IT Specialist / Help Desk

Overview

MyPlanAdvocate is seeking a detail-oriented and service-driven IT Specialist / Help Desk professional to support day-to-day technology operations. This role ensures employees have reliable, secure access to the systems and tools necessary for success. It's ideal for someone who thrives in a fast-paced environment, enjoys solving technical issues, and is passionate about delivering a positive user experience.

You will serve as the frontline support resource for IT needs across the organization, managing user access, troubleshooting devices, maintaining security standards, and coordinating with internal teams to resolve technical issues efficiently. The ideal candidate combines strong technical troubleshooting skills with excellent communication and a customer-first mindset.

Why Join Us

• Opportunity to shape and scale a rapidly growing technical organization
• High-visibility role partnering directly with senior leadership
• Collaborative and mission-driven culture
• Ability to influence long-term strategy and operational direction
• Meaningful ownership across systems, processes, and cross-functional outcomes

Job Duties for the IT Specialist / Help Desk

• Manage onboarding and offboarding processes, ensuring users receive appropriate access to systems, including O365, email, licensing, dynamic groups, and internal applications.
• Provide day-to-day technical support, including password resets, account access issues, and troubleshooting hardware, software, and connectivity problems.
• Configure, maintain, and troubleshoot laptops and devices, ensuring systems are secure, compliant, and functioning properly.
• Maintain and update help desk documentation, knowledge base articles, and resolution procedures to improve support efficiency and knowledge sharing.
• Monitor and manage device health using Atera and respond to alerts related to performance, patching, and system reliability.
• Support security operations by responding to alerts from SentinelOne, Rippling, and Arctic Wolf; escalate and initiate emergency contact procedures for high-risk threats.
• Assist with email whitelisting and spam filtering to ensure secure and reliable communication.
• Perform O365 licensing audits and cleanup to maintain cost efficiency and compliance.
• Monitor Arctic Wolf cloud and device security scans and assist with remediation efforts as needed.
• Handle and triage help desk tickets, resolving issues directly or routing to the appropriate team (Data, Engineering, HR, or other departments).
• Redirect HR-related requests through the proper HR request process to ensure compliance and proper tracking.
• Monitor Teams and internal communication channels for user-reported issues and proactively assist when problems arise.
• Support SSO configuration and access management across integrated systems.
• Collaborate with internal teams to resolve Looker/data access issues and other cross-functional technical requests.
• Maintain accurate records of IT issues, resolutions, and recurring patterns to improve response times and prevent future incidents.
• Provide user guidance and basic training to promote best practices in security, system usage, and self-service troubleshooting.

What you’ll bring!

• 5+ years of experience in IT support, help desk operations, or technical support roles.
• Strong verbal and written communication skills with the ability to explain technical concepts clearly to non-technical users.
• Customer-first mindset with a professional, patient, and solutions-oriented approach to user support.
• Experience managing user onboarding/offboarding and access provisioning across multiple systems.
• Familiarity with Single Sign-On (SSO) configuration and identity/access management best practices.
• Experience administering Microsoft 365, including licensing, groups, and access management.
• Experience supporting cloud environments such as Azure, AWS, or GCP (preferred).
• Experience working with endpoint monitoring and management tools (such as Atera or similar platforms).
• Familiarity with endpoint security and threat detection tools such as SentinelOne, Arctic Wolf, or similar security platforms.
• Ability to identify, prioritize, and escalate security risks appropriately.
• Experience documenting technical procedures and maintaining knowledge base resources.
• Strong troubleshooting skills across hardware, operating systems, networking, and common business applications.
• Ability to manage multiple requests, prioritize effectively, and remain organized in a fast-paced environment.
• Call center or high-volume support environment experience is a plus.
• Commitment to maintaining security, confidentiality, and compliance best practices.

Telecommuting Requirements

• Ability to keep all company-sensitive data secure.
• Required to have a dedicated work area established that is separated from other living areas and provides information privately without disruption.
• Must live in a location that can receive a high-speed internet connection or leverage an existing high-speed internet service.

What we offer!

• Paid Time Off.
• Paid Company Holidays.
• Medical, Dental, Vision, Life Insurance, HSA, FSA, and more.
• 401 (K) savings plan with company matching up to 3%.
• Work-Life Resources
• Discounts with Hotels, Rental Cars, Entertainment, Attractions, & More!
• Maternity/Paternity/Adoption paid leave.
• Referral program.
• Company-supplied computer equipment.

Key skills/competency

• IT Support
• Help Desk Operations
• Technical Troubleshooting
• User Access Management
• Microsoft 365 Administration
• Endpoint Security
• Atera
• SentinelOne
• Arctic Wolf
• SSO Configuration