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Senior Help Desk Specialist

Job in Frederick, Frederick County, Maryland, 21701, USA
Listing for: A Square Group (ASG)
Full Time position
Listed on 2026-10-17
Job specializations:
  • IT/Tech
    IT Support, HelpDesk/Support, Systems Administrator, Technical Support
Salary/Wage Range or Industry Benchmark: 70000 - 115000 USD Yearly USD 70000.00 115000.00 YEAR
Job Description & How to Apply Below
Company

Description:

ASG is a

Description

ASG is a Minority- and Woman-Owned, Physician-Owned small business with over 15 years of experience in federal government contracting. We deliver a wide range of technology services, including software development, mobile apps, AI/ML, analytics, data science, big data, Dev Sec Ops , digital transformation, cloud, and cybersecurity. ASG is CMMI Level 3 certified and holds ISO 9001:2015, 20000-1:2018, and 27001:2022 certifications.

Company

Description:

ASG is a Minority- and Woman-Owned, Physician-Owned small business with over 15 years of experience in federal government contracting. We deliver a wide range of technology services, including software development, mobile apps, AI/ML, analytics, data science, big data, Dev Sec Ops , digital transformation, cloud, and cybersecurity. ASG is CMMI Level 3 certified and holds ISO 9001:2015, 20000-1:2018, and 27001:2022 certifications.

Job Description

As a Senior Help Desk Specialist, you will provide advanced troubleshooting, platform expertise, and day-to-day continuity across Tier 1, 2 and Tier 3 support. This role does not carry supervisory responsibility, but functions as a trusted technical resource and informal point of reference for newer Specialists and for the Help Desk Manager. In addition to core ticket support, the Senior Specialist may be asked to lead new-user Slack orientation training and support Drupal and DKAN-based website content changes daily on behalf of the development teams.

Tier

Structure Overview:

Tier 1 -

Front-line intake and triage: login/access issues, basic content requests, routine how-to questions, initial ticket categorization.

Tier 2 -

Platform-specific troubleshooting: content and workflow issues, dynamic lists, redirects, broken links, collaboration tool support, moderate technical diagnosis.

Tier 3 -

Complex escalations: cross-platform issues, system-level troubleshooting, coordination with the Tools team or platform owners, and issues requiring developer or infrastructure-level investigation.

The Senior Help Desk Specialist primarily operates across Tier 2 and Tier 3, providing advanced troubleshooting and serving as an escalation point for other Specialists to contact when additional assistance is needed.

What You Will Do Advanced Ticket Support & Technical Escalation
  • Handle complex Tier 2 and Tier 3 tickets, including cross-platform issues and system-level troubleshooting.
  • Serve as a technical resource for Tier 1 and Tier 2 Specialists working through unfamiliar or difficult issues.
  • Provide day-to-day continuity for the Help Desk team when the Help Desk Manager is unavailable, routing urgent items appropriately and keeping work moving.
  • Support the Help Desk Manager in triaging escalations and identifying trends across ticket volume.
Website Development & Content Support (Drupal)
  • Perform Drupal-based website development and configuration changes in response to tickets submitted by the development team.
  • Support content publishing and workflow progression through the content management system.
  • Assist with testing of new installations, upgrades, and patches across supported platforms and enterprise-wide shared tooling.
Training & Knowledge Transfer
  • Deliver weekly “Slack 101” orientation training for CMS resources new to the WMS Program.
  • Maintain and update training and support materials for the collaboration and content management tools, incorporating changes as systems evolve.
  • Mentor newer Help Desk Specialists on platform tools, ticket handling standards, and program-specific procedures.
User Assistance
  • Provide user support for login issues, permissions, platform functionality, and web standards/policy guidance.
  • Support new user request intake and platform access processes.
Documentation &…
Position Requirements
10+ Years work experience
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