The ProblemFlock's workforce is expanding across distributed hubs, remote teams, and specialized field services. Supporting this team requires a self-insured benefits strategy that pairs high-quality employee care with disciplined financial stewardship and active plan management. You will take full ownership of our health plans, vendor migrations, and leave administration, turning a complex multi-plan setup into a reliable, easy-to-navigate experience for every employee.
What You'll Own- Lead end-to-end plan administration and critical carrier transitions, including broker alignment, health plan migrations, and 401(k) recordkeeper updates.
- Manage day-to-day relationships and service accountability across our core and specialty benefits partners, including Maven, Caraloop, and Allied.
- Run leave administration across FMLA, parental leave, short-term disability, and state-specific leave requirements, serving as the dedicated point of contact for employees and managers.
- Partner with Payroll and Finance to audit enrollment files, reconcile payroll deductions for HSA, FSA, and 401(k) contributions, and monitor self-insured claims data.
- Deliver clear, accessible benefits communications and open enrollment education tailored to corporate employees, remote workers, and hourly field service teams.
What This Role is Not- This isn't a hands-off strategy role, you will dig directly into claims data, resolve employee coverage escalations, and manage enrollment files alongside long-term planning.
- You will not manage direct reports in year one, this is an individual contributor role focused on direct execution, though there is room to expand the scope over time.
- This isn't an isolated benefits island, you will collaborate daily with People Operations, HRBPs, and Finance to ensure benefits operations align cleanly with payroll and company policies.
What You Bring- Hands-on experience administering self-insured and fully insured employee health and welfare plans across multiple coverage tiers.
- Demonstrated track record managing vendor or carrier implementations, broker transitions, or retirement plan cutovers.
- Practical knowledge running leave of absence workflows across FMLA, short-term disability, and multi-state leave regulations.
- Experience supporting diverse employee populations, particularly a mix of remote staff, corporate employees, and distributed field service teams.
- Background supporting European or international employee benefits is a plus.
CompensationIn this role, you'll receive a starting salary between $120,000 and $150,000 as well as Flock Stock Options. Base salary is determined by job-related experience, education/training, as well as market indicators. Your recruiter will discuss this in depth with you during our first chat.
