IT Director

Description Overview John C. Cassidy Air Conditioning & Plumbing is seeking a driven, hands-on technology professional to help build and lead the next stage of our IT organization. This is a growth opportunity designed for someone ready to move into a Director-level role and build an IT department from the ground up. The ideal candidate is a strong technical operator who wants more ownership, executive exposure, and the opportunity to shape how technology supports a rapidly growing organization.

This will be a hands-on role from day one . Initially, the IT Director will operate as an individual contributor, personally managing technology infrastructure, cybersecurity, enterprise applications, user support, vendors, and technology projects across multiple HVAC, plumbing, and home-service brands. As the organization grows, this individual will have the opportunity to build the IT function, establish processes and standards, and ultimately develop and lead an internal IT team.

We are looking for someone who is equally comfortable developing a technology roadmap with executive leadership and rolling up their sleeves to troubleshoot an issue, configure a system, manage an implementation, or support an end user. What You’ll Do Serve as the company's primary technology leader and advisor to executive leadership.

Develop and execute a scalable technology roadmap aligned with business growth and operational needs. Personally manage the day-to-day IT environment while building the foundation for a future internal IT department. Manage Microsoft 365, Azure, Active Directory, networking, telecommunications, endpoints, servers, and cloud infrastructure.

Own cybersecurity initiatives, including MFA, endpoint protection, vulnerability management, security policies, incident response, audits, and cyber insurance requirements. Maintain backup, disaster recovery, and business continuity processes. Administer and support enterprise applications, including Service. Titan, Microsoft 365, ERP, CRM, HRIS, accounting, and business intelligence platforms.

Lead technology implementations, upgrades, integrations, migrations, and user adoption initiatives. Identify opportunities to improve workflows through technology, integration, and automation. Establish data governance and Master Data Management standards to improve data quality and reporting. Help build a scalable data environment capable of supporting dashboards, automation, analytics, and future AI initiatives.

Provide and coordinate day-to-day technology support across company locations. Maintain IT documentation, asset inventories, policies, licensing, and standard operating procedures. Manage MSPs, technology vendors, telecommunications providers, contracts, and other external partners. Support technology integration and planning associated with acquisitions and new locations.

Evaluate opportunities to bring technology capabilities in-house as the organization grows. Build the structure, processes, and roadmap for a future internal IT team. What We’re Looking For Progressive experience in IT, infrastructure, systems administration, technology operations, or a related area. Strong hands-on experience with Microsoft 365, Azure, Active Directory, networking, cloud technologies, and enterprise infrastructure .

Experience supporting users and technology across multiple locations. Strong understanding of cybersecurity practices, endpoint management, access controls, backups, and disaster recovery. Experience implementing or administering enterprise business applications such as ERP, CRM, HRIS, accounting, or field-service platforms.

Experience leading technology projects and working directly with third-party vendors or MSPs. Ability to troubleshoot technical issues and personally execute solutions rather than relying solely on outside resources. Strong communication skills with the ability to work effectively with executives, operational leaders, vendors, and end users.

Ability to balance long-term technology strategy with immediate, hands-on operational needs. Strong organizational, analytical, and problem-solving skills. Bachelor's degree in Information Technology, Computer Science, Information Systems, or a related field preferred.

Preferred Qualifications

Experience with Service. Titan or another field-service management platform. Experience in HVAC, plumbing, construction, home services, manufacturing, or another multi-location field-service environment. Experience supporting mergers, acquisitions, or technology integrations. Experience with Microsoft Fabric, Power BI, cloud data platforms, reporting, or analytics.

Experience transitioning an organization from an MSP-supported environment toward internally managed IT. Microsoft Azure, Cisco, Security+, CISSP, ITIL, or related certifications. What Makes This Opportunity Different This is not a traditional Director position where an established IT team is already in place. It is an opportunity to build the function yourself and grow with it .

The successful candidate will have significant visibility across the organization and the ability to influence how technology is selected, implemented, secured, and scaled. As the company continues to expand, the role is expected to evolve from a highly hands-on technology leader into the leader of a broader internal IT organization.

For someone looking to take the next step into IT leadership , this position provides the opportunity to own the technology function, work directly with executive leadership, and build a department from the ground up.

What We Offer

Competitive compensation Medical, dental, and vision insurance 401(k) Paid time off Career growth and leadership opportunities Executive-level visibility and direct impact on company strategy Opportunity to build and lead an internal IT organization Opportunity to support a rapidly growing, multi-brand home-services organization About John C.

Cassidy Air Conditioning & Plumbing John C. Cassidy Air Conditioning & Plumbing has proudly served South Florida homeowners for decades. As our organization continues to grow across multiple brands and locations, we are investing in the technology, systems, and infrastructure needed to support our employees, customers, and continued expansion.

John C. Cassidy Air Conditioning & Plumbing is an Equal Opportunity Employer.