Technical Program Manager

Grey Parrot Systems (GPARROT) is hiring a Technical Program Manager who is proactive, exceptionally communicative, and gets programs delivered on time — every time.About Grey Parrot SystemsGrey Parrot Systems is a women-owned, BEP-certified IT services firm headquartered in Naperville, IL. We deliver AI-first, governance-driven digital transformation for mid-market enterprises — and we're growing.About the RoleYou manage multiple concurrent technical programs without dropping a thread. You see risks before they become problems. You walk out of C-suite meetings having driven a decision — not just presented an update. You use Claude to generate a board-ready status brief in 20 minutes — and it is good. If this sounds like you — read on.Must-Have Skills8–12 years of technical program management experience — multiple concurrent programs across engineering, data, cloud, and enterprise platform workstreamsExceptional C-suite communication — translating technical delivery realities into executive language that drives decisionsAI-DLC delivery experience — managing programs built on Claude Code, Cursor, GitHub Copilot, and AI-assisted engineering workflowsHands-on Claude experience — generating status reports, risk summaries, stakeholder briefings, and program plans at speedExpert-level Jira — advanced configuration, JQL, dashboards, and cross-program reportingProven proactive delivery mindset — track record of on-time delivery across complex multi-program portfoliosStrong Agile / hybrid delivery experience — Scrum, Kanban, and waterfall workstreams simultaneouslyWhat You'll DoOwn delivery across multiple concurrent programs — scope, schedule, risks, dependencies, and stakeholder management simultaneouslyIdentify and resolve risks and blockers before they surface as problems — proactively, without being askedCommunicate program status, risks, and decisions to C-suite executives with clarity, confidence, and composureUse Claude daily to accelerate program reporting, risk analysis, and stakeholder communicationsLead steering committee meetings and executive program reviews — driving decisions, not just presenting updatesApply AI-DLC delivery practices across all managed programs — MCP workflows, AI-assisted sprint planning, and intelligent delivery toolingToolsClaude · Jira · Confluence · Azure DevOps · Smartsheet · Claude Code · Cursor · GitHub Copilot · MCP · Microsoft 365 · Power BIThe Right CandidateSends the status report before anyone asksCalls out Friday's crisis in Monday's standupManages five programs and makes each team feel like the only oneDetailsLocation: Naperville / Chicago, IL — RemoteExperience: 8–12 yearsType: Full-TimeStart: ImmediateGrey Parrot Systems is an Equal Opportunity Employer. As a women-owned, BEP and WBENC-certified firm, diversity and inclusion are core to who we are. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, marital status, or any other legally protected characteristic. Reasonable accommodations are available upon request.Stay Connected👉 https://www.linkedin.com/company/gparrot/