[Remote] Technical Program Manager

Note: The job is a remote job and is open to candidates in USA. Grey Parrot Systems is a women-owned, BEP-certified IT services firm headquartered in Naperville, Illinois, delivering AI-first, governance-driven digital transformation for mid-market enterprises. The Technical Program Manager will manage multiple concurrent technical programs, proactively resolve risks and blockers, communicate with C-suite executives, and use AI-assisted tools to accelerate reporting, planning, and delivery.

Responsibilities

• Own delivery across multiple concurrent programs — scope, schedule, risks, dependencies, and stakeholder management simultaneously
• Identify and resolve risks and blockers before they surface as problems — proactively, without being asked
• Communicate program status, risks, and decisions to C-suite executives with clarity, confidence, and composure
• Use Claude daily to accelerate program reporting, risk analysis, and stakeholder communications
• Lead steering committee meetings and executive program reviews — driving decisions, not just presenting updates
• Apply AI-DLC delivery practices across all managed programs — MCP workflows, AI-assisted sprint planning, and intelligent delivery tooling

Skills

• 8–12 years of technical program management experience — multiple concurrent programs across engineering, data, cloud, and enterprise platform workstreams
• Exceptional C-suite communication — translating technical delivery realities into executive language that drives decisions
• AI-DLC delivery experience — managing programs built on Claude Code, Cursor, GitHub Copilot, and AI-assisted engineering workflows
• Hands-on Claude experience — generating status reports, risk summaries, stakeholder briefings, and program plans at speed
• Expert-level Jira — advanced configuration, JQL, dashboards, and cross-program reporting
• Proven proactive delivery mindset — track record of on-time delivery across complex multi-program portfolios
• Strong Agile / hybrid delivery experience — Scrum, Kanban, and waterfall workstreams simultaneously
• Location: Naperville / Chicago, IL — Remote
• Experience: 8–12 years

Benefits

• Remote work arrangement

Company Overview

Enterprise AI. From Strategy to Scale. Most organizations can launch AI pilots. It was founded in 2023, and is headquartered in Naperville, Illinois, USA, with a workforce of 51-200 employees. Its website is https://gparrot.io.

Company H1B Sponsorship

Grey Parrot Systems LLC has a track record of offering H1B sponsorships, with 4 in 2026, 4 in 2025, 7 in 2024. Please note that this does not guarantee sponsorship for this specific role.