Benefits Administrator

Exceptional employee experiences don't happen by accident—they're powered by thoughtful, reliable people operations. At Ledgebrook, we're hiring a Benefits Administrator to help ensure our employees are supported through every stage of their journey with us. 

This is an opportunity to play a key role within our growing People team, serving as the primary point of contact for employee benefits while supporting critical global payroll processes. You'll help employees navigate benefits programs, partner with external vendors, coordinate enrollments and life event changes, and ensure our payroll operations remain accurate and efficient. We're looking for someone who has experience administering employee benefits, understands payroll fundamentals, and enjoys helping employees navigate complex people operations processes in a fast-paced, growing environment.

In return, you'll gain exposure to a fast-growing startup environment and have the opportunity to help build and improve the people processes that support our expanding team. If you enjoy solving problems, managing complex processes, and making a meaningful impact on employees' day-to-day experience, this role offers an opportunity to grow alongside an ambitious company and People team.

Ledgebrook is a tech-enabled E&S MGA on a mission to modernize specialty insurance. The industry is burdened with legacy technology and inefficient processes that limit innovation at scale—we're changing that. Our goal is to become a best-in-class, full-stack insurance and re/insurer, leveraging AI and data-driven insights to transform underwriting, pricing, and risk selection.

What You'll Do

• Administer employee benefit programs, including medical, dental, vision, life insurance, disability, HSA/FSA, 401(k), and voluntary benefits.
• Manage benefit enrollments, qualifying life events, terminations, and annual open enrollment activities.
• Maintain accurate employee benefit records, payroll deductions, and eligibility data within Rippling.
• Serve as the primary point of contact for employee benefits questions, carrier issues, and claims escalations.
• Partner with brokers, carriers, and vendors to support benefit administration, renewals, and issue resolution.
• Support benefits compliance activities, including ACA reporting, COBRA administration, audits, and required employee notices.
• Reconcile carrier invoices, maintain documentation, and assist with benefits reporting and data analysis.
• Identify opportunities to improve benefits processes, employee experience, and operational efficiency.
• Provide backup payroll support as needed, including assisting with payroll processing, reviewing prorated deductions, and validating STD, LTD, and leave-related pay calculations.
• Support additional People Operations initiatives and projects as needed.

• 3+ years of employee benefits administration experience.
• Strong knowledge of state leave & disability insurance programs.
• Experience working with Rippling HRIS and payroll system.
• Strong understanding of benefits compliance requirements.
• Excellent attention to detail and organizational skills.
• Strong written and verbal communication skills.
• Ability to handle sensitive and confidential information with discretion.

• Experience in a startup or high-growth environment.
• SHRM-CP, PHR, CEBS, or related certification.

Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer visa sponsorship at this time