bank’s enterprise technology systems, communications and information systems
• Develop and maintain strong vendor relationships, negotiate contracts, and management of SLAs to ensure cost-effective and high-quality services
• Assess and manage risks related to technology implementation and recommend appropriate mitigation strategies
• Understand role as defined by the three lines of defense to maintain a compliance culture that includes risk management processes
• Other duties as assigned

• Four-year college degree with a technical, business or related field, or an equivalent combination of education and experience
• Strong analytical and financial skills
• Excellent interpersonal skills
• Extensive supervisory and managerial skills
• Strong technical skills with a minimum 10 years’ experience managing technical operations
• Ability to interact within all levels of the organization