Program Manager & AI Automation Lead
Summary
A 10-month, project-based W2 contract in San Diego blending technical program management (leading execution across 55+ production services, incident/RCA tracking, executive reviews) with hands-on building of AI-agent-driven automation for ticketing, reconciliation, and reporting using tools like Jira, Smartsheet, and Claude. Pays $80–100/hour.
We're seeking a Program Manager & AI Automation Lead to lead a high-impact technical initiative focused on strengthening operational excellence while automating the manual processes that support it. You’ll combine hands-on technical program management with the design, build, and delivery of AI-agent-driven automation, with working solutions as a core project deliverable.
The role brings together two key capabilities: technical program management and agentic automation delivery, requiring someone who can drive complex cross-functional work while personally building automation that improves how programs operate.
Key Responsibilities
Lead program execution across a portfolio of 55+ production services, including executive operating reviews, incident and RCA tracking, readiness activities, and cross-functional initiatives.
Establish program scope, priorities, milestones, dependencies, deliverables, and success measures while coordinating execution across multiple teams.
Identify and prioritize opportunities to streamline or replace manual program processes through automation.
Design, build, and productionize AI-agent automation, including ticketing and routing, cross-platform reconciliation, program telemetry, executive reporting, and automated follow-up workflows.
Direct multiple AI agents toward defined outcomes, establishing appropriate context, acceptance criteria, validation controls, and human-in-the-loop processes.
Ensure automation is reliable, auditable, and maintainable, with appropriate documentation and runbooks.
Communicate program progress, risks, decisions, and outcomes clearly and concisely to senior technology leadership.
Build strong cross-functional relationships and drive commitments through influence, proactive communication, and consistent follow-through.
Qualifications
7+ years of technical program management experience in platform, infrastructure, or high-scale technology environments, with a proven track record leading complex technology initiatives from planning through implementation and transition.
Hands-on experience designing and delivering AI-agent-driven automation connected to live data and workflows.
A track record of personally building automation and workflows yourself, including API integrations to tools like Jira and Smartsheet, building dashboards and tracking systems, and hands-on experience with AI/agent tools (like Claude, agent frameworks, or similar integration methods).
Ability to provide examples of automation you've built and shipped, and can clearly explain your individual contribution, how you designed the solution, and the outcomes it produced.
Experience with AI governance, including validation controls, auditability, and human-in-the-loop processes.
Strong operational knowledge of incident management, SDLC, and distributed systems; identity, security, or authorization experience is a plus.
Excellent executive communication and the ability to drive cross-functional delivery through influence.
Highly proactive and comfortable operating in fast-moving, complex technology environments.
Duration: 40 hours a week, 10 months
Type: Project-Based Hourly W2, Benefits Eligible
Rate: $80-100/hour
Skills
As published by ashby · 11 questions · 1 written answer
Basics
Name, Email, Resume
Short answers (3)
- Phone Number
- Location
- LinkedIn Profile
Pick from a list (6)
- Are you legally authorized to work in the United States?
- Will you now, or in the future, require sponsorship for employment visa status (e.g. H-1B visa status)?
- How many years of technical program management experience do you have specifically within platform, infrastructure, or high-scale technology environments (e.g., managing a portfolio of 50+ production services)?
- Have you personally designed, built, and deployed (to production) an AI-agent-driven or workflow automation tool yourself?
- Which of the following have you personally used to build automation or integrations? (Select all that apply)
- Have you implemented validation controls, auditability, or human-in-the-loop checkpoints for an AI agent or automated workflow operating with minimal supervision?
Written answers (1)
- Please provide a written summary of at least one automation project you personally built and shipped, including your specific role, the tools/platforms used, and the measurable outcome.
Attachments (1)
- Optional Cover Letter optional
