Senior Director, Information Technology

Whistle is seeking a strategic, hands-on Senior Director of Information Technology to lead our technology strategy, governance, infrastructure, and support model across a fast-growing, multi-site organization. This role partners closely with executive leadership, business teams, vendors, and our Managed Service Provider to ensure our systems are secure, scalable, reliable, and aligned to the needs of the business. The Senior Director will lead IT roadmap planning, Microsoft 365 and cloud governance, network and help desk operations, data and access controls, vendor management, and technology lifecycle planning across 450+ company locations., * 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.

• 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.