Job Description

Job Title: IT Director

Location: Chicago, IL | Travel Required (up to 40%)

Reports To: Chief Strategy Officer

Position Summary

The IT Director will be the first hire dedicated to building and leading the IT function. This is a hands-on, high-impact leadership role responsible for developing the IT strategy, building out scalable infrastructure, and supporting newly acquired agencies through integration. The ideal candidate will have both strategic vision and the ability to execute across hardware, software, security, and support. As we grow, were building a future-ready technology foundationand were looking for an IT leader to drive it.

Key Responsibilities

Technology Leadership

• Design and implement a scalable IT roadmap aligned with business growth.
• Serve as the company-wide IT expert and advisor for executives, operations, and newly acquired agencies. First responder to IT related issues.
• Establish IT governance, policies, and best practices across the organization.

Acquisition Integration

• Build and lead onboarding newly acquired agencies into the company's IT ecosystem.
• Travel to acquired agencies to conduct IT assessments, inventory audits, and network reviews.
• Recommend, implement, and manage hardware/software standardization during integrations.

Operations & Infrastructure

• Manage all company-wide IT infrastructure: networks, hardware, software, and cloud services.
• Lead the evaluation and procurement of technology systems and equipment.
• Oversee corporate file systems and shared drives to ensure security, accessibility, and standardization.

Team Development

• Build and manage an internal IT team as growth dictates (support, infrastructure, security, etc.).
• Establish KPIs and operational metrics to ensure IT performance and user satisfaction.

Vendor & Inventory Management

• Manage relationships with external IT service providers and technology vendors.
• Oversee hardware procurement, deployment, tracking, and company-wide inventory management.

Requirements

Experience

• 7+ years of progressive experience in IT, including leadership roles.
• Degree in Computer Science or related field.
• Prior experience supporting M&A or working in a multi-location organization is highly preferred.
• Experience managing both infrastructure and end-user systems in a hybrid environment.

Skills

• Strong project management and vendor negotiation skills.
• Excellent interpersonal skills, with the ability to explain technical concepts to non-technical stakeholders.
• Proficiency with Microsoft 365, Windows Server environments, cloud systems (Azure, AWS), and cybersecurity frameworks.
• Understanding of compliance requirements related to data protection and insurance (preferred).

Attributes

• Strategic thinker with a builder mindset.
• Willingness to travel regularly to agency locations.
• Strong leadership presence with a collaborative approach to change management.
• Competitive salary and benefits package.

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