Level 3 Escalation Projects Engineer - Remote

Since 2004, OSIbeyond has delivered managed technology and cybersecurity services on a founding principle: outstanding technical expertise, matched by an exceptional customer experience. Today, that commitment is delivered through OSIbeyond ONE, our integrated technology platform that unifies IT operations, cybersecurity, Microsoft 365, cloud, automation, AI, and expert support into a single, continuously managed environment. The platform is built on a clear operating philosophy: Automation First. AI Enabled. People Powered.

Within that model, the overwhelming majority of routine service requests are resolved by automation, with the Level 2 (Human Support) team confirming AI-extracted parameters and initiating workflows. What remains is, by definition, the hard part: the intermittent fault that spans identity, network, and application layers; the migration that touches every user in an organization; the server, firewall, or hybrid cloud dependency that no runbook anticipated. The Level 3 Engineer is where that work lands, and where it gets solved.

This is the senior engineering seat in Technical Services. The Level 3 Engineer is the escalation authority for the Level 2 team, the engineer who scopes, leads, and delivers client infrastructure projects, the steward of OSIbeyond’s own internal infrastructure, and a working partner to the Automation Engineering team in deciding what gets automated next. Every escalation resolved here is also studied here: the engineer is expected to ask whether a class of problem should ever reach a human again, and to help design the workflow, detection, or self-healing logic that ensures it does not.

The position spans a range of seniority. Engineers at the earlier end of that range concentrate on resolving the most complex escalations and executing pre-scoped project work to a high standard. Engineers at the senior end own project scoping and delivery, direct the work of peers on complex migrations, design architecture, and carry a larger share of automation design and technical leadership. Compensation and scope of ownership grow with demonstrated expertise and impact within the position.

This position is suited to a technically accomplished engineer who has outgrown ticket volume and wants ownership of the difficult, consequential work: complex escalations, infrastructure and project delivery, and the engineering of automation that lifts an entire team. The successful candidate combines deep Microsoft 365, Azure, Windows Server, and network expertise with sound judgment under pressure, disciplined documentation, and the professionalism to represent OSIbeyond in front of client leadership during a high-stakes incident or a major project cutover.

About the Role:

The Level 3 Engineer resolves the complex, high-priority, and urgent escalations that exceed the scope of automation and the Level 2 team; scopes, leads, and delivers client technology projects; designs, deploys, and maintains client infrastructure across on-premises, Microsoft 365, and Azure environments; and completes the internal projects and maintenance that keep OSIbeyond’s own infrastructure and operations secure and current.

The engineer owns the escalation queue end to end. Each escalation is triaged for business impact, diagnosed to root cause rather than symptom, resolved within service level commitments, and documented so that the resolution becomes reusable knowledge, an updated procedure, or a specification for new automation. Where an automated workflow has failed or produced an unexpected result, the Level 3 Engineer is the engineer who determines why, corrects the environment, and works with Automation Engineering to harden the workflow.

On the project side, the Director of Engineering leads discovery and scoping, and the engineer takes the work from there through delivery: solution design, detailed implementation plans, cutover execution, post-project validation, and client-facing training on what was delivered. Projects range from server, network, and identity deployments to tenant and data migrations and cloud modernization. The engineer prepares the detailed directions that allow peers to execute project tasks reliably, and manages scope, schedule, and client communication throughout.

Across all of this work the engineer uses OSIbeyond-approved AI assistants to accelerate diagnostics, scripting, planning, and documentation, and holds every AI-assisted output to the same standard of verification as any other engineering work. The Level 3 Engineer also raises the technical ceiling of the team through mentorship, peer review, and the on-call rotation. Performance is measured against escalation quality and timeliness, SLA adherence, project delivery, client satisfaction, documentation standards, and the volume and value of automation the engineer helps bring into production.

