Director of Desktop Engineering and Microsoft 365 Administration

Job Description:

Penn Mutual Life Insurance Company is seeking an experienced Director of Desktop Engineering and Microsoft 365 Administration to lead and drive the strategy, design, and execution of end-user computing and collaboration technologies. This critical leadership role will oversee desktop engineering, Microsoft 365 administration, and end-user support operations to ensure a secure, efficient, and innovative IT environment.

The ideal candidate will bring a visionary approach to desktop and collaboration technologies, leveraging modern solutions to enhance productivity, security, and user experience. This individual will lead high-performance teams, align technology roadmaps with business objectives, and drive operational excellence in desktop engineering and Microsoft 365 service delivery. Additionally, the role will require strong vendor management experience, particularly in engaging third-party professional services providers for complex systems integration projects.

We seek an individual that will advocate technology adoption, working closely with business stakeholders to identify opportunities to leverage technology for employee productivity and competitive advantage.

We've embraced a flexible, hybrid approach to work. Based on your role and personal preference, we empower you to choose where you work best. This model allows you to balance your life and bring your whole self to work.

Responsibilities

Strategic Leadership & Technology Advocacy

• Develop and execute the strategic roadmap for desktop engineering, Microsoft 365 services, and end-user support
• Collaborate with IT leadership to align end-user computing initiatives with business goals and digital transformation efforts
• Serve as a technology advocate and advisor to business leaders, translating complex technical concepts into business value propositions
• Evaluate emerging technologies and industry trends to continuously improve security, automation, and user experience

Cross-Functional Partnership & Business Alignment

• Partner with business units across the organization to understand their operational challenges and technology requirements, and resolve IT operational issues
• Lead cross-functional initiatives that leverage desktop and collaboration technologies to drive business process improvements

Technical Leadership & Operations

• Lead the design, deployment, and optimization of enterprise-wide desktop environments, including Windows OS, MacOS, endpoint management (e.g., Intune, Ivanti), software deployment
• Drive the administration and governance of Microsoft 365 services, ensuring security, compliance, and efficiency across Exchange Online, SharePoint Online, OneDrive, Conditional Access, and authentication services
• Oversee the development of automation and scripting solutions (e.g., PowerShell) to streamline IT operations and improve efficiency
• Champion a zero-trust security model and enforce best practices in endpoint security, data protection, and identity management
• Lead complex systems integration efforts, ensuring seamless interoperability between desktop platforms, collaboration tools, and enterprise applications

Team Leadership & Organizational Development

• Lead teams of Desktop Engineers, Microsoft 365 Administrators, and Help Desk professionals, fostering a culture of innovation and accountability
• Develop and manage budgets, resource allocation, and project timelines for IT initiatives
• Build strong relationships with internal customers and external vendors to ensure effective service delivery

Skills and Abilities

Technical Expertise

• Proven expertise in Microsoft 365 administration, including Exchange Online, SharePoint Online, Conditional Access, MFA, and endpoint security
• Strong technical knowledge of Windows OS, MacOS, endpoint management tools (e.g., Intune, Ivanti), and software deployment strategies
• Experience with security frameworks (e.g., NIST, ISO 27001) and compliance standards related to desktop and cloud environments
• Knowledge of automation and scripting (e.g., PowerShell, Ansible, Terraform, etc.) preferred
• Familiarity with ITIL or other IT service management frameworks preferred

Leadership & Business Acumen

• Demonstrated experience engaging and managing third-party professional services firms for complex systems integration, cloud migrations, and enterprise IT modernization projects
• Exceptional leadership and communication skills, with a track record of building and leading high-performing IT teams
• Experience collaborating across