Senior Director, IT & Enterprise Applications

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.

This role will lead CentralSquare's Internal IT organization through its AI-first transformation. In addition to overseeing all IT domains, role will hold the IT seat on the AI Innovation Board and is personally accountable for IT's role as the AI Enablement backbone for the entire company. Every function's AI goals have an IT dependency — this role owns the platform, playbook, and people that make those goals possible.

•       Craft and drive vision and roadmap of our internal systems that is AI-first and communicate it with executive leadership across CST

•       Develop mechanisms by which to track progress against the above vision.

•       Serve as IT's representative on the AI Innovation Board; coordinate cross-functional AI enablement needs

•       Establish and run an AI-first prioritization process for IT – clearly define intake process for IT projects with regular cadence to prioritize and commit to system modifications and changes. Report out on progress in meeting commitments.

•       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: AI Platform & Security, AI Data & Integrations, AI-Powered Applications, AI-First IT Support, AI Ops

•       Establish governance around data and integration use – partnering with CISO on MCP governance.

•       Champion Claude adoption across the company — from 144 users to org-wide saturation

•       Report IT AI metrics monthly: platform uptime, helpdesk deflection rate, AI tool deployment velocity

•       Own IT budget allocation and accountability to expense goals with AI-first lens — prioritize Accelerator and Enabler tier initiatives

•       Build and maintain CJIS-compliant AI governance framework with Greg Cook

•       Partner with CISO to enable security mandates across Platform & MCP/Integrations within established timelines

•       99.9% AI platform uptime (Claude, Agentforce, Forethought, LinearB)

•       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

•       5+ years IT leadership with strong enterprise applications background

•       Demonstrated AI adoption — already using Claude and AI tools in daily workflow

•       Cross-functional communicator — comfortable with PE board-level reporting

•       CJIS compliance awareness; public sector IT governance experience a plus

•       Strong project portfolio management across multiple concurrent workstreams