Benefit Services Senior Leader - Group Fulfillment
Senior people leader managing 3-5 managers and ~40 specialists in Group Fulfillment operations. Sets operational strategy, drives AI automation, coaches leaders, and ensures accurate on-time benefits delivery for small business customers.
Responsibilities
- Lead 3-5 managers and ~40 specialists, running structured cadences including weekly 1:1s, team forums, and monthly business reviews
- Coach leaders to operate as drivers, owning change rationale, marketing it to teams, and holding performance standards
- Develop leaders through structured calibration, performance reviews, and clear evidence-based expectations
- Set and own operational objectives, policies, and work plans for Group Fulfillment with accountability for headcount and capacity planning
- Deliver against timeliness, accuracy, and completeness standards for benefits fulfillment
- Manage cross-functional dependencies with Onboarding, Licensed Benefits Advisors, Member Fulfillment, BizOps, and carrier partners
- Set the AI vision and own the automation roadmap for Group Fulfillment
- Coach AI fluency through leaders via office hours, working sessions, and partnerships with Data, Engineering, and Product
- Own change rationale with a clear playbook: what's changing, why, impact, resources, and ownership
- Make decisions within authority quickly, communicate clearly, and maintain decisions through friction
- Run calibrated, evidence-based performance cycles holding high standards with AI fluency as non-negotiable
- Develop high-potential ICs and managers through stretch work, cohort programs, and sponsorship; address underperformance early
Requirements
- 5+ years of leadership experience, including 2 years leading other leaders (preferred)
- Demonstrated track record of setting operational strategy, owning a budget, and accountability for business-segment impact
- Experience driving meaningful org change (restructures, role evolution, process redesign, scaling) and bringing teams through it
- Driver mindset: own change rationale, make decisive decisions, communicate once, bring data-backed proposals
- Comfortable reading dashboards, interrogating data, and identifying gaps proactively
- Track record operating against time-sensitive SLAs in benefits, healthcare, payroll, banking, insurance, or comparable regulated operations
- Manage costs and capacity as a leader
- Actively use AI to redesign leadership workflows; personally redesigned/automated workflows, built agents, or prototyped tools that changed team operations
- Coach AI fluency in others, evaluate tools with judgment, teach teams to use AI differently, hold accountability for adoption
- Develop leaders through structured coaching; hold performance bar with care through early hard conversations
Nice-to-Haves
- Experience in benefits operations, health insurance brokerage, employee benefits administration, or payroll
- Experience with carrier portals, Salesforce, and high-volume operational tooling
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