Senior Help Desk Specialist

JOB TITLE: Help Desk Specialist (Senior)

DIVISION: Government Services — MDVOTERS Project

LOCATION: Hybrid remote — Baltimore, MD (occasional on-site presence required for MDVOTERS support)

EMPLOYMENT: Full-Time; 1099 Independent Contractor (via TCG vendor partner) — with potential FTE conversion, depending on budget & performance

REPORTS TO: MDVOTERS Project Lead (TCG) and Vendor Partner Account Manager

About Us

The Canton Group is a privately held, family-owned company with over 25 years of delivering award-winning websites, software, and digital modern secure solutions to Fortune 500 organizations and Government entities. We take immense pride in offering our employees the benefit of working fully remote while our Headquarters remain open in Baltimore, Maryland. The Canton Group's presence spans across the nation, including our employees and clients. Apply today and join us on our journey of growth!

Our Core Values

Intellectually Curious | Committed to doing things the right way | Transparent, Honest, and Fair | Determined to delight our customers | Be Collaborative & Accountable

Important — Engagement Structure

Please read carefully: this role's employment structure differs from most positions at The Canton Group. While most TCG positions are hired and employed directly through TCG, this Help Desk Specialist (Senior) opening will be engaged through TCG's vendor partner as a 1099 independent contractor to support the MDVOTERS project. The selected candidate will work alongside the TCG team and contribute to a TCG-led client engagement, but the initial independent contractor relationship will be with our vendor partner — not directly with TCG. There is the potential for this 1099 contractor role to convert into a full-time employee (FTE) position with TCG or the client, contingent on budget, project needs, and demonstrated performance during the contract. Conversion is not guaranteed and timelines vary.

Overview

The Help Desk Specialist (Senior) is a frontline support role on the MDVOTERS project, the platform that supports Maryland's voter registration and election administration work. This role serves as the initial point of contact for end users, providing telephone and in-person support across directories, standard Windows desktop applications, and the custom applications developed under this Contract and its predecessors. The Help Desk Specialist (Senior) is responsible for troubleshooting hardware, software, PC, and printer issues, and for resolving tier 0/I incidents efficiently, professionally, and with a consistently positive customer service attitude.

Reporting jointly to the MDVOTERS Project Lead at The Canton Group and the Vendor Partner Account Manager, the Help Desk Specialist (Senior) operates with the calm professionalism expected in a state government environment. This role works closely with election officials, end users at client agencies, and the broader MDVOTERS delivery team, balancing the urgency of frontline support with the disciplined documentation, escalation, and security practices required of a state voter information system.

The Help Desk Specialist (Senior) is not a back-office role. The emphasis is on direct end-user engagement: diagnosing problems quickly, communicating clearly with users of varying technical backgrounds, and consistently following through. This frontline credibility is what makes the help desk function an essential layer of the MDVOTERS support model, protecting end-user productivity during routine operations and during the high-pressure conditions of an active election cycle.

Responsibilities

Reasonable accommodation may be provided to enable individuals with disabilities to perform these essential functions.

End-User Support & First-Contact Resolution

• Provide telephone and in-person support to users in the areas of directories, standard Windows desktop applications, and applications developed under the MDVOTERS Contract and its predecessors.
• Serve as the initial point of contact for troubleshooting hardware and software issues across PCs and printers, resolving tier 0/I incidents at first contact whenever possible.
• Escalate complex issues to the appropriate tier or specialist team with clear, complete handoff information, ensuring continuity of support for the end user.
• Communicate clearly and empathetically with end users of varying technical backgrounds, ensuring a consistently positive support experience even under pressure.

Hardware, Software & Printer Troubleshooting

• Diagnose and resolve PC hardware issues, peripheral problems, and printer faults common in a state government office environment, including imaging, driver, and connectivity issues.
• Troubleshoot standard Windows desktop applications, Microsoft 365 productivity tools, and the custom MDVOTERS application suite, distinguishing between user error, configuration issues, and product defects.
• Support user account activities — directory lookups, password resets, and access requests — within established protocols, with attention to identity verification and access control discipline.
• Coordinate with desktop engineering and infrastructure teams to resolve issues that require elevated access, vendor engagement, or environment-level changes.

Ticket Documentation & Knowledge Management

• Maintain accurate, timely, and complete ticket documentation in the help desk system, including reproduction steps, root cause (where known), and resolution details.
• Contribute to knowledge base articles, FAQs, and internal runbooks to improve first-contact resolution rates and reduce repeat incidents over time.
• Identify recurring issues and surface trend data to project leadership so root causes can be addressed at the platform, training, or process layer.
• Track and report on personal ticket metrics — including volume, SLA attainment, and resolution rate — as required by the project and the vendor partner.

Customer Service & Stakeholder Engagement

• Represent both The Canton Group and the vendor partner professionally with State of Maryland end users, election officials, and project stakeholders.
• Demonstrate a positive, professional customer service attitude in every interaction, particularly during high-pressure periods such as active election cycles and statewide elections.
• Communicate proactively with end users on incident status, expected resolution times, and follow-up actions, setting clear and realistic expectations.
• Build credibility with the project team as a dependable, follow-through-driven support professional whom both Product and Engineering teams can trust as the user's voice.

Security, Compliance & Confidentiality

• Adhere to all client security policies, procedures, and controls appropriate to a state voter information system, including the handling of personally identifiable information (PII).
• Comply with all background check, access control, and acceptable use requirements established by the client, The Canton Group, and the vendor partner.
• Handle confidential information in accordance with MDVOTERS, State of Maryland, and TCG vendor partner requirements, escalating any potential security concerns promptly.
• Adhere to the organization's security policies, procedures, and controls to protect confidential information and ensure compliance with applicable state and federal requirements.

Qualifications

• Bachelor's degree from an accredited college or university with a major in Computer Science, Information Systems, Engineering, Business, or another related scientific or technical discipline; OR three (3) years of equivalent experience in a call center, customer service, and/or tier 0/I help desk support environment.
• Minimum of five (5) years of experience in a business IT environment with emphasis on PC computer hardware and applications.
• At least five (5) years of comprehensive, hands-on knowledge of PC operating systems and working in a help desk function.
• Demonstrated ability to communicate effectively, both orally and in writing, with end users of varying technical backgrounds.
• Consistently positive, professional customer service attitude, even under pressure during peak operational periods.
• Strong analytical and troubleshooting skills, with the ability to diagnose and resolve issues efficiently across hardware, software, and applications.
• Ability to work independently as a 1099 independent contractor while collaborating effectively with the TCG project team, vendor partner, and client stakeholders.

Preferred Qualifications

• Direct experience supporting state, local, or federal government end users or projects.
• Familiarity with ITIL practices or other formal help desk and incident management methodologies.
• Experience with common ticketing platforms (e.g., ServiceNow, Jira Service Management, Zendesk, Remedy).
• Exposure to Active Directory, Microsoft 365 administration basics, and standard imaging and deployment tools.
• Relevant certifications such as CompTIA A+, Network+, HDI Support Center Analyst, or Microsoft 365 Certified: Fundamentals.
• Prior experience working as a 1099 independent contractor on a government or public-sector engagement.

Physical Requirements

• Prolonged periods sitting at a desk and working on a computer.
• Must be able to lift 15 pounds at a time.
• May be required to work on-call or long hours, if necessary, in case of serious network malfunction or election-period incident response.