Director AI Operations

project44; Chicago (IL); On-site; USD 120,000 - 150,000; Full time

Job summary

Project 44 is seeking an experienced leader for AI Operations & Automation Delivery in Chicago, IL. This role involves owning the delivery of AI automation use cases across GIS systems and managing a diverse team of AI operations engineers and data engineers.

The ideal candidate has extensive experience in enterprise systems, strong project management skills, and the ability to drive automation initiatives using platforms like Salesforce, Snowflake, and Workato. You will collaborate with various business stakeholders to enhance system capabilities.

Qualifications

• 8+ years of experience in enterprise systems or automation engineering, at least 3 years in leadership.
• Experience operating AI or automation programs in production settings.
• Hands-on proficiency with two or more enterprise platforms.

Responsibilities

• Own end-to-end delivery of AI automation use cases across GIS systems.
• Drive automation initiatives across various platforms to increase throughput.
• Lead a team of AI operations engineers and serve as a liaison between GIS and stakeholders.

Skills

Enterprise systems experience

AI or automation program operations

Project management skills

Proficiency in Salesforce

Leadership skills

Education

8+ years in relevant field

Tools

Snowflake

NetSuite

Salesforce

Workato

Job description

At project44, we believe in better. We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world.

With our Decision Intelligence Platform, Movement, we’re redefining how global supply chains operate. By transforming fragmented logistics data into real‑time, AI‑powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next‑gen applications that keep businesses moving forward.

Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose.

AI at project44

We expect every project44 team member, regardless of role or function, to actively leverage AI in their day‑to‑day work. Whether you’re building product, serving customers, managing people, or running operations, AI is a tool you’re expected to use with intent, curiosity, and judgment. We don't expect everyone to be a data scientist. We do expect everyone to be an intelligent user of AI: able to identify where it adds value, direct it effectively, evaluate outputs critically, and govern it responsibly. We invest in our team’s AI fluency because we believe it’s a competitive advantage for every person at project44, not just our engineers.

If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high‑performance team – we should talk.

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
• 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

Diversity & Inclusion

We’re designing the future of how the world moves and is connected through trade and global supply chains. We can only deliver a truly world‑class product and experience if our teams are as diverse and unique as the communities we are building for. So it’s up to us to create a company where anyone can bring their authentic self to work every day. We’re constantly working to improve, and we accept our responsibility to elevate the voices left in the margins. It’s on every one of us.

We pride ourselves on celebrating everyone — project44 is an equal opportunity employer actively working on creating a diverse and inclusive work environment where underrepresented groups can thrive. If you share our values and our passion for helping the way the world moves, we’d love to review your application!