Team Lead - Microsoft Systems Architecture, Managed Services

The Team Lead, Proactive Engineering is responsible for assisting in the leadership, planning, and execution of proactive engineering initiatives across client environments. This role focuses on driving continuous service improvement, optimizing platform health, and preventing incidents before they occur.

Operating within Managed Services standards and SLAs, this role specializes in Digital Workspace technologies, including operating systems, Microsoft 365, endpoint management, applications, and VDI platforms. The Team Lead collaborates with engineering, operations, and client stakeholders to develop proactive strategies, enforce standards, and elevate overall service maturity.

This individual will guide a team of engineers focused on proactive, non-reactive work, ensuring consistent delivery of preventive maintenance, optimization, automation, and client value-driven initiatives., Strategy & Planning

• Define and execute proactive engineering strategies to improve performance, reliability, and scalability of client network environments.
• Develop and maintain standards, policies, procedures, and playbooks focused on preventative maintenance and continuous improvement.
• Establish best practices for Microsoft 365, endpoint management, operating systems, VDI, and enterprise applications.
• Develop methodologies for measuring environment health including patch compliance, device health, and identity posture.
• Partner with leadership to evolve Managed Services toward a proactive-first delivery model.
• Identify automation opportunities and implement repeatable solutions to improve efficiency.
• Collaborate with leadership on Managed Services SLAs, escalation paths, and process maturity (incident/problem/change management).
• Drive client loyalty and long-term value by improving client retention rates through consistent delivery of proactive engineering outcomes and measurable service improvements.
• Increase overall client satisfaction by positively impacting NPS scores and survey feedback through improved system stability, communication, and visible value delivery.
• Drive revenue growth by identifying and delivering strategic recommendations that align technology improvements to client business objectives and future roadmaps.

Acquisition & Deployment

• Plan and coordinate proactive improvements and enhancements across client environments.
• Conduct research and recommend tools and technologies supporting proactive engineering.
• Evaluate monitoring, reporting, and automation platforms to enhance system visibility.
• Ensure all initiatives follow Managed Services change management processes.

Operational Management

• Lead and coordinate a team focused on preventative maintenance, optimization, and service improvement.
• Oversee proactive services including patching, performance tuning, identity optimization, and VDI improvements.
• Drive root cause elimination through trend analysis and long-term remediation.
• Collaborate with reactive teams to convert recurring issues into proactive initiatives.
• Maintain communication with stakeholders regarding environment health and improvements.
• Ensure consistency in documentation and process maturity.
• Provide leadership, mentorship, and technical guidance.

Do you have experience in Windows?, Do you have a Bachelor’s degree?, Four-year degree in Computer Science or related field and/or equivalent experience.

• Highly desired certifications (or equivalent demonstrated experience):
• Microsoft 365 Certified: Administrator Expert (MS-102)
• Microsoft: Identity & Access / Security / Teams Administrator / Microsoft 365 (role-based equivalents acceptable)
• ITIL (Managed Services process alignment), * 8+ years supporting Digital Workspace environments.
• Strong expertise in Microsoft 365, Active Directory, and endpoint management.
• Experience with Windows operating systems and VDI platforms.
• Experience designing proactive health and optimization programs.
• Knowledge of automation (e.g., PowerShell).
• Understanding of security best practices including Zero Trust and MFA.
• Advanced working knowledge of Entra ID (Azure AD), including MFA, Conditional Access, SSO, and identity troubleshooting.
• Extensive experience with the Microsoft Active Directory stack including Users & Computers, Group Policy, Site & Services, AD FS, AD CS, DNS, and DHCP.
• Exceptional knowledge in Microsoft Server 2016, 2022, and 2025.
• Working knowledge of Linux (RHEL, Debian, and various spinoffs).
• Hands-on experience of Exchange On-Prem administration.
• Experience integrating workspace services with hybrid/on-prem components (Entra Connect / Cloud Connect) is a plus.
• Strong understanding of modern authentication, device identity, and access models (Zero Trust, OAuth/SAML concepts, federated identity fundamentals).
• Experience developing automation and orchestration relevant to Managed Services operations (e.g., PowerShell, Graph-based administration concepts)., * Demonstrated leadership and team management skills.
• Strong analytical and problem-solving mindset focused on prevention.
• Excellent communication skills.
• Ability to prioritize work in a fast-paced environment.
• Strong ownership, accountability, and documentation discipline.
• Ability to explain technical concepts in user-friendly language to both technical and non-technical stakeholders.
• Ability to work independently and/or in a group to meet Client expectations.
• Demonstrates ownership and accountability for systems, projects, and outcomes.
• Comfortable working cross-functionally with security, networking, infrastructure, and leadership teams.

Work Conditions

• Sitting for extended periods.
• Dexterity to operate computer equipment.
• Travel to client sites (>20%)