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) 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) 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.
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) 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) Engineer provides live telephone and remote 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) Engineer's workday.
Within system/network administration support, the Level 2 (Human Support) 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) 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
- Perform large-scale and executive workstation deployments, and provide hardware support for workstations, servers, and network equipment
- Maintain client inventory records and approved client standard operating procedures
- Support on-site client dispatch
- 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
- Travel to client sites to provide on-site support as required
- Participate in the on-call rotation and technical training
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
- Hardware support for workstations, servers, and network equipment
Helpdesk/User Support Skills
- Professional telephone 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
Preferred Qualifications
- Demonstrated interest in the application of AI and automation to technology service delivery
KNOWLEDGE & CERTIFICATIONS:
Tooling Environment
- Microsoft 365
- NinjaRMM
- Autotask PSA
- AI-assisted ticket processing and automation frameworks
- Proficiency with Claude and other AI applications
Required Certifications
- CompTIA A+
- CompTIA Network+
- CompTIA Security+
Preferred Certifications
- Microsoft Endpoint Administrator (MD-102)
- Microsoft 365 / Entra ID certifications
Position:
- Location – Onsite in Rockville, MD
- Employment Type - Full time
- Compensation - $55,000-$72,000 DOE
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.
