Senior Benefits Analyst for the Hoskinson Family Office

As a Senior Benefits Analyst, you will own the day-to-day execution of onboarding, benefits administration, and the data integrity that the company depends on. This is a focused benefits hire for a lean, family office. As the Senior Benefits Analyst, you will be an in-house expert for all health, welfare, retirement, and leave programs. You'll own the full benefits lifecycle from strategy and compliance through vendor management, systems accuracy, and employee support. You will partner with the Head of Human Resources and HFO Leadership to ensure the program is competitive, compliant, and running with precision.

Key Responsibilities

Benefits Program Administration

• Administer all U.S. health and welfare and retirement programs (medical, dental, vision, life, disability, FSA/HSA, 401(k)), including eligibility processing, enrollment, plan changes, and life events.
• Serve as the primary point of contact for all employee benefits inquiries, resolving issues with accuracy and discretion.
• Manage carrier EDI file feeds and payroll integrations, monitoring transmissions and resolving interface discrepancies to ensure enrollment and funding accuracy.
• Perform routine audits of eligibility files, payroll deductions, and vendor databases to maintain alignment with internal HRIS records.
• Coordinate absence and leave administration, partnering with third-party administrators to ensure accurate processing of FMLA, ADA, STD, and LTD transactions.

Compliance & Regulatory Oversight

• Ensure compliance with ERISA, ACA, COBRA, HIPAA, FMLA, and applicable state regulations, maintaining audit-ready documentation at all times.
• Manage government filings and compliance reporting, including Form 5500, ACA 1094-C/1095-C, PCORI, and required participant notices.
• Monitor regulatory changes and assess their impact on plan design and operations, briefing leadership and proactively implementing required updates.
• Prepare and maintain compliance documentation to support internal reviews, audits, and government submissions.

Annual Open Enrollment

• Lead the annual open enrollment cycle from start to finish, including system configuration and testing, employee communications, enrollment support, and post-enrollment auditing.
• Develop clear, accessible enrollment materials and decision-support resources to help employees make informed benefit elections.
• Validate all enrollment data and payroll deductions following open enrollment to ensure accuracy before the first payroll cycle.

Vendor & Broker Management

• Manage day-to-day relationships with brokers, carriers, and third-party administrators, holding vendors accountable to service standards and contractual commitments.
• Support the annual renewal process by gathering and analyzing plan performance data, benchmarking against the market, and preparing summary recommendations for leadership review.
• Participate in implementation and plan update projects, coordinating with vendors and internal stakeholders through testing and go-live.

Reporting & Process Improvement

• Generate standard and ad hoc reports from HRIS and vendor systems to support operational decisions and compliance reviews.
• Identify data trends or inconsistencies and escalate findings to leadership with recommended corrective actions.
• Maintain and improve SOPs and process documentation to drive accuracy, efficiency, and audit readiness.
• Recommend enhancements to benefits processes and the overall employee experience as the family office continues to evolve.