Benefits Administrator
About the Role
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.
About you
Here at Ledgebrook we’re passionate about creating a team that thrives on continuous learning and shares our excitement about building a company from the ground up. We’re looking for people to join us with:
A passion for delivering world-class customer service to our internal and external customers
Intellectual curiosity and a strong desire for innovation, rather than following the status quo
A hunger for continuous learning and opportunities to grow
Agile prioritization skills coupled with a keen sense of urgency - we balance getting it right with getting it done right now
A strong drive and desire to win together as a high-performing team
A moral compass to "do the right thing, period." We have zero tolerance for toxic behaviors
An eagerness to actively participate and connect with the whole team, across remote locations
An honest, transparent communication style
A proactive, solution-oriented mindset. We don’t look for blame, we look for the solution
Requirements
Required
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.
Preferred
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
Benefits
Full remote flexibility and asynchronous work culture
Unlimited PTO and fully paid sick leave
Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options
Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage
A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company
The chance to make a meaningful impact while working alongside an ambitious, high-performing team
Exposure to the challenges and opportunities of a fast-growing startup environment
Compensation
Base Salary Range $75,000-100,000- This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including experience, qualifications, geographic location and other relevant factors. The salary range is for a full time position but we are open to 4 days/week.
Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.
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.
About you
Here at Ledgebrook we’re passionate about creating a team that thrives on continuous learning and shares our excitement about building a company from the ground up. We’re looking for people to join us with:
A passion for delivering world-class customer service to our internal and external customers
Intellectual curiosity and a strong desire for innovation, rather than following the status quo
A hunger for continuous learning and opportunities to grow
Agile prioritization skills coupled with a keen sense of urgency - we balance getting it right with getting it done right now
A strong drive and desire to win together as a high-performing team
A moral compass to "do the right thing, period." We have zero tolerance for toxic behaviors
An eagerness to actively participate and connect with the whole team, across remote locations
An honest, transparent communication style
A proactive, solution-oriented mindset. We don’t look for blame, we look for the solution
Requirements
Required
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.
Preferred
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
Benefits
Full remote flexibility and asynchronous work culture
Unlimited PTO and fully paid sick leave
Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options
Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage
A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company
The chance to make a meaningful impact while working alongside an ambitious, high-performing team
Exposure to the challenges and opportunities of a fast-growing startup environment
Compensation
Base Salary Range $75,000-100,000- This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including experience, qualifications, geographic location and other relevant factors. The salary range is for a full time position but we are open to 4 days/week.
Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.