Merchant Services Specialist

Join Our Team as a Merchant Customer Service Specialist

Solve Problems. Support Businesses. Love What You Do.

If you’re someone who thrives on figuring things out, helping others, and keeping things running smoothly behind the scenes—we want to meet you. This is a fast-moving, high-impact role where no two days look the same and your work truly matters.

• A role where your work directly supports real businesses
• A collaborative team that actually enjoys working together
• Constant variety—new challenges, new solutions every day
• Opportunities to grow in a specialized, evolving industry
• A workplace where fun is part of the culture

• Naturally curious and quick to learn
• Detail-oriented and organized
• Calm, confident, and solution-focused
• Great at communicating and building trust
• Energized by a fast-paced environment

We’re known for high employee engagement and a culture that values both performance and people. At Chesapeake, you’ll find a team that supports your growth, celebrates your wins, and encourages you to bring your best every day.

• Competitive pay and comprehensive benefits
• Career growth and development opportunities
• A supportive, inclusive team environment
• The chance to make a real impact

If you’re ready for a role that’s equal parts people + problem-solving + purpose, apply now and let’s talk.

Chesapeake Payment Systems, a division of Chesapeake Bank, is a leading merchant acquirer based in Williamsburg, Virginia, delivering seamless card, ACH, gift, and loyalty payment solutions to businesses.

We are seeking a detail-oriented and tech-savvy Merchant Customer Service Specialist to support relationships with our merchant clients. In this role, you’ll be part of a collaborative, team-focused environment with the opportunity to grow within a specialized and evolving industry while supporting business clients and their payment solutions. This role is ideal for a quick learner who thrives in a fast-paced environment, stays focused under pressure, and enjoys helping others.

The Merchant Services Specialist plays a key role in delivering exceptional support, resolving issues, and ensuring the accuracy and integrity of merchant accounts.

• Provide comprehensive, high-quality support to merchants by responding to inquiries across multiple service channels (calls, emails, shared inboxes, and CRM tickets), ensuring efficient routing and timely resolution
• Support merchant onboarding by verifying account setup, complex pricing, and banking information
• Review customer files for accuracy, completeness and verify underwriting criteria
• Monitor and address account activity including disputes, chargebacks, compliance items, and processing alerts
• Understand your role as defined by the three lines of defense to maintain a compliance culture that includes risk management processes.
• Build strong relationships by understanding merchant needs, asking thoughtful questions, and identifying opportunities to enhance services
• Troubleshoot and resolve issues related to payment processing systems, terminals, and eCommerce platforms
• Perform additional duties and special projects assigned

• Minimum of 2 years of customer service experience in an office setting.
• Merchant Services or Payments experience preferred.
• Strong written and verbal communication skills
• Proficiency in Microsoft 365 (Outlook, Word, Excel) and Microsoft Teams; CRM experience a plus
• Demonstrated ability to quickly learn new software, systems, and processes
• Strong attention to detail and organizational skills
• Analytical thinking with the ability to troubleshoot and resolve complex issues
• Ability to prioritize a changing workload in a fast-paced environment
• Self-motivated and able to work both independently and collaboratively
• Valid Driver’s License
• Willingness to travel locally to merchant locations as needed