Senior Agile Leader - Health Insurance Technology

Job Description Insight Global is seeking a Senior Agile Leader to support a large health insurance client of ours. This role sits within an enterprise PMO team and partners closely with a technology team to deliver Medicare Senior Supplemental and Ancillary products. You'll lead Agile delivery with high independence and strong judgment to drive outcomes—facilitating PI-level and cross-team execution, managing release readiness and risks, coaching teams on Agile practices and Jira usage, and taking on targeted project/program management and financial stewardship responsibilities to keep critical work moving. What You'll Do

•  Serve as the day-to-day Senior Scrum Master for 2-3 small Scrum teams, ensuring strong execution across ceremonies, flow, commitments, and delivery outcomes
•  Be prepared to program manage complex, cross-functional projects across multiple teams and domains as needed, driving clarity on scope, owners, milestones, dependencies, and decisions
•  Assume some parts of an RTE role- examples: Lead Scrum of Scrums and other cross-team forums; actively manage and drive closure on risks, dependencies, and cross-team blockers
•  Own risk management end-to-end: identify, escalate with options, and drive mitigation through to resolution
•  Remove impediments by coaching teams and partners, negotiating tradeoffs, and unblocking decision paths—not just "tracking issues"
•  Own release management activities, including GitHub helper reporting (release sign-off critical path) and release night escalation support
•  Facilitate PI retrospectives and continuous improvement (including Agile coffee chat format)
•  Champion Jira and Agile tooling (including migration "Day 2" coordination and Jira-integration-friendly PI planning)
•  Maintain Medicare delivery/reporting hygiene (e.g., Medicare Reporting database entries based on release notes)
•  Produce executive-level status reporting: clear, concise updates for senior leaders on progress, risks, decisions needed, and tradeoffs, with a bias toward early visibility
•  Handle defined PM/ops ownership where needed (e.g., ITPR management, timesheet audit/backup approval coverage, SSI Space Owner stewardship)
•  Reinforce team culture through simple, consistent morale practices We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day.

We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.

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https://insightglobal.com/workforce-privacy-policy/. Skills and Requirements

•  Senior-level Scrum Master / Scaled Agile delivery experience in complex, cross-team environments
•  Strong Jira fluency and the ability to coach others in consistent, decision-supporting usage
•  Financial literacy: experience with Clarity tool - tracking spend, managing allocations, forecasting run-the-business vs. project work, and balancing delivery tradeoffs within budget constraints
•  Proven ability to work independently: prioritize, decide, and drive execution with minimal direction
•  Release management experience (risk/dependency management, readiness reporting, escalation handling)
•  Strong facilitation and stakeholder communication skills