Senior Project Engineer (Tier 3)

Role Summary

The Senior Project Engineer (Tier 3) is a highly experienced individual contributor responsible for delivering complex technical projects, serving as a top-tier escalation point, and providing deep technical mentorship to the engineering team.

Primary Duties

• Project Execution:
• Execute defined scopes of work with minimal oversight, ensuring technical accuracy, security alignment, and documented results.
• Collaborate with Project Managers and/or the Director of Service Operations to provide accurate estimates, identify technical risks, and deliver tasks on time.
• Provide status updates on assigned project tasks and collaborate closely with Project Managers, Engineers, and Service Managers.
• Identify risks or blockers during project execution and escalate appropriately.
• Own complex project workstreams such as cloud migrations, advanced networking/security deployments, M365/Azure transformations, and Intune/Autopilot rollouts.
• Provide accurate and timely technical documentation, implementation plans, and client-facing deliverables.
• Participate in the technical project process from kickoff through completion, ensuring all milestones, scope, and deadlines are met.
• Coordinate with other project resources (Tier 1 and Tier 2 engineers, support staff, vendors, etc.).
• Ensure all project documentation, testing, and client communications are accurate and complete.
• Escalation & Mentorship:
• Serve as the final escalation point for high-priority or unresolved issues passed up from Tier 1 and Tier 2 engineers.
• Actively coach and upskill Tier 1 and Tier 2 engineers through side-by-side troubleshooting, knowledge-sharing, and technical walkthroughs as the opportunity presents itself.
• Develop troubleshooting guides and documentation to reduce repeat escalations.
• Solutions Architecture:
• Architect solutions as assigned by the Project Manager. Ensuring scalability, security, and alignment with client business goals.
• Contribute to the development and enforcement of Proper Sky’s best practices, security baselines, and compliance frameworks (CIS v8, NIST, HIPAA, etc.).

Qualifications

• Education & Technical Experience:
• 7+ years of relevant hands-on IT support experience in a helpdesk, MSP, or technical support environment.
• Microsoft Cloud & Azure Expertise - Advanced, hands-on administration of Microsoft 365 and Azure, including Azure AD, hybrid identity, Azure IaaS/PaaS, security tooling, and tenant-level architecture decisions.
• Endpoint Management – Deep, real-world experience with Intune and Autopilot, including device provisioning, compliance policies, conditional access integration, and zero-touch deployment at scale.
• Networking & Security – Strong enterprise networking (routing, switching, VLANs, firewalls, VPN/SD-WAN), with applied knowledge of frameworks (CIS, NIST, HIPAA) and tools (EDR, SIEM).
• Certifications (Preferred, not required): Microsoft Azure Solutions Architect Expert, Microsoft 365 Security Administrator, Endpoint Administrator (Intune/Autopilot). Advanced networking or security certifications (CCNP, CISSP, CISM, PMP) are a plus.
• Administrator, Endpoint Administrator (Intune/Autopilot), plus advanced networking/security (CCNP or similar) (CISSP, CISM, PMP preferred).
• Familiarity with backup systems, EDR platforms, and RMM tools
• Experience with ConnectWise Manage, Automate, ScreenConnect, or similar tools preferred
• Soft Skills:
• Strong verbal and written communication skills
• Ability to manage multiple tasks and prioritize in a fast-paced environment
• Self-starter with a continuous learning mindset
• Team player with mentoring capabilities
• Hightly organized, detail-oriented, and customer-service driven

Work Schedule

The Support Technician role covers the 8am-5pm EST shift. The position is subject to covering a rotating “On-Call” shift from 5pm-10pm (Weekdays) and 8am-5pm (Weekends/Holidays) to respond to after-hours emergency requests.

Work Location

This role is a hybrid role and reports locally to Proper Sky’s headquarters in Abington, PA for all scheduled shifts.