Senior Agile Project Manager - Medicare Technology

Required Skills & Experience

• Senior-level Program/Project Management experience with Scrum Master/Scaled Agile delivery experience in complex, cross-functional environments.
• Strong knowledge of Scrum, Kanban, and Agile methodologies.
• Familiarity with software development, DevOps, and technical delivery processes and the ability to effectively partner with technology teams.
• Strong Jira proficiency, including the ability to coach teams on consistent and effective usage.
• Demonstrated ability to work independently, prioritize effectively, make decisions, and drive execution with minimal direction.
• Strong release management experience, including risk and dependency management, readiness reporting, conflict resolution, and escalation management.
• Excellent facilitation, executive communication, and stakeholder management skills.

Job Description

Insight Global is seeking a Senior Agile Project Manager to support Technology, Business, and Operations teams to support delivery across Medicare Senior Supplemental and Ancillary products, including Medicare Supplement, Recovery Care and Home Care, Hospital Indemnity, Final Expense, Critical Illness, and Dental, Vision, and Hearing. The individual will be responsible for driving execution of complex technology initiatives across multiple teams, managing release readiness, risks, and dependencies, coaching teams on Agile practices and Jira usage, and providing targeted project/program management and financial stewardship to keep critical initiatives moving forward.

Key Responsibilities

• Program/Project Management: Lead complex, cross-functional initiatives across multiple teams and domains, driving clarity around scope, timelines, ownership, milestones, dependencies, risks, and decisions.
• Impediment Removal: Proactively identify and remove roadblocks. Escalate issues with clear options and drive mitigation through resolution.
• Stakeholder Alignment: Serve as a key liaison across Technology, Business, and Operations teams, managing expectations, resolving conflicts, and ensuring transparent communication.
• Process Improvement: Identify opportunities to strengthen Agile practices and improve delivery efficiency, quality, and effectiveness.
• Agile Coaching & Facilitation: Coach and mentor teams on Agile principles and practices while fostering a culture of accountability and continuous improvement.
• Executive Reporting: Provide clear, concise updates to senior leadership on progress, risks, dependencies, tradeoffs, and decisions needed, with an emphasis on early visibility and proactive issue management.