Benefits Operations Manager

Reports To: Chief of Staff, CPO’s Office Location: USA (Remote) 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 shared 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. Learn more about us on our YouTube Channel or Blog Posts 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 apply 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 are the end users. Foundational Program Execution: Own the full administration of US health benefits and 401k plans, serving as the main point of contact for day-to-day vendor relationships, platform management, and system updates. Leave & Care Management: Design, oversee, and optimize regional and global employee leave programs, ensuring an empathetic, smooth, and highly organized journey for employees taking time away. Well-Being & Perks Optimization: Build out, launch, and manage modern employee perk architectures (such as remote-work stipends and lifestyle perks) alongside company-wide well-being initiatives (mental health weeks, wellness programs). Geographic Compliance Navigation: Independently research, process, and track state-by-state hiring approvals and regional compliance parameters, partnering closely with Accounting, Finance, and Legal. Design for Adoption: Proactively identify and remove "friction points" in benefits enrollment or compliance tracking to ensure a seamless experience for the organization. Quality & Process Rigor: Maintain the absolute "source of truth" for all benefit records, compliance logs, and 401k updates, ensuring documentation is precise, accessible, and professional. Agile Governance & Process Rigor Establish "Just Enough" Governance: Build documentation standards and project rituals for compliance and leave tracking that provide maximum visibility with minimum "process tax" for managers. Navigate Ambiguity with Grace: Understand and work on complex issues where analysis of situations or data requires an in-depth evaluation of variable factors. Shift gears fluidly as business footprints expand across new states, maintaining operational momentum. Clear & Empathetic Communication: Translate highly technical, complex compliance parameters, legal parameters, or benefit summary descriptions into concise, human-centric narratives for executive and all-company audiences. Enable Change & Adoption Anticipate Resistance Points: Proactively identify potential roadblocks to employee benefits adoption or manager compliance, designing mitigation strategies that prioritize a positive employee experience. Build High-Touch Enablement: Create intuitive leader toolkits, clear compliance FAQs, benefits summaries, and feedback loops that empower stakeholders to navigate health plans and leave parameters with minimal overhead. Iterate Based on Feedback: Use plan utilization data, employee feedback, and real-time sentiment data to pivot perk configurations and wellness program designs, ensuring they solve actual user problems. Identify Efficiency Opportunities: Proactively audit and identify opportunities to improve benefits administration process efficiency and compliance scalability as the enterprise grows. What You’ll Bring 8+ Years of Experience: Leading complex, multi-workstream initiatives within US health benefits administration, 401k management, and employment compliance in high-growth, remote-first environments. Advanced Wide-Ranging Expertise: In-depth professional knowledge and acumen regarding US health care infrastructure, ERISA rules, 401k fiduciary practices, and multi-state compliance. Strategic Judgment: Proven ability to independently evaluate variable factors, select appropriate methods, and make definitive structural recommendations that align with departmental objectives. Stakeholder Empathy & Influence: Proven ability to partner with and influence cross-functional groups (Legal, Finance, Accounting) by thoroughly understanding their unique constraints and shared risk goals. Outcome Over Output: A track record of measuring success by plan utilization, employee stability, and compliance health rather than just basic execution. High EQ & Discretion: Exceptional judgment and complete confidentiality when handling sensitive employee scenarios, including medical leaves, personal leaves, and health-related accommodation requests. Why This Role Matters At HighLevel, we move fast, but speed without structure leads to friction and risk. This role is the bridge between "what" we want to provide to support our team and "how" it actually gets executed sustainably and securely. By establishing agile governance, strict compliance, and process rigor across our benefits, perks, and wellness programs, you ensure that the People team’s operational foundation is sequenced correctly, resourced effectively, and delivered with excellence. You matter because you protect our culture of Customer Obsession by securing our team's foundational well-being. By managing dependencies, auditing plans, and proactively mitigating regulatory risks, you prevent administrative fatigue and ensure that every benefit plan and wellness initiative feels like a true value-add to our employees. Ultimately, you are the architect of our operational backbone, enabling the CPO’s Office to scale with precision and driving measurable impact that keeps our talent—and our business—ahead of the curve.  The salary range for this position is $108000 - $130000 annually.