Own benefits strategy and day-to-day operations for a growing, multi-state company where employee experience and compliance have to stay airtight. If you’ve managed self-funded health plans, live in Workday, and can translate complex benefits into clear employee guidance, this role puts you at the center of Total Rewards impact.
About Kin Insurance
Kin is a direct-to-consumer digital insurer modernizing home insurance with smarter pricing, seamless bundling, and a simpler customer experience. As Kin grows, they’re investing in strong People Operations and Total Rewards to support employees across a distributed workforce.
Schedule
- Full-time, remote
- Department: People
- Deadline to apply: January 29, 2026 at 11:00 PM CST
- Compensation range: $120,000–$135,000 (plus equity/RSUs)
- Reporting to: VP, Total Rewards & People Operations
What You’ll Do
- Serve as the go-to expert on Kin’s benefit programs, employee resources, and vendor support
- Stay current on benefits trends, compliance changes, and market best practices
- Manage operations and administration of self-insured health plans and programs, including:
- Medical, dental, vision
- Ancillary coverages
- FSA, HSA
- COBRA
- Manage 401(k) operations and administration, including:
- Accurate enrollments and deferral rates
- Payroll contribution accuracy
- Compliance tasks and audits
- Employee issue resolution
- Lead annual open enrollment by partnering with carriers, supporting employee questions, and creating communications
- Partner with the benefits broker to review trends, monitor utilization and claims data, and support renewal strategy
- Manage leave of absence programs (in partnership with HRBPs), including:
- FMLA
- ADA accommodations
- State-specific leaves
- Parental leave
while ensuring compliance with federal, state, and local requirements
- Complete compliance work such as:
- CMS reporting
- Non-Discrimination Testing
- HCSO calculations
- ACA reporting
- Partner with an external audit firm to complete annual 401(k) audits
- Create employee-facing benefits communications for open enrollment, onboarding, and year-round updates
- Run the annual benefits survey, summarize results, and recommend improvements
- Document internal benefits processes for consistent operations
- Support day-to-day benefits administration and escalations with confidentiality and strong service
- Partner with Accounting/Finance on plan expense tracking and invoice review
- Maintain accurate benefits collateral and new hire guides (summaries, plan details, benefits guide)
- Partner with the Workday team to configure enrollment workflows, improve processes, troubleshoot issues, and support renewals
- Provide ad hoc reporting, project support, and data analysis as needed
What You Need
- 5+ years in Benefits & Leave Administration, including 401(k) plan support
- Experience supporting or managing self-funded/self-insured health plans (required)
- Experience working in a distributed, multi-state company (required)
- Strong leave expertise (FMLA, disability, parental leave, etc.)
- Workday benefits module experience strongly preferred; ability to configure/fix processes is a plus
- Bachelor’s degree or equivalent experience
- Intermediate Excel skills (VLOOKUPs, IF formulas, etc.)
- Strong analytical, problem-solving, and organizational skills
- Strong cross-functional communication and partnership skills (HR, legal, accounting, IT, etc.)
- High confidentiality and customer-service mindset with prompt follow-through
- Bonus: Certified Benefits Professional (or similar certification)
Benefits
- Competitive salary plus company equity (RSUs)
- 401(k) with up to 4% company match
- Medical, dental, and vision options
- Life insurance, short- and long-term disability, and EAP
- Optional benefits (accident, hospital indemnity, critical illness, legal assistance, pet insurance)
- Flexible PTO for exempt employees (typically 15–20 days/year) plus 8 company-observed holidays
- Paid parental leave: up to 14 weeks (birthing) and 8 weeks (non-birthing) at 100% pay
- Continuing education and professional development opportunities
This one has a near-term deadline—apply before January 29, 2026 at 11:00 PM CST.
If you’re ready to own benefits end-to-end and build cleaner systems, better comms, and a smoother employee experience, this role is a strong fit.
Happy Hunting,
~Two Chicks…