IT Director

Job Summary

The Director of Information Technology will serve as the senior technology leader for our growing, multi-site, multi-region organization. This is a strategic yet hands-on role for a leader who can define the direction of our technology function and personally drive execution — building and operating a lean, high-performance IT function largely through managed vendors and partners. The Director will report to the Chief Financial Officer and will be a key contributor to our growth strategy, particularly as we continue to acquire and integrate new operating locations, automate KPI and data workflows, and mature our cybersecurity posture. We are not building a large IT department; we need a leader who rolls up their sleeves.

Key Responsibilities

Strategy & Leadership

• Define and execute a multi-year IT roadmap aligned to business growth, acquisition activity, and operational efficiency goals
• Serve as the primary technology advisor to the senior leadership teamfor new initiatives like AI
• Establish IT governance frameworks, policies, and standards across all operating locations
• Build and manage a lean IT function primarily through strategic vendor and MSP relationships
• Lead annual IT budgeting, forecasting, and ROI analysis on technology investments

Data, Automation & KPI Production

• Lead initiatives to automate KPI reporting and operational dashboards, reducing manual data handling and accelerating business insight
• Partner with operations, finance, and HR to define data standards, sources of truth, and reporting hierarchies across business units
• Oversee integration architecture between core platforms: Acumatica, Aspire (ServiceTitan), ADP Workforce Now, HubSpot, and Microsoft 365/Azure
• Drive data quality, governance, and accessibility practices that support leadership decision-making
• Evaluate and implement AI and automation tools that create operating leverage across the business

Infrastructure & Systems Management

• Maintain and continuously improve our Microsoft 365 and Azure environment, including identity management, security policies, and licensing optimization
• Oversee multi-site network infrastructure: internet connectivity, managed switches, Wi-Fi, cameraand securitysystems, and physical hardware
• Manage hardware lifecycle (laptops, tablets, mobile devices, printers, scanners) across all locations
• Assistwith all production software optimization including Aspire (ServiceTitan), Acumatica, ADP Workforce Now, HubSpot and other production apps
• Coordinate technical elements of field operations technology: vehicle GPS systems, automated equipment, and related R&D initiatives

M&A Integration, Cybersecurity & Vendor Management

• Lead IT due diligence and integration planning for new company acquisitions; travel toacquiredlocations duringinitialconversion activities
• Drive technology standardization across all operating entities,eliminatinglegacy fragmentation
• Own the company’s cybersecurity strategy: threat monitoring, incident response, endpoint protection, access controls, and security awareness training
• Establish andmaintaindisaster recovery and business continuity plans; ensure compliance with applicable data security standards
• Select, contract, and manage all third-party IT service providers, MSPs, and technology consultants; define and enforce SLAs

User Support & Enablement

• Ensure high-quality, responsive IT support for all employees across locations via direct effort and/or vendors
• Partner with HR on building robust onboarding and offboarding procedures for IT
• Deliver end-user training and communicate clearly with staff at varying levels of technical understanding

Job Skills and Personal Characteristics

• Strategic thinker who is equally comfortable in execution — a leader who rolls up their sleeves
• Excellent communication and patience working with and training non-technical users
• Team player comfortable with a fast-paced working environment managing multiple priorities
• Highly organized, self-motivated, and capable of working both independently and collaboratively

Position Requirements

• Bachelor’s degree in Information Technology, Computer Science, or a related field; equivalent experience considered
• 8+ years of progressive IT experienceanddemonstratedsuccess as adirector, senior manager, or equivalent leadership role
• Demonstrated experience managing IT in a multi-site, field-operations, or distributed organization
• Deepexpertisein Microsoft 365 administration, Azure AD / Entra ID, and cloud infrastructure
• Hands-on experience with ERP, CRM, and HRIS integrations (Acumatica,ServiceTitan/Aspire, ADP, or HubSpot preferred)
• Proven ability to manage a vendor and MSP ecosystem as the primary delivery model
• Experience leading technology integrations in an M&A or multi-entity growth context
• Strong cybersecurity knowledge including endpoint protection, identity management, and incident response
• Experience building KPI dashboards, data pipelines, or BI environments (Power BI, Dataverse, or similar) preferred
• Relevant certifications preferred: Microsoft (MS-102, AZ-104), CISSP, CISM, PMP, or equivalent
• Valid driver’s license with acceptable driving record to meet fleet insurance standards
• Must be able to pass a drug and alcohol test

Work Conditions

This position requires regular travel to present and future operating locations and must offer flexibility with work hours outside of regular business hours to meet internal client needs. The Director should expect to spend time on site at acquired or newly converted locations during integration activities. This position may require working from various locations or from home, as needed.