Level 2 Engineer (Human Support) - Remote

Since 2004, OSIbeyond has provided managed technology and cybersecurity services to commercial organizations, nonprofits, associations, and government contractors, guided by a founding principle that outstanding technical expertise must be matched by an exceptional client experience. That commitment is delivered today through OSIbeyond ONE, an integrated technology platform that unifies IT operations, cybersecurity, Microsoft 365, cloud services, automation, artificial intelligence, and expert support within a single, continuously managed operating environment.

The platform is founded on a defined operating philosophy: Automation First. AI Enabled. People Powered.

Within OSIbeyond ONE, routine technology requests are increasingly fulfilled through intelligent monitoring, AI-assisted ticket processing, and automated service workflows, and OSIbeyond continuously invests in expanding these capabilities. The Level 2 (Human Support – Remote) Engineer represents the human expertise at the center of this model. The position provides oversight and authorization for automated helpdesk/user support workflows, delivers live technical support to end users when automation is not applicable, and performs system/network administration support across a diverse portfolio of client environments.

This position is intended for an accomplished technical professional who seeks to apply their expertise within a modern, automation-driven service delivery model. The successful candidate will demonstrate sound technical judgment, a commitment to accuracy and accountability, professionalism in client communication, and an interest in the continued advancement of AI and automation in managed technology services.

About the Role:

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.

ESSENTIAL DUTIES:

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

SUCCESS METRICS:

Client satisfaction across automated and live support interactions

Key Performance Indicator adherence and ticket quality

Accuracy of automated workflow execution

Call responsiveness and first-contact resolution rate for live support requests

Average resolution time for helpdesk/user support and system/network administration requests

Utilization of internal tools to locate proper SOPs and documentation independently

Documentation completeness and quality

Recurring manual tasks identified and submitted for automation evaluation

SECURITY RESPONSIBILITIES:

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.

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

Required Qualifications

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 Qu