Benefits Operations Manager

HighLevel

3d•$108,000 - $130,000•Remote

About The Position

HighLevel is seeking a Benefits Operations Manager to act as the operational engine for the People organization's health, foundational care, and regulatory infrastructure. This senior individual contributor role reports to the Chief of Staff in the CPO's Office and is responsible for translating strategic vision into disciplined, compliant execution. The ideal candidate is a technical compliance and benefits specialist with a deep understanding of structural implications, who prioritizes the internal customer experience and can balance rigorous documentation with a fluid, seamless system design for a fast-paced, high-growth environment.

Requirements

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.
In-depth professional knowledge and acumen regarding US health care infrastructure, ERISA rules, 401k fiduciary practices, and multi-state compliance.
Proven ability to independently evaluate variable factors, select appropriate methods, and make definitive structural recommendations that align with departmental objectives.
Proven ability to partner with and influence cross-functional groups (Legal, Finance, Accounting) by thoroughly understanding their unique constraints and shared risk goals.
A track record of measuring success by plan utilization, employee stability, and compliance health rather than just basic execution.
Exceptional judgment and complete confidentiality when handling sensitive employee scenarios, including medical leaves, personal leaves, and health-related accommodation requests.

Responsibilities

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.
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.
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.
Guide the development of new infrastructure and apply existing principles in resourceful and effective ways to navigate complex structural goals.
Treat every benefits open enrollment, wellness program, and lifestyle perk as a product launch where the employees and managers are the end users.
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.
Design, oversee, and optimize regional and global employee leave programs, ensuring an empathetic, smooth, and highly organized journey for employees taking time away.
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).
Independently research, process, and track state-by-state hiring approvals and regional compliance parameters, partnering closely with Accounting, Finance, and Legal.
Proactively identify and remove "friction points" in benefits enrollment or compliance tracking to ensure a seamless experience for the organization.
Maintain the absolute "source of truth" for all benefit records, compliance logs, and 401k updates, ensuring documentation is precise, accessible, and professional.
Build documentation standards and project rituals for compliance and leave tracking that provide maximum visibility with minimum "process tax" for managers.
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.
Translate highly technical, complex compliance parameters, legal parameters, or benefit summary descriptions into concise, human-centric narratives for executive and all-company audiences.
Proactively identify potential roadblocks to employee benefits adoption or manager compliance, designing mitigation strategies that prioritize a positive employee experience.
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.
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.
Proactively audit and identify opportunities to improve benefits administration process efficiency and compliance scalability as the enterprise grows.