[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
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