Senior Benefits Analyst

The Crosby Company is a family office responsible for wealth management and preservation for multiple branches and generations of a single family. The Crosby Company provides middle and back office services to various individual businesses including Curatorial, Foundations, Investments, Trust, Tax and Private Real Estate.

The Senior Benefits Analyst plays a key role in the design, administration, and analysis of employee benefits programs. This position ensures compliance with regulatory requirements, supports strategic benefits initiatives, and provides expert guidance to employees and HR partners. The ideal candidate is detail-oriented, analytical, and passionate about enhancing the employee’s experience through impactful benefits offerings.

• Support the day-to-day operations of health, welfare, retirement, and voluntary benefit programs.
• Manage and coordinate all leave programs including state and federal programs
• Serve as a subject matter expert for the benefits of policies, procedures, and systems.
• Manage vendor relationships and ensure service level agreements are met.
• Support and manage wellness related activities and events

• Analyze benefits utilization, cost trends, and employee engagement metrics.
• Prepare regular reports for leadership and support annual budgeting and forecasting.

• Ensure compliance with federal, state, and local regulations (e.g., ERISA, ACA, HIPAA).
• Support audits and filings, including Form 5500 and nondiscrimination testing.
• Maintain accurate documentation and records for all benefit plans.

• Respond to complex employee inquiries and resolve escalated issues.
• Develop and deliver benefits of education materials and presentations.
• Support open enrollment planning and execution.

• Lead or support benefits-related projects, including system implementations and policy updates.
• Collaborate with cross-functional teams to improve processes and employee experience.

• Bachelor's degree in human resources management, Business Administration, or related field preferred
• 7+ years of experience in employee benefits administration or HR analytics.
• Strong knowledge of benefits regulations and compliance requirements.
• Proficiency in HRIS systems and data analysis tools (e.g., Excel, Power BI).
• Excellent communication, problem-solving, and organizational skills.
• CEBS or other benefits related certification preferred.
• Detail-oriented with strong critical thinking skills
• Proficient in Microsoft Office suite and HRIS systems (ADP preferred)
• Familiar with benefits laws and regulations (ACA, COBRA, ERISA, HIPAA, FMLA)
• Comfortable with and adept at learning new technology interfaces and software packages
• Strong time management, organizational, and prioritization skills.
• High attention to detail and accuracy.
• Excellent interpersonal, written, and verbal communication skills with all levels of the organization
• Initiative-taking, positive attitude, highly motivated, self-directed and with minimal daily supervision
• Demonstrated flexibility in adapting to new and varying situations

The Crosby Company of New Hampshire is an equal opportunity employer. We believe that the most effective way to attract, develop, and retain a diverse workforce is to build an enduring culture of inclusion and belonging.