Senior IT Technician (Microsoft 365 Admin)

Job Title: Senior IT Technician (Microsoft 365 Admin)

Company: Topsail Re Underwriters LLC

Location: Hoffman Estates, IL

About Topsail Re:

Topsail Re is a closely held total return Reinsurer domiciled in the Cayman Islands with affiliated offices in Greensboro, NC and Hoffman Estates, Illinois. Our strategy is to be disciplined and patiently develop long-term profitable relationships with companies that are like minded. Topsail Re will not be purely opportunistic but rather seek out business partners that fit our long-term view of underwriting and in turn create a true value proposition for all parties.

Salary Range: $55,000 - $104,000 per year (based on experience and qualifications)

Benefits:

Topsail Re Underwriters LLC is proud to offer the following benefits: medical insurance (generously covering a large portion of the premium for employees and their families), comprehensive dental and vision insurance, long-term disability insurance and group-term life insurance, substantial employer-funded contributions for health savings accounts (HSAs), employer-matching contributions for 401(k) plan, and paid time off (PTO).

Job Summary:

We are seeking an experienced and highly skilled Senior IT Technician reporting to Topsail's IT Director, with comprehensive expertise in Microsoft 365 administration. In this role, you will lead IT projects, provide technical support, and optimize Microsoft 365 environments to enhance productivity and ensure seamless operations. Your ability to troubleshoot complex technical issues and implement innovative solutions will be pivotal to the success of our IT infrastructure.

Key Responsibilities:

• Administer and manage Microsoft 365 services, including Exchange Online, Teams, SharePoint, OneDrive, and Azure AD.
• Oversee the deployment, configuration, and maintenance of Microsoft 365 applications and features.
• Implement security best practices for Microsoft 365, including data loss prevention, multifactor authentication, and device management.
• Manage user accounts, licenses, permissions, and policies within the Microsoft 365 environment.
• Monitor and resolve issues related to email systems, collaboration tools, and other Microsoft 365 services.
• Lead IT projects, such as migrations to system upgrades and integrations.
• Provide advanced technical support to end users, ensuring prompt resolution of IT issues.
• Collaborate with cross-functional teams to identify IT needs and develop tailored solutions.
• Maintain documentation for system configurations, processes, and troubleshooting procedures.
• Stay up to date on Microsoft 365 updates and emerging technologies, sharing insights and recommendations with the team.

Qualifications:

• Bachelor’s degree or equivalent experience.
• Proven experience as an IT Technician with specialization in Microsoft 365 administration (3 years preferred).
• Expertise in Microsoft 365 services, including Exchange Online, Teams, SharePoint, OneDrive, and Azure AD.
• Knowledge of IT security protocols and compliance standards.
• Experience with PowerShell scripting for automation and task management.
• Proficiency in networking concepts, cloud-based solutions, and virtualization.
• Excellent problem-solving skills and the ability to manage complex technical challenges.
• Strong communication and interpersonal skills for collaboration and end-user support.
• Relevant certifications (e.g., Microsoft Certified: Modern Desktop Administrator Associate, Microsoft 365 Certified: Enterprise Administrator Expert) are a plus.

How to Apply:

Interested candidates are invited to submit a resume and cover letter outlining their qualifications and explaining why they are suitable for this position. Please apply via LinkedIn or email your application to Joe Ciriano, IT Director at jciriano@topsailre.com.

Topsail Re is an equal opportunity employer. We encourage applications from candidates of all backgrounds and experiences.

Application Deadline: April 30, 2025

Note: Only shortlisted candidates will be contacted for an interview.

Topsail Re Underwriters LLC

2895 Greenspoint Parkway, Suite 625

Hoffman Estates, IL 60169