ESSENTIAL DUTIES & RESPONSIBILITIES:

Escalation Resolution & Advanced Troubleshooting (≈35%)

• Own the escalation queue: accept complex, high-priority, and urgent tickets escalated from the Level 2 team or generated by automation exceptions, and resolve them within service level commitments
• Perform structured root cause analysis across identity, endpoint, server, network, cloud, and application layers; correct the underlying condition rather than the presenting symptom
• Diagnose and resolve failed or unexpected automation outcomes, restore the affected environment, and document the failure mode for Automation Engineering
• Lead the technical response to client-impacting outages and coordinates with the Security Operations Center for security incidents, following documented incident response procedures
• Communicate clearly and professionally with client stakeholders, including leadership, throughout high-impact incidents, setting expectations and providing accurate status until resolution
• Recognize when an escalation requires vendor engagement, Automation Engineering, or the Director of Engineering, and escalate without delay
• Participate in the support desk phone call queue when Level 1 and Level 2 engineers are in calls

Project Delivery & Infrastructure Engineering (≈30%)

• Deliver client technology projects, managing schedule, risk, and stakeholder communication from kickoff through closeout
• Design, deploy, and maintain physical and virtual servers, storage, and backup and continuity platforms across client environments
• Configure and maintain firewalls, switching, wireless, VPN, and secure remote access in accordance with OSIbeyond security standards
• Administer and architect Microsoft 365, Entra ID, Intune, and Azure environments, including conditional access, single sign-on and identity federation, SharePoint and Teams governance, and hybrid identity
• Plan and execute tenant, mail, file, and server migrations, including discovery, cutover planning, execution, and post-migration validation; prepare detailed, step-by-step directions that peers can execute reliably
• Plan and deliver client-facing technology training and knowledge transfer related to completed projects
• Complete internal projects and scheduled maintenance that support OSIbeyond’s own infrastructure and operations, applying firmware, patching, and configuration changes under appropriate change control
• Contribute to system and network architecture designs, hardware and licensing recommendations, and client technology roadmaps

Automation & AI Enablement (≈20%)

• Analyze escalation, ticket, and project patterns to identify work that should be automated, and author clear, testable specifications for new or expanded automation workflows
• Convert resolved escalations and repeatable project tasks into automation-ready standard operating procedures, decision logic, and knowledge base content that AI and automation can act upon
• Review automation exception logs, tune thresholds and guardrails, and recommend self-healing or preventive detection where recurring failures are observed
• Develop and maintain PowerShell, Microsoft Graph, and KQL scripts and queries that extend the automation platform, standardize project execution, and accelerate investigation
• Apply OSIbeyond-approved AI assistants to diagnostics, ticket history searches, scripting, project planning, and documentation, verifying all AI-assisted output before it is acted upon or delivered

Technical Leadership & Mentorship (≈15%)

• Provide technical direction to peers assigned to project tasks, reviewing their work for quality and completeness
• Mentor Level 2 engineers through escalation walk-throughs, shadowing, and structured feedback that builds their diagnostic depth and reduces future escalations
• Perform peer review of complex changes, migration plans, and client-facing technical documentation prepared by the team
• Maintain and improve the technical knowledge base, standard operating procedures, and client environment documentation so that they remain accurate, complete, and actionable
• Participate in the escalation on-call rotation and serve as the senior technical point of contact during assigned periods
• Contribute to technical training, engineering standards, and continuous improvement initiatives across Technical Services

General Responsibilities

• Provide high-quality written and verbal customer service in every client interaction
• Meet all key performance indicators and notify the Director of Engineering promptly when workload or circumstances place a KPI or project milestone at risk
• Accurately track and document all work in the ticketing and project systems with detail sufficient for a peer to resume the work without additional context
• Set up and support physical hardware through the use of local “smart hands” OSIbeyond engineers
• Support peers and contribute to a collaborative, accountable team culture
• Perform other duties as assigned

SUCCESS METRICS:

• Escalation resolution time and KPI adherence across all assigned tickets
• Root cause quality: escalations closed with documented cause and corrective action, measured by recurrence rate
• Project delivery against agreed scope, schedule, budget, and quality standards, including client sign-off and post-project satisfaction
• Quality and reliability of implementation plans and peer directions, measured by execution errors and rework on project tasks
• Automation contribution: specifications submitted, workflows validated, and automation adopted into production, with the resulting reduction in human-handled tickets and manual project steps
• Automation exception resolution time and accuracy of exception analysis
• Health and currency of internal OSIbeyond infrastructure, including completion of scheduled maintenance
• Client satisfaction with incident handling, project delivery, training, and technical communication
• Mentorship impact: measurable improvement in Level 2 resolution rates for previously escalated issue types
• Documentation quality and completeness of ticket notes, root cause analyses, project records, procedures, and client environment documentation
• On-call responsiveness and resolution quality during assigned rotation periods

