Senior Project Engineer

Why Work for Proper Sky?

At Proper Sky, your work will make an impact from day one. As a small and agile team, we offer meaningful responsibility early on and continuous opportunities to grow, no matter your role. Every day brings fresh challenges and the chance to build new skills in a collaborative, fast-paced environment.

You’ll work closely with leadership and key stakeholders, gaining visibility and influence across the organization. Our team is made up of dedicated, mission-driven professionals who care deeply about delivering exceptional results for our clients and supporting one another.

We’re committed to your development and success. We provide leadership and professional growth opportunities through industry-leading programs like IT Nation, along with other third-party training and support. At Proper Sky, you’ll learn our systems, improve them, and bring value every day.

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. This role is not responsible for overall project management, but collaborates closely with Project Managers, vCIOs, and Service Managers to ensure successful implementation of scopes of work. The Senior Project Engineer excels at hands-on execution, resolving escalated issues, and driving technical standards that align with Proper Sky’s service excellence, cybersecurity-first approach, and client mission objectives.

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
• Highly 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.

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