Senior Product Manager - Agentic AI Chicago, IL

At Four Kites we have the opportunity to tackle complex challenges with real-world impacts. Whether it’s medical supplies from Cardinal Health or groceries for Walmart, the Four Kites platform helps customers operate global supply chains that are efficient, agile and sustainable.

Join a team of curious problem solvers that celebrates differences, leads with empathy and values inclusivity.

Four Kites has evolved from multimodal freight visibility into a comprehensive platform spanning yard management, appointment scheduling, order visibility, inventory insights, and purchase order tracking. With AI transformation accelerating, we're creating a new category of data‑led product SKUs that unlock cross-functional value by connecting our rich dataset across hundreds of shippers and thousands of carriers.

Senior Product Manager, Agentic AI

The Opportunity

We're seeking an innovative Agentic AI Product Manager to drive the next generation of our AI‑powered Digital Workers. You'll develop autonomous AI agents that transform supply chain operations - digital workers that can learn, collaborate, and automate complex workflows. This role requires both strategic product thinking AND hands‑on technical capability.

Location:

Chicago preferred. Open to remote with monthly travel to Chicago

What You’ll Do

• Define and execute the product roadmap for agentic AI solutions within Four Kites’ Intelligent Control Tower

• Own product P&L, adoption metrics, and customer outcomes

• Drive go‑to‑market strategy with sales and customer success teams

• Develop business cases for new digital workers that can automate routine supply chain tasks

• Shape the long‑term vision aligned with our shift from 'software‑as‑a‑service' to 'service‑as‑software'

Technical Product Development (40%)

• Lead end‑to‑end product lifecycle for autonomous AI agents from concept to launch

• Build proof‑of‑concepts and prototypes using AI tools (Cursor.ai or equivalent) to demonstrate value

• Mine and analyze data using SQL/Python to gain usage insights and validate hypotheses

• Define agent capabilities, learning mechanisms, and collaboration frameworks between multiple AI workers

• Create detailed requirements for reasoning capabilities, decision trees, and action frameworks

• Run A/B tests and establish metrics for agent performance

• Engage directly with enterprise customers to identify high‑value use cases and pain points

• Translate complex supply chain workflows into autonomous agent behaviors

• Present product vision and roadmap to customers at events like Four Kites Summit

• Collaborate with data science teams to leverage Four Kites’ 3.2M daily supply chain events for agent training

Success Metrics (Year
1)

• Achieve 90% customer retention for AI agent products

• Achieve 80%+ adoption on new features released

• Demonstrate measurable automation rates and ROI for enterprise customers

• Launch 2‑3 new digital workers with proven business impact

Required Qualifications

Experience

• 5+ years of product management experience in fast‑growing SaaS companies

• At least 2 years focused on AI/ML products with proven track record in enterprise B2B

• Experience with autonomous systems, conversational AI, or intelligent automation

• Supply chain domain expertise:
Deep understanding of operational challenges (shipper pain points, yard management, multimodal logistics)

Technical Skills

• Hands‑on ability with Cursor.ai or equivalent tools to quickly build prototypes

• Proficiency in SQL and Python to independently explore data and insights

• Strong understanding of LLMs, reinforcement learning, and multi‑agent systems

• Experience with API design and system architecture

Soft Skills

• Self‑starter mindset:
Thrives in ambiguity, identifies opportunities without waiting for detailed briefs

• Excellent communication skills for presenting to customers, executives, and technical teams

• Proactive problem‑solving with hunger to learn and collaborate

• Data‑driven decision making with strong analytical capabilities

Education

• Bachelor’s degree in Computer Science, Engineering, or quantitative discipline

• MBA or advanced degree in AI/ML is a plus

What Makes You Stand Out

• Experience building products…