SECURITY RESPONSIBILITIES:

• Complete training for and maintain awareness of cybersecurity risks, including insider threat, and the appropriate handling of CUI and other regulated data
• Treat client data and OSIbeyond data as sensitive, and do not disclose, release, or otherwise transfer it outside of OSIbeyond or client environments without written permission
• Follow cybersecurity requirements as described in the Employee Handbook and other OSIbeyond policies
• Immediately follow incident response procedures when a security incident or concern is identified
• Design and implement client and internal infrastructure in accordance with OSIbeyond security baselines and applicable client compliance requirements, including CMMC and NIST SP 800-171
• Assist with the escorting or monitoring of visitors when working onsite

QUALIFICATIONS

Experience

• Four or more years of progressive experience in systems engineering, infrastructure administration, or escalation support, with the most senior engineers in the position typically bringing seven or more; managed service provider experience is strongly preferred
• Demonstrated ownership of complex, multi-layer escalations and client-impacting incidents through to root cause and resolution
• Hands-on delivery of infrastructure projects such as server deployments, firewall implementations, identity architecture, or tenant and data migrations; experience scoping and leading such projects end to end is expected at the senior end of the position

Infrastructure & Platform Skills

• Expert administration of Microsoft 365 and Entra ID, including Exchange Online, SharePoint Online, Teams, conditional access, identity federation and single sign-on, and audit logging
• Strong Windows Server, Active Directory, Group Policy, DNS, DHCP, and NTFS and DFS permission design; working knowledge of hybrid identity synchronization
• Virtualization and storage administration (Hyper-V or VMware), and backup and business continuity platforms
• Firewall, switching, wireless, VPN, and routing configuration and troubleshooting; solid grounding in TCP/IP, DNS, and network security
• Microsoft Azure and Intune administration, including virtual machines, networking, device management, and compliance policies
• Email security and spam filter administration, and security incident response in coordination with a SOC

Project & Automation Skills

• Ability to produce a project implementation plan and cutover schedule, manage risk and stakeholder communication, and close out with validation and training
• Ability to write detailed, unambiguous technical directions that peers can execute without supervision
• Proficiency in PowerShell and Microsoft Graph; working knowledge of KQL or comparable query languages
• Ability to decompose a resolved escalation or repeatable project task into decision logic, parameters, and guardrails suitable for automation
• Experience validating or troubleshooting the output of automation and orchestration platforms (Tines or comparable), RMM scripting, or infrastructure-as-code
• Effective, verified use of AI assistants for diagnostics, scripting, planning, and documentation

Professional Skills

• Composed, authoritative communication with client stakeholders and leadership during high-impact incidents and project cutovers
• Disciplined documentation and ticket hygiene; ability to produce clear technical writing and deliver training for both engineers and non-technical audiences
• Demonstrated ability to mentor, direct, and raise the capability of less experienced engineers
• Self-management appropriate to a remote, escalation- and project-driven role with on-call responsibilities

Additional Desirable Qualifications

• Experience supporting clients subject to CMMC, NIST SP 800-171, or similar regulatory frameworks
• Prior contribution to automation development, detection engineering, or platform standardization in an MSP environment
• Formal project management training or certification (CompTIA Project+, PMP, or equivalent)
• Experience with Azure landing zones, infrastructure-as-code, or zero trust network architecture

KNOWLEDGE & CERTIFICATIONS

Tooling Environment: Microsoft 365, Entra ID, Intune, and Azure administration portals; Windows Server and hypervisor management; firewall and network management platforms; remote monitoring and management; backup and continuity platforms; Tines automation; Autotask professional services automation (ticketing and projects); IT documentation platform; Microsoft Teams for internal collaboration; OSIbeyond-approved AI assistants.

Required Certifications (or attainment within the first six months)

• Microsoft MS-102: Microsoft 365 Administrator
• Microsoft AZ-104: Microsoft Azure Administrator

Preferred Certifications

• Microsoft SC-300: Identity and Access Administrator
• Microsoft MD-102: Endpoint Administrator
• CompTIA Security+ or CompTIA Network+
• Vendor firewall certification (Fortinet NSE, Palo Alto PCNSA, or equivalent)
• CompTIA Project+ or PMP

Position:

• Location - Remote from the United States, must be willing to work EST hours
• Employment Type - Full time

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.