Director / Senior Director, AI Operations

project44•Chicago, IL

3d•Hybrid

About The Position

This role is responsible for the end-to-end delivery of AI automation use cases across GIS systems, from scoping and build through deployment and ongoing operations. The position involves managing the GIS AI project portfolio, driving automation initiatives across various systems to reduce manual intervention and increase throughput, and participating in the creation of server infrastructure that connects LLMs to enterprise systems. Additionally, the role includes administering and enforcing AI Builder governance, maintaining a project registry, and serving as the approval authority for new AI tool deployments within the GIS domain. The position also oversees the GIS data integration architecture, collaborates with peer leaders on cross-functional automation, and leads a team of AI operations engineers, data engineers, and technical program managers. The Director/Senior Director will serve as the primary liaison between GIS and business stakeholders for AI-driven system enhancements and partner with leadership on OKR planning, capacity management, and AI investment prioritization, presenting program status, risks, and outcomes to executive sponsors.

Requirements

8+ years of experience in enterprise systems, IT operations, or data/automation engineering, with at least 3 years in a leadership role
Demonstrated experience operating AI or automation programs in production — not just piloting or evaluating
Hands-on proficiency with at least two of: Salesforce, NetSuite, Snowflake, UKG, Workato, or similar enterprise platforms
Experience managing integration architecture across multiple SaaS systems, including data pipelines and API-driven workflows
Strong project management skills; experience owning a portfolio of concurrent technical initiatives
Comfortable presenting technical concepts and program status to executive audiences

Nice To Haves

Experience with Snowflake
Familiarity with MCP (Model Context Protocol) server patterns and LLM API integration
Experience with Supabase, Lovable, or modern React-based no-code / vibe-coding platforms
Working knowledge of Azure AD / Entra ID, OIDC/SAML, PKCE flows, and RBAC design
Knowledge of GitHub Actions, automated security scanning, or DevSecOps practices

Responsibilities

Own end-to-end delivery of AI automation use cases across GIS systems — from scoping and build through deployment and ongoing operations
Manage the GIS AI project portfolio on the Jira AI Operations board, maintaining accurate status, priority, and resource alignment
Drive automation initiatives across Workato, Snowflake, Salesforce, NetSuite, Ironclad, and other systems — reducing manual intervention and increasing throughput across GIS functions
Participate in the MCP (Model Context Protocol) server infrastructure creations that connect Claude and other LLMs to enterprise systems via governed API patterns
Administer and enforce the GIS Project Intake and Business Requirements — including role-based access tiers, controls, and project submission workflow
Maintain the Project Registry, ensuring all Lovable/vibe-coded and AI-assisted apps are catalogued, BRD-linked, and security-reviewed
Serve as the approval authority for new AI tool deployments within the GIS domain, coordinating with InfoSec, Legal, and IT Operations
Oversee the GIS data integration architecture — Salesforce, NetSuite, UKG, Zendesk, Clari, Ironclad, and others through Snowflake as the single source of truth
Collaborate with peer leaders within GIS on cross-functional automation and AI-assisted workflows
Lead and develop a team of AI operations engineers, data engineers, and technical program managers within GIS
Serve as the primary liaison between GIS and business stakeholders (Finance, Sales Ops, Legal, HR) for AI-driven system enhancements
Partner with the VP of GIS and CFO organization on quarterly OKR planning, capacity management, and AI investment prioritization
Present program status, risks, and outcomes to GIS leadership and executive sponsors on a regular cadence