Roundstone

Position: IT Operations Manager

Founded in 2003, Roundstone is not your typical insurance company. We’re on a mission to help employers save on healthcare benefits so they can put those savings towards bettering their businesses and taking care of their employees.

We are seeking an experienced IT Operations Manager to oversee the daily operations of our growing IT department. As part of the technology leadership team, you will ensure the performance, reliability, and security of IT systems while aligning technology services with the company’s strategic objectives. You will lead a diverse technical team, including system administrators and help desk personnel, serving as both a technical expert and people manager. This hands-on role requires a senior-level technician with a customer service background and the ability to serve as the final escalation point for IT support.

IT Operations & Infrastructure Management

• Oversee daily operations of IT infrastructure, including servers, networks, cloud platforms, and applications.
• Manage and maintain Active Directory (user provisioning, group policy management, access controls).
• Ensure performance, security, and reliability of IT systems and infrastructure.
• Manage hardware/software installation, configuration, and upgrades.
• Maintain data backup and disaster recovery strategies.
• Analyze business workflows to identify opportunities for technology improvements.
• Align IT systems, tools, and strategies (including AI and Power Automate) with business goals to drive efficiency.

Team Leadership & Service Management

• Lead, mentor, and manage IT staff, including system administrators and help desk personnel.
• Promote a professional work ethic, coach staff, and support career development.
• Ensure timely IT support by managing ticketing systems and enforcing SLAs.
• Conduct performance evaluations and drive continuous improvement within the team.

Help Desk & End-User Support

• Serve as the senior escalation point for complex IT issues (hardware, OS, software).
• Oversee the help desk team, support queue, and remote support tools to ensure efficient operations and deliver outstanding customer service
• Provide advanced support for Windows 10/11, Microsoft Intune, and Autopilot provisioning.
• Troubleshoot user access, compliance, and conditional access issues.
• Maintain documentation and internal knowledge base for IT support.

IT Strategy & Project Management

• Plan, execute, and oversee IT projects (infrastructure upgrades, system migrations).
• Evaluate and implement new technologies to enhance IT operations.
• Collaborate with other departments to align IT services with organizational goals.
• Ensure compliance with industry standards and internal policies.

Security, Monitoring & Compliance

• Identify and remediate security vulnerabilities to ensure data protection.
• Maintain security tools (e.g., Palo Alto Networks, Zscaler, Sentinel One).
• Perform regular audits to ensure IT compliance.
• Collaborate with security leaders to ensure a secure IT environment.

Technical Expertise

• 7+ years of experience in IT support or infrastructure roles.
• Expertise in Active Directory administration (user/group management, GPOs, permissions).
• Proficiency with Microsoft Azure, Hyper-V, and Intune.
• Experience with Windows environments, imaging, patching, and automation (e.g., PowerShell).
• Familiarity with security tools like Zscaler, SentinelOne, Palo Alto.
• Hands-on experience with ITSM platforms and help desk ticketing systems.
• Strong knowledge of Microsoft 365, SharePoint, OneDrive.
• Experience with Power Automate and AI tools to automate business processes.

Leadership & Communication

• Proven ability to manage, mentor, and develop IT teams and help desk staff.
• Excellent verbal and written communication skills.
• Ability to explain complex issues to non-technical stakeholders.
• Customer-focused with strong problem-solving abilities.

Strategic & Analytical Thinking

• Strong business acumen with the ability to align IT solutions with company objectives.
• Analytical and organizational skills for managing multiple priorities in a fast-paced environment.

We’re leaders in our industry, so naturally, we look out for our employees’ best interests with a robust benefits package. Roundstone employees are eligible for:

Headquartered in Rocky River, Ohio, Roundstone is regularly recognized as a Northeast Ohio Top Workplace by the Plain Dealer and cleveland.com. We are especially proud to be recognized as a Top Workplace since this honor is determined by anonymous feedback from our own employees. Roundstone employees enjoy a supportive workplace where they are engaged, valued and regularly recognized for their hard work at monthly company meetings. Roundstone’s core values are evident every day and are shared with the community through the sponsorship of community events and outreach.

Culture and fit are integral to success and in an effort to achieve a better match both from a candidate's perspective and our organization, please take a minute, click on the link and take the really brief survey: https://go.cultureindex.com/p/tVgnOQTBTysiBQS

Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Roundstone Insurance we are dedicated to building a diverse, inclusive, and authentic workplace, so if you're excited about this role but your past experience doesn't align perfectly with every qualification in the job description, we encourage you to apply anyways. You may be just the right candidate for this or other roles.