Senior Director, IT & Enterprise Applications - Remote

What We’re About

At CentralSquare, we don’t just build software - we power public servants and uplift communities with Hero-Grade Technology. Every line of code, every feature we deliver helps heroes across North America protect, serve, and save lives. When you join us, you become part of a mission-driven team creating technology that makes communities safer and stronger.

Your Growth Matters. We believe heroes deserve opportunities to rise. That’s why we invest in your career with mentorship, learning programs, and clear paths for advancement. If you’re motivated, there’s no limit to how far you can go.

Your Commitment Deserves Reward. We offer competitive compensation and a benefits package designed to support your life inside and outside of work—tuition reimbursement, parental leave, paid volunteer hours, and unlimited PTO. Plus, our flexible work environment gives you the freedom to balance your heroic work with personal well-being, whether you’re in the office or remote.

Join us and help build the tools that power real-life heroes. Together, we make a difference.

The Role

This role will lead CentralSquare's internal IT organization through its AI-first transformation. In addition to overseeing all IT domains, this role represents IT on the AI Innovation Committee, the cross-functional group where every function sends a representative to coordinate AI adoption company-wide. Internal IT is the enablement backbone that makes AI possible for every other function: this role owns the platform, playbook, and people that make that true.

Key Responsibilities:

• Craft and drive the vision and roadmap for internal systems that is AI-first, and communicate it across the IT organization and to key stakeholders
• Develop mechanisms to track progress against that roadmap
• Represent IT on the AI Innovation Committee; coordinate cross-functional AI enablement needs alongside representatives from every other function
• Establish and run an AI-first prioritization process for IT: define an intake process for IT projects, run a regular cadence to prioritize and commit to system changes, and report out on progress
• Own the AI tool deployment playbook: meet roadmap timeline goals from approval to live for any new AI tool
• Hold accountability for 99.9% uptime across all AI platforms (Claude, Agentforce, Forethought, LinearB, Innovation Lab, future tools)
• Drive the 5-domain AI org structure within IT: AI Platform & Security, AI Data & Integrations, AI-Powered Applications, AI-First IT Support, AI Ops
• Partner with the CISO on governance around data and integration use, including MCP governance
• Champion Claude adoption across the company, from 144 users to org-wide saturation, as part of IT's role as the AI enablement backbone
• Report IT AI metrics monthly: platform uptime, helpdesk deflection rate, AI tool deployment velocity
• Own IT budget allocation and accountability to expense goals with an AI-first lens; prioritize Accelerator and Enabler tier initiatives
• Partner with Infrastructure Team to build and maintain a CJIS-compliant AI governance framework
• Partner with the CISO to enable security mandates across Platform & MCP/Integrations within established timelines

AI Success Metrics:

• 99.9% AI platform uptime (Claude, Agentforce, Forethought, etc.)
• New AI tool deployment SLA: meet roadmap timeline goals from approval to live
• 40% IT helpdesk tier-1 deflection via AI by end of 2026
• 100% of AI Accelerator tasks in active progress by Q2 2026