Level 2 Engineer (Human Support)

OSIbeyond • Rockville, MD

3d • Remote

About The Position

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. Within helpdesk/user support, approximately 90% of requests are fulfilled through automated workflows. Certain requests received by phone are fulfilled by completing a request form that initiates the corresponding automation. For these requests, the Level 2 (Human Support – Remote) Engineer serves as the point of human validation, reviewing the request parameters identified by the AI-assisted ticketing process, confirming their accuracy, authorizing execution of the automated workflow, and verifying the outcome. Clients subject to regulatory compliance requirements are excluded from automated fulfillment; requests for these clients are completed manually. The remaining requests, approximately 10%, require direct engagement with the end user. For these, the Level 2 (Human Support – Remote) Engineer provides live telephone, video, and remote-session support, taking ownership of the request from initial contact through resolution. Although live support represents roughly 10% of helpdesk request volume, it accounts for approximately 80% of the Level 2 (Human Support – Remote) Engineer's workday. Within system/network administration support, the Level 2 (Human Support – Remote) Engineer resolves administrative requests and escalations involving identity, Microsoft 365, server, and network environments, operating within established procedures and escalating to senior engineering staff where appropriate. These advanced tasks will be completed through the use of various tools and Standard Operating Procedure documents. As OSIbeyond continues to engineer additional automation and AI capabilities into the OSIbeyond ONE platform, the scope of helpdesk/user support work fulfilled through automation is expected to expand. The Level 2 (Human Support – Remote) Engineer contributes to this progression by identifying recurring manual work suitable for automation, coordinating with automation engineers, and validating new workflows prior to and following release. Performance in this role is measured by client satisfaction, adherence to service level agreements, the accuracy and timeliness of automated workflow execution, first-contact resolution of live support requests, and the quality and completeness of documentation.

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
• 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)
• 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)
• 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
• CompTIA A+
• CompTIA Network+
• CompTIA Security+

Nice To Haves

• Demonstrated interest in the application of AI and automation to technology service delivery
• Prior experience in a fully remote technical support role
• Microsoft Endpoint Administrator (MD-102)
• Microsoft 365 / Entra ID certifications

Responsibilities

• 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
• Perform 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
• Respond to inbound support calls from client personnel and serve as the primary point of contact for requests not addressed through automation
• 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
• 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
• 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
• Complete required training and maintain awareness of cybersecurity risks including insider threats and handling of regulated data.
• Treat company and client data as confidential and follow all applicable security and information protection policies.
• Follow cybersecurity procedures outlined in company policies and the employee handbook.
• Immediately report and follow incident response procedures for any suspected security incidents.
• This position follows established policies and procedures to keep confidential information secure.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed