Benefits Operations Manager

About us HighLevel is an AI-powered business operating system that gives agencies, entrepreneurs and SMBs the infrastructure to build, automate and scale. Today, HighLevel supports SMBs across 150+ countries, fueling community-driven growth rooted in real customer outcomes. To date, businesses operating on HighLevel have generated over $7 billion in ecosystem value, demonstrating the impact of d infrastructure at scale. By centralizing conversations, automation and intelligence into one system, we help businesses move faster, reduce complexity and execute efficiently. Behind the platform, HighLevel powers more than 4 billion API hits and 2.5 billion message events daily. With 250 terabytes of distributed data, 250+ microservices and over 1 million domain names supported, our architecture is built for performance, resilience and long-term scalability. Our people With over 2,000 team members across 10+ countries, HighLevel operates as a global, remote-first organization built for speed and ownership. We value initiative, clarity and execution, creating space for ambitious people to build systems that support millions of businesses worldwide. Here, innovation thrives, ideas are celebrated and people come first, no matter where they call home. Our impact Every month, HighLevel enables more than 1.5 billion messages, 200 million leads and 20 million conversations for the more than 1 million businesses we support. Behind those numbers are real people building independence, expanding opportunity and creating measurable impact. We’re proud to be a part of that. About the Role We’re looking for a Benefits Operations Manager to serve as the agile "engine room" for the health, foundational care, and regulatory infrastructure of the People organization at HighLevel. Reporting directly to the Chief of Staff in the CPO’s Office, you will lead high-impact initiatives dedicated to translating strategic vision into disciplined, compliant execution. This isn't a "check-the-box" administrative role; it is a senior individual contributor position designed for a technical compliance and benefits specialist who thrives on solving complex, cross-functional puzzles. As a seasoned professional, you possess specialized or advanced expertise and will work on assignments requiring considerable judgment and initiative, understanding the deep structural implications of your work and making independent recommendations for solutions. The ideal candidate is obsessed with the internal customer experience, viewing every benefit option, leave policy, wellness program, and state-by-state approval framework through the lens of the employee and manager. You must be a master of "just enough" governance: providing the rigorous documentation and compliance needed for corporate security while designing systems that are fluid and seamless for our fast-paced, high-growth environment. What You’ll Do - End-to-End Initiative Lifecycle Ownership - Drive Cross-Functional Delivery: Own the full lifecycle of high-visibility benefits, wellness, and compliance initiatives, from initial concept and framework chartering to final multi-state implementation and employee adoption. - Manage Team-Wide Sequencing: Partner with the Chief of Staff to prioritize the compliance and benefits collective backlog, ensuring resources are focused on high-priority regulatory and infrastructure needs. - Rapid Re-Scoping: Demonstrate the agility to shift program goals, wellness rollouts, and plan timelines mid-stream as business priorities or federal/state regulations evolve, without losing operational rigor. - Direct Application of Principles: Guide the development of new infrastructure and existing principles in resourceful and effective ways to navigate complex structural goals. - Customer-Obsessed Governance & Execution - Adopt a "Customer First" Mindset: Treat every benefits open enrollment, wellness program, and lifestyle perk as a product launch where the employees and managers a