Benefits Operations Manager

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.

• 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.

• 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.

• 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.

• 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.

• 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.

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.

The company is an Equal Opportunity Employer. As an employer subject to affirmative action regulations, we invite you to voluntarily provide the following demographic information. This information is used solely for compliance with government recordkeeping, reporting, and other legal requirements. Providing this information is voluntary and refusal to do so will not affect your application status. This data will be kept separate from your application and will not be used in the hiring decision.

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