[Hiring] Level 2 Engineer @OSIbeyond

Role Description

The Level 2 (Human Support – Remote) Engineer is responsible for the delivery of high-quality technical support to OSIbeyond clients across two service domains: helpdesk/user support and system/network administration support. This is a fully remote position: all support is delivered by telephone, video, and remote session, and work requiring physical presence at a client site or OSIbeyond headquarters is handed off to office-based Level 2 (Human Support) or Level 2 (Onsite Augmentation) staff.

• Helpdesk/User Support – Automated Workflow Oversight for Non-Regulated Clients (approximately 90% of helpdesk requests)
  • Review request parameters identified by AI-assisted ticket processing, or complete the associated request form, and confirm accuracy prior to execution.
  • Authorize and initiate approved automation workflows and verify successful completion.
  • Identify and correct inaccurate or incomplete request data before changes are applied to client environments.
  • Request categories fulfilled through automation include:
    • License assignment
    • BitLocker recovery key retrieval
    • Local Administrator Password Solution (LAPS) credential retrieval
    • Multi-factor authentication reset
    • Microsoft 365 password reset
    • Shared mailbox permission management
    • Distribution list creation, modification, and removal
    • Automatic reply (Out of Office) configuration
    • Calendar permission management
    • User onboarding and offboarding
    • Workstation setup
  • Perform these tasks manually only by exception, and report request types that recur outside the scope of existing automation.
  • Identify recurring manual tasks and submit them to the Automation Engineer for automation evaluation.
  • Participate in the testing and validation of new automation and AI workflows prior to release to the support team.
• Helpdesk/User Support – Live Technical Support (approximately 10% of helpdesk requests)
  • Respond to inbound support calls from client personnel and serve as the primary point of contact for requests not addressed through automation.
  • Complete remote sessions automatically scheduled to their calendar by the scheduling automation tool when a client submits a request requiring a remote session.
  • Deliver remote support using approved tools, including RMM-based and ad hoc remote sessions, and provide guided assistance where remote access is unavailable.
  • Install non-standard software not deployed through the standard Autopilot configuration.
  • Diagnose and resolve application and workstation issues, including Microsoft 365 desktop applications.
  • Provide end-user guidance and instruction on Microsoft 365 and standard business applications.
  • Perform initial network connectivity troubleshooting, including workstation connectivity, wireless, VPN, and home internet service issues.
  • Use Claude AI to search the internal document management system (DMS) and external resources when diagnosing issues and locating standard operating procedures.
  • Identify requests requiring escalation and route them in accordance with established procedures.
• System/Network Administration Support
  • Resolve system/network administration requests and escalations across client environments.
  • Administer Microsoft 365, Microsoft Entra ID, and Active Directory within the defined scope of the role.
  • Provision accounts for executive personnel, special circumstances outside the scope of standard onboarding automation, and clients subject to regulatory compliance requirements.
  • Administer SharePoint Online permissions, and create standard SharePoint sites, with appropriate oversight.
  • Execute migration tasks in accordance with documented procedures provided by senior engineering staff.
  • Troubleshoot server connectivity, including Remote Desktop access, approved vendor remote sessions, and reported outage review.
  • Support large-scale and executive workstation deployments through remote provisioning, configuration, and post-deployment validation, and coordinate hardware replacement and other physical work with on-site staff.
  • Maintain client inventory records and approved client standard operating procedures.
  • Provide remote diagnosis and complete handoff documentation when a request requires on-site dispatch, and coordinate with on-site staff through resolution.
  • Execute documented security incident response procedures.
• General Responsibilities
  • Complete assigned tickets and remote sessions in accordance with standard operating procedures and applicable service level agreements.
  • Maintain accurate, complete documentation and ticket records for all work performed.
  • Maintain an orderly, prioritized ticket queue and notify the VP of Technical Services when workload exceeds capacity.
  • Coordinate remote session scheduling through the ticketing system and arrange carrier pickup of client workstations as required.
  • Participate in the on-call rotation and technical training.
  • Maintain availability during scheduled support hours (Eastern Time) from a dedicated, private workspace with reliable high-speed internet suitable for client phone and video calls.
  • Work only from company-managed equipment and approved network connections, and secure equipment and client information in the remote work environment in accordance with OSIbeyond remote work and information security policies.

Qualifications

• System/Network Administration Skills
  • Microsoft 365 administration (Exchange Online, Entra ID, SharePoint Online)
  • Active Directory and identity management
  • DFS and SharePoint Online permission management
  • Networking fundamentals (VPN, DNS, connectivity)
  • Remote Desktop and server connectivity troubleshooting
  • Ability to guide on-site personnel through basic hardware tasks remotely (cabling, peripheral replacement, power cycling)
• Helpdesk/User Support Skills
  • Professional telephone, video, and written communication with users of varying technical proficiency
  • Microsoft 365 desktop application troubleshooting
  • Windows endpoint troubleshooting and software installation
  • Remote support tools, including RMM-based and ad hoc remote sessions
  • Workstation provisioning and deployment (Autopilot)
• Automation & Operational Skills
  • Ability to execute, verify, and interpret the output of scripted and automated workflows
  • Sound judgment in identifying inaccurate AI-generated data and requests requiring manual handling
  • Proficiency with professional services automation (PSA) and RMM platforms
  • Adherence to documentation standards and standard operating procedures
  • Understanding of least privilege and access control principles
  • Incident response awareness

Requirements

• A minimum of two years of hands-on technical support experience, including system/network administration responsibilities, preferably in a managed services or multi-client environment.
• Ability to manage multiple priorities in a fast-paced environment.
• Strong attention to detail in documentation and audit readiness.
• Demonstrated ability to work independently and remain productive without in-person supervision.

Preferred Qualifications

• Demonstrated interest in the application of AI and automation to technology service delivery.
• Prior experience in a fully remote technical support role.

Working Conditions

• Fully remote position; must reside in a U.S. state in which OSIbeyond employs remote staff and work core support hours in Eastern Time.
• Dedicated, private workspace with reliable high-speed internet that meets OSIbeyond remote work policy requirements.
• Occasional travel to Rockville, MD headquarters for onboarding, training, or team meetings as required.

Benefits

• Medical Insurance - OSIbeyond pays 75% of the premium for the Employee's base medical plan.
• Vision and Dental Insurance - OSIbeyond pays 75% of the premium for the Employee's plans.
• Life Insurance - OSIbeyond pays 100% of the premium for the Employee's plans.
• Short Term Disability Insurance - OSIbeyond pays 100% of the premium for the Employee's plans.
• 401K - OSIbeyond matches up to 4%.
• PTO/Holidays - 9 paid Holidays and accrual based PTO which increases with tenure, new hires start out with 2 weeks.