project44

Director AI Operations

project44 • $130K — $180K *
Chicago, IL 60629In-Person
Information Technology
8 - 10 years of experience
Today
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Job Overview by Ladders

Qualifications

  • 8+ years in enterprise systems or IT operations, with 3+ years in leadership
  • Proven experience operationalizing AI or automation programs
  • Hands-on proficiency with Salesforce, NetSuite, Snowflake, or similar platforms
  • Experience managing integration architecture across SaaS systems
  • Strong project management skills with multiple concurrent initiatives

Responsibilities

  • Own AI automation delivery across GIS systems from scoping to operations
  • Manage GIS AI project portfolio on the Jira board
  • Drive automation initiatives across various enterprise systems
  • Administer GIS Project Intake and Business Requirements
  • Oversee GIS data integration architecture through Snowflake as a truth source
  • Lead a team of AI engineers and technical program managers
  • Serve as liaison between GIS and business stakeholders

Benefits

  • In-office commitment of four days a week to foster collaboration
  • Opportunities for team development and skill growth
  • Engagement with executive leadership for program insights
  • Access to a diverse range of enterprise platforms and technologies
Full Job Description
About the Role

AI Operations & Automation Delivery
  • 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

AI Builder Governance & Citizen Developer Program
  • 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

Systems & Data Integration
  • 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

Team & Stakeholder Leadership
  • 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

Key Responsibilities

Required
  • 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

Preferred
  • 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


How Success Is Measured

In the first 12 months, this leader will be evaluated on:
  • AI project portfolio delivery rate % of committed AI Operations initiatives shipped on time and within scope
  • Automation ROI - documented hours of manual effort eliminated per quarter across GIS functions
  • System reliability - uptime and SLA adherence for Workato recipes, Snowflake views, and Lovable-based tools
  • Stakeholder satisfaction - quarterly feedback scores from GIS business partners (Finance, Sales Ops, Legal, HR)
  • Team development - evidence of skill growth, retention, and hiring progress within the GIS AI team
  • In-office Commitment: Employees are expected to contribute to our collaborative culture by working in the office Four days weekly

About project44

project44 is a logistics technology company that provides cloud-based transportation management solutions. The company's platform provides real-time visibility into the transportation supply chain, enabling shippers, carriers, and logistics service providers to improve operational efficiency, reduce costs, and enhance customer satisfaction. project44's solutions include carrier onboarding, real-time tracking, predictive analytics, and automated freight invoice auditing. The company serves customers in various industries, including retail, manufacturing, and healthcare.
Learn more about project44
Size
500 employees
Industry
Information Technology
Founded
2014
* Ladders Estimates

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