Benefits Operations Manager

About the Role

We’re looking for a Benefits Operations Manager to own the delivery, optimization, and continued evolution of HighLevel’s benefits programs. Reporting to the Chief of Staff in the CPO’s Office, you’ll serve as the senior individual contributor responsible for ensuring our benefits experience is accurate, scalable, employee-centered, and operationally strong.

This role goes beyond administration. You’ll own day-to-day US benefits operations while helping shape our global benefits philosophy, strengthening vendor performance, improving service delivery, and building the processes, education, and infrastructure that make benefits easier for employees to understand and use.

The ideal candidate combines deep benefits expertise with strong operational judgment, a customer-first mindset, and a continuous improvement orientation. You know how to move between strategy and execution, translate complex benefits topics into clear guidance, and build systems that can scale with a fast-growing, globally distributed company.

What You’ll Do

Foundational Program Execution: Own the full day-to-day administration of US health benefits including medical, dental, vision, life, FSA/HSA, 401(k), EAP, enrollments, qualified life events, terminations, COBRA, eligibility changes, and employee escalations.
Employee Benefits Support & Ticket Management: Own benefits ticket intake, resolution, escalation, and trend analysis to improve service and reduce repeat issues.
Vendor & Carrier Management: Own relationships with brokers, carriers, administrators, and benefits vendors, including performance, service levels, escalations, and ongoing improvement.
Global Benefits Strategy: Partner with the Chief of Staff to develop and evolve HighLevel’s global benefits philosophy, evaluating programs across countries and employee populations for competitiveness, consistency, cost, and employee experience.
Global Benefits Education & Enablement: Lead a year-round global benefits education program that helps employees understand and use their benefits effectively.
Well-Being & Perks Optimization: Build, launch, and manage employee perks and well-being programs aligned with HighLevel’s overall benefits philosophy.
Design for Employee Experience: Design benefits programs, communications, and service experiences that are intuitive, accessible, and easy for employees and managers to navigate.
Quality & Process Rigor: Maintain clear benefits documentation, controls, ownership, and source-of-truth records so processes are accurate, repeatable, auditable, and easy to operate.
Continuous Improvement & Program Optimization: Continuously improve the overall benefits program, vendors, processes, systems, and employee experience using data, feedback, and performance trends.
Executive & Employee Communication: Translate complex benefits topics into clear recommendations for leaders and simple, human-centered guidance for employees.

What You’ll Bring

8+ Years of Benefits Experience: Progressive experience in US benefits administration and operations, including ownership of complex programs, renewals, vendor relationships, and employee escalations.
Deep Benefits Expertise: Strong knowledge of US health and welfare benefits, ERISA, ACA, COBRA, Section 125, HSA/FSA administration, and 401(k) operations.
Strategic & Operational Judgment: Proven ability to evaluate complex issues, identify root causes, weigh tradeoffs, and make practical recommendations that balance employee experience, cost, risk, and scalability.
Vendor & Stakeholder Leadership: Strong experience managing brokers, carriers, and benefits vendors while partnering effectively with Finance, Payroll, Legal, People Operations, and People Technology.
Systems & Process Mindset: Experience improving benefits processes, controls, integrations, and service models rather than relying on manual workarounds.
Builder Mindset: You’re energized by fixing what’s broken, building processes and infrastructure from the ground up, and leaving programs stronger, clearer, and more scalable than you found them.
Fast Learner & Collaborative Operator: You absorb context quickly, ask thoughtful questions, and can begin contributing from day one while building strong partnerships across internal teams and external vendors.
Analytical Capability: Strong spreadsheet and data-analysis skills with the ability to interpret cost, utilization, enrollment accuracy, invoice variance, ticket trends, and vendor performance.
Employee-Centered Communication: Ability to translate complex benefits information into clear, practical guidance for employees and concise recommendations for leaders.
Continuous Improvement Orientation: A track record of using data, feedback, and operational trends to improve programs, vendors, processes, and employee experience over time.
High EQ & Discretion: Exceptional judgment and confidentiality when handling sensitive benefits, health, and employee information.
Comfort in Ambiguity: Ability to operate independently in a fast-moving, globally distributed environment and create structure where processes are still evolving.