Chesapeake Bank - Chesapeake Payment Systems

Join Our Team as a Merchant Technology Specialist I

Are you passionate about technology and customer service? Chesapeake Payment Systems is seeking a Merchant Technology Specialist I to provide hands-on technical support for payment systems, including hardware, software, and networking components. This role is ideal for a dependable, solutions-oriented team player who thrives in a fast-paced, ever-evolving environment.

What You’ll Do:

• Deliver first-line troubleshooting for card processing, point-of-sale systems, and software solutions.
• Provide responsive and helpful support for merchant inquiries.
• Track and manage service progress using Chesapeake Bank and Chesapeake Payment Systems CRMs.
• Collaborate with prospects and customers to develop creative strategies for accepting payments.
• Adapt quickly to new challenges, technologies, and learning opportunities.

What We’re Looking For:

• Strong problem-solving and questioning skills.
• Excellent customer service and communication abilities.
• Motivation to learn and grow in a dynamic technical environment.
• Ability to embrace change and apply new skills immediately.

Why Chesapeake?

We’re a team that values innovation, collaboration, and continuous improvement. If you’re ready to make an impact and grow your career in merchant services technology, we’d love to hear from you.

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

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

Apply Today!

• Provide first-level technical support and training for various payment systems, including physical
  terminals, POS systems, and online gateways
• Assist with the configuration, installation, and ongoing maintenance of implemented payment systems via
  phone, in-person, email, or video conferencing
• Diagnose and resolve technical issues related to software and hardware malfunctions, network
  connectivity problems, and general payment errors via phone, in-person, email, or video conferencing
• Develop proficiency in operating and maintaining multiple payment processing systems and CRMs
• Escalate complex technical issues to the specialized teams or vendors for advanced resolution
• Maintain detailed records of client and partner support interactions and troubleshooting activities within
  the CRM and ticketing system
• Collaborate with a team in-office to achieve shared goals and objectives
• Manage equipment tracking and inventory
• Assist with the preparation of monthly, quarterly, and yearly reports
• Assist with monitoring merchant risk and card chargebacks
• Review customer files for accuracy, completeness, and verify underwriting criteria
• Review customer statements for pricing accuracy and assist in completing pricing analyses and
  presentations for merchants
• Perform other related duties as assigned to support the merchant services department
• Understand your role as defined by the three lines of defense to maintain a compliance culture that
  includes risk management processes

• Minimum 1-2 years of experience in a technical-support or help-desk environment
• Knowledge and experience with POS systems and/or credit card terminals preferred
• Associate’s degree or equivalent work experience required
• Exceptional problem-solving, analytical, organizational, and time management skills
• Highly motivated, goal-oriented, and persistent with a strong work ethic
• Excellent verbal and written communication skills for effective customer and internal team interaction
• Intermediate proficiency of Microsoft Office programs (word, Excel, Outlook)
• Basic to Intermediate level understanding
• Ability to travel up to 25% of total working hours to merchant locations
• Ability to lift up to 25lbs with or without assistance
• Ability to perform well under pressure in a fast-paced environment