Senior Director, IT & Enterprise Applications - Remote

CentralSquare Technologies is Hero-Grade. As the trusted provider of public sector software in North America, more than 8,000 agencies rely on our comprehensive, cloud-based platform to manage critical operations - from dispatch to records, permitting to payroll. We serve with purpose and stand together with our heroes, committed to supporting the public sector with software built for impact.
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
Requirements
5+ years IT leadership experience, including demonstrated experience owning and transforming an IT team
Demonstrated AI adoption: already using Claude and AI tools in daily workflow
Strong cross-functional communicator, comfortable partnering with security, legal, and other internal stakeholders
CJIS compliance awareness; public sector IT governance experience a plus
Strong project portfolio management across multiple concurrent workstreams
Additional Considerations
Bachelors Degree in Information Technology (or similar), or equivalent experience
Experience leading both direct and indirect teams of up to 30+ individual contributors

Work arrangement
Yes