Senior Director, Information Technology

Key Responsibilities 

• Lead IT strategy and roadmap planning: Own and drive a multi-year IT roadmap that supports Whistle’s growth, operating model, and business priorities across Operations, Finance, HR, Real Estate, M&A, and other functions. 

• Build strong technology governance: Establish practical IT policies, standards, and controls for cloud and on-premise environments, including Microsoft 365, data privacy, endpoint security, DLP, and identity management. 

• Oversee user access and compliance: Lead role-based access design, access reviews, deactivation controls, and compliance processes to support audit readiness and protect company data. 

• Improve systems and processes: Identify opportunities to modernize platforms, improve integrations, automate manual work, and simplify how teams use technology across the business. 

• Lead change management and stakeholder communication: Serve as a clear, credible communicator for technology initiatives, helping leaders and teams understand what is changing, why it matters, and how it supports the business. 

• Manage network and help desk performance: Provide oversight for network infrastructure, help desk support, escalation paths, and service levels in partnership with the ISP, MSP, and internal stakeholders. 

• Champion security awareness: Partner with the MSP to configure, launch, and monitor security training campaigns that build awareness and reduce risk across the organization. 

• Serve as a business partner: Work closely with leaders across the company to understand needs, prioritize initiatives, and ensure technology solutions are practical, scalable, and adopted by the field and support teams. 

• Own the IT budget: Manage the annual IT budget, including applications, hardware, SaaS tools, MSP services, software licensing, and technology-related capital investments. 

• Manage vendor relationships: Lead IT vendor selection, contract negotiations, SLA governance, and ongoing performance management to ensure strong service, cost discipline, and business alignment. 

Qualifications 

• Bachelor’s degree in Information Systems, Information Technology, Computer Science, or a related field required; relevant certifications in IT governance, infrastructure, security, or cloud platforms preferred. 

• 12+ years of progressive IT experience, including at least 3 years in a senior leadership role. 

• Strong hands-on experience with network architecture, security, Microsoft 365, Azure or other cloud platforms, systems integration, and enterprise application support. 

• Experience supporting a multi-site, high-growth retail, service, or field operations environment preferred. 

• Ability to translate technical concepts into clear business recommendations for executive and non-technical audiences. 

• Proven ability to lead enterprise-scale IT programs from strategy through execution, delivering on time and within budget. 

• Strong judgment, calm leadership, and the ability to operate effectively in a fast-paced, changing environment.