Chesapeake Financial Shares, Inc.

Merchant Technology Specialist

5000 Foundation St
Customer Service/Support


Chesapeake Bank


Want to work for a solid financial institution that expects 110% from its employees and rewards them accordingly? We work as a team and have high levels of engagement from our employees. A primary driver of engagement is job satisfaction. Contributors to this high level of job satisfaction are the Chesapeake benefits plan from competitive healthcare options to a generous vacation allotment. Commitment to community also plays into our job satisfaction. Chesapeake puts great emphasis on the fact that we are only as strong as the communities we serve. Therefore, we contribute dollars and hours of service to our local communities. And, we have fun doing it all!


Talk to us about a career that makes you want to get up and come to work, have fun and make a difference.


Summary:  The role of a Merchant Technology Specialist is best suited for a motivated, dependable, team player who thrives in a fast-paced work environment. Chesapeake Payment Systems faces new challenges on a daily basis so it is crucial that all employees embrace change and have the ability to adapt and learn new skills.


  • Resolve customer service inquiries.
  • Assist with merchant POS programming and testing.
  • Provide technical assistance and troubleshooting to merchants and bank personnel.
  • Provide training and customer service to merchants and bank personnel.
  • Assist with all types of POS installations requiring local travel.
  • Possess adequate knowledge to configure routers, printers etc.
  • Assist merchants with validating PCI Compliance.
  • Maintain inventory.
  • Maintain leadership knowledge with Restaurant/Retail POS solution.
  • Listen to merchant conversation and understand their needs to provide solutions.
  • Research to find solutions for merchant needs like new equipment or software products.
  • Research to find solutions for Merchant Support Team needs.
  • Work with branch staff and business development officers to satisfy customers’ needs
  • Other duties as assigned.


  • Minimum 2 years customer service experience.
  • Merchant Services experience a plus.
  • Excellent written and oral communications skills.
  • A “Can Do” attitude.
  • Ability to work independently and in a team environment.
  • Proficient with Microsoft Office applications including Outlook, Word, Access, and Excel.
  • Aptitude to learn new software programs and job functions.
  • Demonstrate strong attention to detail.
  • Intuitive with an aptitude to problem solve complex situations.
  • Ability to lift 50lb boxes to assist with inventory control.
  • Willingness to travel to merchant location as necessary.


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