IT Director

About Us

Position Summary

Scope of the Role

• People Supported: About 850 people across the organization.
• Offices: 41 offices, each fronted by its own firewall.
• Wireless & Switching Sites: 36 of those offices with local switching and wireless on site, covering 33 switches and 63 access points.
• Servers:  About a dozen Windows servers on two hypervisors at two sites, plus two domain controllers and a Remote Desktop farm.
• Team: Two IT technicians as direct reports. MSP
• Regions: Six U.S. regions, plus Canada, plus two acquired companies that currently keep their own systems.

Key Responsibilities

• IT Operations: Manage day-to-day IT operations, including network, server, endpoint, and cloud infrastructure across all Affinity Group offices.
• Support & Help Desk: Lead and prioritize the IT help desk function, ensuring timely resolution of employee support requests and tracking recurring issues.
• Systems Administration: Administer core business systems and platforms (e.g., Microsoft 365, CRM, and other line-of-business applications), coordinating upgrades, integrations, and access management.
• Security & Compliance: Implement and maintain data security, backup, and disaster recovery practices; monitor for vulnerabilities and coordinate remediation.
• Vendor & Third-Party Risk: Manage relationships with IT vendors, the managed service provider, and telecom/internet carriers, including contract renewals, performance, and assessment of third-party security and business risk.
• Budget & Planning: Plan and track the IT budget, evaluate new tools and equipment purchases, and recommend cost-effective solutions.
• Projects: Lead technology rollouts (new hardware, software, or office setups) from planning through deployment and training.
• AI Governance: Own governance of AI-assisted tools and automation used within IT, ensuring their use follows Affinity Group's AI and development policies and gets appropriate review.
• Strategy & Growth: Partner with senior leadership on the IT roadmap and budget as the business grows, including evaluating what stays in-house versus with outside partners.
• Cross-Team Collaboration: Partner with Sales, Marketing, and Operations leaders across both divisions to understand technology needs and support regional teams.
• Documentation & Training: Maintain documentation for systems, processes, and IT policies, and train employees on tools and security best practices.

Required Qualifications

• Bachelor’s degree in information technology, Computer Science, or a related field, or equivalent hands-on experience.
• Prior experience managing IT operations, systems administration, or a help desk/support function.

• Microsoft 365 and Microsoft Entra ID administration, including Exchange Online, SharePoint, Teams, and licensing.
• Microsoft Intune and Windows endpoint management.
• Windows Server, Active Directory, Group Policy, Hyper-V, and Remote Desktop Services.
• Backup and recovery, and infrastructure monitoring.
• Business network administration across many small offices, including Cisco Meraki firewalls, Aruba Instant On switching and wireless, and domain name service.
• Endpoint and email security, multi-factor authentication, and a password vault.
• Microsoft Azure at a small-business scale, including scheduled automation and secret storage.
• IT service management in a help desk platform, including assets, change, and a knowledge base.
• PowerShell scripting, source control, and AI-assisted automation.
• Vendor and license management for hardware, software, and telecommunications.
• Strong written and verbal communication, with the ability to explain technical topics to non-technical staff.
• Proactive, detail-oriented, and comfortable managing multiple priorities across a distributed, multi-office organization.

• Microsoft certifications relevant to this environment (e.g., Microsoft 365 Certified: Administrator Expert, Azure Administrator Associate, or Security Operations Analyst Associate).
• ITIL Foundation, for IT service management practice.
• PMP or a similar project management certification.
• A security certification such as CompTIA Security+ or (ISC)² SSCP/CISSP.

What to Expect

• Full-time schedule; hybrid work arrangement with in-office days at the assigned location.
• Availability for occasional after-hours or on-call support for critical system issues.
• Some travel to regional offices may be required.
• Prolonged computer work.

Benefits

• Medical, dental, and vision coverage.
• 401(k) retirement plan.
• Paid time off and company holidays.

Equal Opportunity Statement

The Affinity Group is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. All employment is decided on the basis of qualifications, merit, and business need.