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.

Required

• 6–10+ years of progressive benefits administration experience, with demonstrated ability to manage a full benefits program independently.
• Hands-on experience with health and welfare plan administration, retirement programs, and leave management.
• Proficiency with benefits administration platforms and HRIS systems (ADP, Workday, Dayforce, or equivalent), including carrier file feed management.
• Working knowledge of ERISA, ACA, COBRA, HIPAA, FMLA, and state leave regulations.
• Strong Excel skills for data analysis, audit reconciliation, and reporting.
• Exceptional attention to detail and ability to manage sensitive personal and financial data with absolute discretion.
• Self-directed and comfortable operating in a lean, fast-paced, high-trust environment.

Preferred

• Experience in a family office, private wealth, or similarly lean and confidential environment.
• Prior involvement in benefits platform implementation or open enrollment system configuration.
• Exposure to global or multi-jurisdiction benefits programs.
• CEBS, PHR, SPHR, SHRM-CP, or SHRM-SCP designation.

Base Salary

The base salary for this position ranges from $120,000 to $130,000 annually, depending on overall experience, qualifications, and performance throughout the interview process. This base salary is only one component of the total compensation package.

Benefits

• Medical, dental, and vision coverage for employees and eligible dependents
• 401(k)
• Health Savings Account (HSA)
• Life insurance
• Paid time off
• Laptop reimbursement
• New starter package to purchase hardware essentials (monitor, headphones, and other equipment)
• Learning & Development opportunities

Equal Opportunity

We value diversity and always treat all employees and job applicants based on merit, qualifications, competence, and talent. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by applicable law.