Weekend Helpdesk Jobs in Virginia (NOW HIRING)

The Support Services Supervisor is responsible for the day-to-day supervision and coordination of customer support operations serving internal and external customers, including technology service desk functions. This role oversees staff performance, service quality, ticket and call management, escalations, training, and knowledge management to ensure timely and effective customer support.

The position provides hands-on leadership to the support team, monitors service activity and performance, addresses escalated issues, and works with the Support Services Manager and other departments to identify and resolve recurring service issues and improve support processes.

Key Responsibilities

Team Supervision & Daily Operations

• Supervise the day-to-day activities of the Support Services team, including customer service and technology service desk functions.
• Coordinate daily workloads and assignments to ensure appropriate coverage and timely response to customer needs.
• Monitor calls, emails, voicemails, and support tickets to ensure requests are addressed promptly and appropriately.
• Provide direction and support to team members throughout daily operations.
• Assist with scheduling and coverage needs to maintain appropriate service levels.
• Promote consistent application of established support procedures, standards, and policies.

Service & Ticket Management

• Monitor the support queue and review tickets for appropriate documentation, prioritization, assignment, follow-up, and resolution.
• Track call volume, ticket volume, response times, handling rates, voicemail activity, and other established service measures.
• Identify aging, unresolved, or recurring support issues and ensure appropriate follow-up or escalation.
• Help ensure established service expectations and response standards are consistently met.
• Review support activity to identify opportunities to improve service quality and efficiency.

Customer Escalations

• Serve as an escalation point for complex, sensitive, or unresolved customer issues.
• Assist team members with problem resolution and provide guidance on appropriate next steps.
• Maintain clear and professional communication with customers throughout escalated situations.
• Coordinate with other departments or technical resources when additional expertise is required.
• Ensure escalated issues are appropriately documented and followed through to resolution.

Employee Coaching & Training

• Provide ongoing coaching, feedback, and support to team members.
• Assist with onboarding and training new employees.
• Identify individual and team training needs and help develop appropriate training materials and resources.
• Reinforce customer service expectations, support procedures, and documentation standards.
• Work with management to address performance concerns and support employee development.

Knowledge Management & Process Improvement

• Maintain and update knowledge base content, procedures, and support documentation as products and processes change.
• Identify recurring customer issues, service gaps, and opportunities for process improvement.
• Partner with other departments to address recurring problems and improve the customer support experience.
• Help develop and maintain standardized procedures and workflows for support operations.
• Encourage knowledge sharing and consistent use of documented support practices across the team.

Reporting & Management Support

• Work with the Support Services Manager to provide updates on team performance, service activity, customer issues, and areas requiring attention.
• Assist with compiling and reviewing support metrics and operational information.
• Identify trends and recommend practical improvements to service delivery and team processes.
• Support departmental initiatives and projects as assigned.

After-Hours Support

• Be available for after-hours and weekend escalations involving emergencies, urgent customer issues, or critical support matters, as required.
• Coordinate with appropriate internal resources when an issue requires additional technical or management support.

Qualifications

• High school diploma or equivalent required; associate or bachelor's degree in Business, Information Technology, Communications, or a related field preferred.
• Minimum 5 years of experience in customer service, technical support, helpdesk, service desk, or call center operations.
• Previous supervisory or team lead experience required.
• Experience with ticketing, helpdesk, or customer support systems.
• Experience working with call center or support service metrics.
• Experience maintaining knowledge bases, procedures, or other support documentation.
• Experience coaching, training, and developing employees.
• Experience handling customer escalations and difficult service situations.
• Experience supporting both internal and external customers preferred.

Core Skills

• Strong customer service and service delivery skills.
• Effective team supervision and employee coaching.
• Strong verbal and written communication skills.
• Sound judgment and problem-solving abilities.
• Ability to handle escalated customer situations professionally and effectively.
• Strong organizational and time-management skills.
• Ability to prioritize competing responsibilities in a fast-paced support environment.
• Strong attention to detail and follow-through.
• Understanding of ticket management and customer support workflows.
• Ability to interpret service metrics and identify operational issues.
• Ability to work collaboratively across departments.
• Comfortable providing hands-on support and direction to team members as needed.

Work Environment & Expectations

Work may be performed in an office environment, hybrid setting, or fully remote depending on business needs. The position requires regular interaction with employees, customers, and other departments through phone, email, ticketing systems, and other communication platforms.

The Support Services Supervisor must be available for occasional after-hours and weekend escalations involving emergencies, urgent customer issues, or critical support matters. Extended hours may occasionally be required based on service needs.

Disclaimer

This job description is intended to describe the general nature and level of work being performed. It is not intended to be an exhaustive list of all responsibilities, duties, or qualifications. Responsibilities and duties may change at any time, with or without notice, to meet business needs. Employees may be required to perform additional duties as assigned.

Benefits

CherryRoad offers a comprehensive benefits package for full-time employees that includes health insurance (medical, dental, and vision), paid time off, paid sick time, paid holidays, and a 401(k) retirement plan with employer contributions. Part-time employees are eligible for paid sick time and participation in the 401(k) plan.

Equal Opportunity Employer Statement

CherryRoad is an Equal Opportunity Employer. We consider all qualified applicants without regard to legally protected characteristics, including race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected category under federal, state, or local law.