Senior Technical Project Manager (Generative AI & Agentic Initiatives)

Instant Alliance, LLC; Chicago (IL); Hybrid; USD 140,000 - 180,000; Full time

Job summary

Instant Alliance, LLC seeks a Senior Technical Project Manager to lead cross-functional delivery for Generative AI and agentic workflows, bridging Python-based AI engineering and executive stakeholders from concept to production.

The role supports hybrid or onsite work in Chicago, IL, with a preference for candidates familiar with enterprise compliance environments. Strong PM experience and stakeholder management are essential.

Qualifications

• 5+ years of technical project/program management experience delivering complex software, data, or AI/ML initiatives in Agile environments.
• Demonstrated experience managing technical engineering teams building production-grade software or AI applications.
• Familiarity with modern AI concepts, LLM lifecycles, and technical terminology to effectively partner with engineering leads.

Responsibilities

• Own the end-to-end roadmap, sprint planning, backlog grooming, and delivery milestones for complex GenAI and multi-agent software projects.
• Act as the bridge between AI engineers and executive stakeholders, translating technical complexity into clear business value.
• Coordinate across cross-functional teams (Engineering, Data Science, Security, Legal, and Product) to align dependencies, manage scope, and mitigate risks.
• Establish agile cadences, tracking metrics, and accountability frameworks tailored for rapid AI product development cycles.
• Ensure solutions meet enterprise compliance, security, and change management standards.

Skills

Project management

Technical leadership

Agile methodologies

Stakeholder management

Cross-functional coordination

Communication

Tools

Python

LangGraph

APIs

RAG architectures

Job description

Position Overview

We are looking for an experienced Senior Technical Project Manager to lead cross-functional delivery for high-impact Generative AI and agentic workflow initiatives. In this role, you will bridge technical engineering teams (working with LangGraph, MCP, and custom LLM applications) and business stakeholders, driving execution from proof-of-concept through production rollout.

While the ideal candidate is based in Chicago, IL, exceptional candidates with strong remote track records will be considered. A strong preference will be given to candidates with prior project management experience within the aviation, travel, or airline industry (specifically United Airlines), enabling them to navigate complex enterprise environments, legacy systems, and compliance frameworks from day one.

Key Responsibilities

• Program & Project Delivery: Own the end-to-end roadmap, sprint planning, backlog grooming, and delivery milestones for complex GenAI and multi-agent software projects.

• Technical Translation: Act as the vital bridge between deep technical AI engineers (Python, LangGraph, RAG architectures) and executive/business stakeholders, translating technical complexity into clear business value.

• Stakeholder & Vendor Management: Coordinate across cross-functional teams (Engineering, Data Science, Security, Legal, and Product) to align dependencies, manage scope, and mitigate risks.

• Process & Governance: Establish agile cadences, tracking metrics, and accountability frameworks tailored for rapid, iterative AI product development cycles.

• Operational Readiness: Ensure solutions meet enterprise compliance, security, and change management standards, particularly within airline or large-scale enterprise ecosystems.

Qualifications & Requirements

• Location: Preference for Chicago, IL (hybrid/onsite flexibility), open to exceptional remote candidates for the right fit.

• Project Management Expertise:

  • 5+ years of technical project/program management experience delivering complex software, data, or AI/ML initiatives in Agile environments.

  • Demonstrated experience managing technical engineering teams building production-grade software or AI applications.

  • Familiarity with modern AI concepts, LLM lifecycles, and technical terminology (RAG, agentic workflows, APIs) to effectively partner with engineering leads.

• Industry Experience:

  • Strong preference for previous project management experience at United Airlines or major airline/aviation organizations, with a solid understanding of airline operational tech or enterprise workflows.

• Core Competencies:

  • Exceptional communication, executive presence, and stakeholder management skills.

  • Proven ability to unblock engineering teams, anticipate risks, and drive projects to timely completion under tight deadlines.