Senior Director, IT & Enterprise Applications - Remote

CentralSquare Technologies•,

3d•Remote

About The Position

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.

Requirements

AI-first transformation leadership
Oversight of all IT domains
Representation on the AI Innovation Committee
Ownership of the AI platform, playbook, and people
Ability to craft and drive vision and roadmap for AI-first internal systems
Development of progress tracking mechanisms
Coordination of cross-functional AI enablement needs
Establishment and operation of an AI-first prioritization process for IT
Ownership of the AI tool deployment playbook
Accountability for 99.9% uptime across all AI platforms
Driving a 5-domain AI org structure within IT
Partnership with CISO on data and integration governance
Championing AI adoption
Reporting IT AI metrics monthly
Ownership of IT budget allocation with an AI-first lens
Partnership with Infrastructure Team for CJIS-compliant AI governance framework
Enabling security mandates with CISO

Nice To Haves

Experience with Claude, Agentforce, Forethought, LinearB, Innovation Lab

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