Benefits Operations Manager

HighLevel

2d•$105,000 - $132,000•Remote

About The Position

HighLevel is seeking a Benefits Operations Manager to own the delivery, optimization, and ongoing evolution of its benefits programs. Reporting to the Chief of Staff in the CPO’s Office, this senior individual contributor will ensure the benefits experience is accurate, scalable, employee-centered, and operationally strong. The role owns day-to-day U.S. benefits operations while contributing to the company’s global benefits philosophy. It includes strengthening vendor performance, improving service delivery, and building the processes, education, and infrastructure employees need to understand and use their benefits. The ideal candidate brings deep benefits expertise, sound operational judgment, a customer-first mindset, and a continuous-improvement orientation, and can work across strategy and execution in a fast-growing, globally distributed organization. HighLevel is an AI-powered business operating system serving agencies, entrepreneurs, and small and midsize businesses. The company has more than 2,000 team members across 10+ countries and operates as a global, remote-first organization. This position is based in the USA and is remote. The stated annual salary range is $105,000–$132,000.

Requirements

At least 8 years of progressive experience in U.S. benefits administration and operations, including ownership of complex programs, renewals, vendor relationships, and employee escalations.
Strong knowledge of U.S. health and welfare benefits, ERISA, ACA, COBRA, Section 125, HSA/FSA administration, and 401(k) operations.
Ability to evaluate complex issues, identify root causes, weigh tradeoffs, and make practical recommendations balancing employee experience, cost, risk, and scalability.
Experience managing brokers, carriers, and benefits vendors and partnering with Finance, Payroll, Legal, People Operations, and People Technology.
Experience improving benefits processes, controls, integrations, and service models rather than relying on manual workarounds.
Strong spreadsheet and data-analysis skills, including the ability to interpret cost, utilization, enrollment accuracy, invoice variance, ticket trends, and vendor performance.
Ability to communicate complex benefits information clearly to employees and provide concise recommendations to leaders.
Exceptional judgment and confidentiality when handling sensitive benefits, health, and employee information.
Ability to work independently in a fast-moving, globally distributed environment and create structure while processes are evolving.

Responsibilities

Own day-to-day U.S. health benefits administration, including medical, dental, vision, life, FSA/HSA, 401(k), EAP, enrollments, qualified life events, terminations, COBRA, eligibility changes, and employee escalations.
Manage benefits ticket intake, resolution, escalations, and trend analysis to improve service and reduce recurring issues.
Manage relationships with brokers, carriers, administrators, and benefits vendors, including performance, service levels, escalations, and ongoing improvement.
Partner with the Chief of Staff to develop and evolve the global benefits philosophy, evaluating programs across countries and employee populations for competitiveness, consistency, cost, and employee experience.
Lead a year-round global benefits education program that helps employees understand and use their benefits effectively.
Build, launch, and manage employee perks and well-being programs aligned with the company’s benefits philosophy.
Design benefits programs, communications, and service experiences that are intuitive, accessible, and easy for employees and managers to navigate.
Maintain clear benefits documentation, controls, ownership, and source-of-truth records so processes are accurate, repeatable, auditable, and easy to operate.
Continuously improve benefits programs, vendors, processes, systems, and employee experience using data, feedback, and performance trends.
Translate complex benefits topics into clear recommendations for leaders and practical, human-centered guidance for employees.