Squad Leader – Health & Welfare Benefits Administration

skillventory - A Leading Talent Research Firm

full-time

Posted on: 9/25/2025

Origin: • 🇺🇸 United States

✨ AI Apply

Senior

About the role

Act as product owner and end-to-end gatekeeper of the scrum team mission, strategy, and tactical execution for Health & Welfare Benefits Administration
Partner with Fidelity leaders to influence broader strategic decisions, roadmaps and resource requirements
Set and refine squad mission and bring together chapter members to execute on specific product features
Ensure products and services are available, stable, performant, supported, and cost/maintenance managed
Maintain alignment on priorities through ongoing planning and prioritization of a product backlog
Coordinate end-to-end work across squads and enable iterative delivery, testing, experimentation and learning
Provide leadership and direction to squads focused on driving value to clients and servicing teams
Focus areas include benefits administration recordkeeping and financial accounting improvements, end-to-end capability implementation for industry trends/regulations, and participant/sponsor digital experience improvements
Define, refine, and communicate product area roadmap and acceptance criteria; measure performance against objectives and metrics
Engage with stakeholders regularly to monitor and share progress; inspect and evaluate progress and remove impediments
Collaborate with Chapter Leaders to build squad capacity, capability and enable squad member growth, development and learning
Make informed trade-off decisions balancing quality, cost, and timelines; maintain understanding of client and market needs

Bachelor’s degree required; master’s degree preferred
Scrum Product Owner Certification (CSPO) and/or Certified Employee Benefit Specialist (CEBS) or similar designations are a plus
7+ years in product management, technology and/or business
At least 7 years’ in-depth experience in the Health & Welfare outsourced administration services business, including familiarity with voice of customer and regulatory environment, preferred
Experience designing, developing and maintaining dynamic products and solutions
Hands-on agile leadership experience
Jira and Jira Align experience preferred
Data-focused approach to understanding customer needs
Ability to translate strategic objectives into action and prioritize to improve value delivered
Ability to break sophisticated product features into clear and concise stories with well-defined business value and acceptance criteria
Strong focus on execution and identifying, communicating and removing impediments
Experience driving planning, execution, and tracking progress across cross-functional teams
Ability to lead, influence, and motivate colleagues without formal authority, and build high-performing teams
Continuously improve and encourage an agile way of working; mentorship and coaching
Commitment to developing a balance of technology and non-technology skills
Note: Fidelity will not provide immigration sponsorship for this position.