Manager, Benefits and Compliance

The Manager of Benefits and Compliance is a strategic and hands-on leader who researches, vets, and brings forward recommendations on Evergreen's benefits, compliance, and payroll operations. This role plays a critical part in advancing Evergreen's self-funded health plan strategy, leading the optimization of the company's captive participation and related partnerships with vendors such as the benefits broker, HCM vendor, and other external partners.

This position brings deep expertise in self-funded and captive benefits strategy, vendor management, and HR compliance, ensuring programs are designed, administered, and communicated effectively while aligning with Evergreen’s culture, values, and fiscal goals.

This is a true player-coach role: strategic enough to shape long-term program direction and cost governance, and hands-on enough to execute day-to-day. Approximately 75% of the role is focused on benefits strategy, analytics, compliance, and vendor management. The remaining 25% provides final-level payroll oversight — conducting quality review, and managing escalations in partnership with Evergreen’s dedicated payroll team member.

This leader embodies Evergreen’s values—Care Personally, Extend Grace, Be Responsive, Take Ownership, Be Transparent, and Innovate—and contributes to our mission of creating authentic partnerships that improve healthcare.

WHAT YOU’LL DO

Benefits Strategy & Captive Leadership

• Lead Evergreen’s benefits strategy and ongoing transition into the self-funded Captive model, serving as the primary internal subject matter expert and liaison with captive partners.
• Partner with Leadership, Finance, and Evergreen’s benefits broker to design, evaluate, and recommend innovative benefits solutions that balance competitiveness, cost efficiency, and employee well-being.
• Conduct claims data analysis and trend reporting to identify cost drivers, utilization patterns, and opportunities for plan optimization.
• Develop cost models and plan design recommendations, presenting data-driven insights to leadership on contribution strategy, risk management, and funding performance.
• Evaluate and support carve-out programs and pilot initiatives (e.g., Donor Program, Carrot) to enhance benefit offerings and manage total plan cost.
• Oversee plan renewals, claims reporting, funding performance, and vendor deliverables for medical, dental, vision, disability, life, and voluntary benefits.
• Monitor and analyze trends in healthcare and benefits administration to anticipate future needs and support long-term strategic planning.

Compliance & Policy Governance

• Guide Evergreen’s HR compliance programs, including FMLA, ADA, ACA, ERISA, COBRA, HIPAA, and Section 125.
• Maintain responsibility for the HR compliance calendar, ensuring timely completion of audits, filings, and nondiscrimination testing.
• Lead updates to Evergreen’s employee handbook, HR policies, and benefits documentation to ensure legal compliance and alignment with company culture.
• Partner with Finance and external auditors on required reports, including 5500 filings and other annual compliance submissions.

Vendor Relationship Management

• Serve as Evergreen’s primary point of contact for third-party partners, including Hausmann Group, OSV, and captive service providers.
• Manage ongoing vendor relationships, contract reviews, renewals, and service-level expectations.
• Partner closely with the Workday System Administrator to maintain accuracy and reliability in benefits data, file feeds, and integrations with OSV and other benefit administrators.
• Collaborate with Finance and HR leadership to align vendor deliverables with Evergreen’s operational, compliance, and employee experience goals.

Payroll Oversight

• Serve as the primary final-level reviewer for payroll processing, providing a control layer to ensure accuracy and compliance before payroll is finalized.
• Conduct quality review of payroll outputs, flagging discrepancies and partnering with the payroll specialist to resolve issues in a timely manner.
• Partner with the payroll team member to support payroll-related system accuracy, integrations, and process improvements.
• Support the ongoing transition of payroll operations within HR, contributing to documentation, training, and continuous improvement efforts.

Leadership and People Management

• Develop and maintain a strong team by fostering positive relationships, leveraging individual strengths, celebrating accomplishments, and providing meaningful feedback while embracing opportunities for improvement.
• Conduct regular team meetings to unify communication, expectations, policies, procedures, and escalations, and provide relevant company updates.
• Hold weekly one-on-one meetings with team members to discuss job satisfaction, performance, growth opportunities, ongoing projects, individual/team goals, and other important topics.
• Oversee new employee onboarding, performance management, and career development, providing coaching, mentorship, and support for continuous professional development.
• Ensure employees understand and execute their duties within defined deadlines, delegating responsibilities as needed and ensuring adherence to legal and organizational policies and procedures.
• Provide clear direction, set performance expectations, conduct regular performance reviews, and identify and address skills gaps.
• Foster a positive and inclusive work environment, promoting employee engagement, well-being, collaboration, innovation, and accountability.

General

• Uphold Evergreen’s mission (Create authentic partnerships that improve healthcare) and values (Care Personally, Extend Grace, Be Responsive, Take Ownership, Be Transparent, Innovate).
• Cultivate meaningful relationships across Evergreen and with external partners.
• Embrace radical candor by developing relationships across Evergreen and providing direct feedback and recognition at all levels.
• Communicate in meetings, one-on-ones, and daily interactions with clarity, purpose, and respect for the individuals involved in the discussion.
• Participate in or lead cross-functional projects.
• Coordinate and support company-wide programs and special projects.
• Serve as subject matter expert for your team and role.
• Support colleagues and Evergreen’s growth by participating in hiring, onboarding, ongoing training, and other duties as assigned.
• Participate in the development, documentation, and improvement of processes, procedures, and policies, in alignment with Evergreen’s mission and values.
• Assist and back up other colleagues when necessary.
• Embrace change as Evergreen scales systems and processes.
• Attend Evergreen’s in-person annual retreat one time per year.

WHAT YOU’LL NEED

Qualifications

• 7 years of progressive HR experience, including at least 3 years in benefits leadership or total rewards management.
• Self-funded and captive benefits experience is required. Candidates without this background will not be considered.
• Demonstrated experience with claims data analysis, cost modeling, and plan design strategy.
• Experience managing HR vendor partnerships, including benefits brokers, TPAs, and payroll/benefit administrators.
• Familiarity with payroll processes and a comfort level providing oversight, review, and escalation support.
• Strong understanding of HR compliance regulations, including ACA, ERISA, HIPAA, FMLA, COBRA, and Section 125.
• High attention to detail, strong analytical skills, and the ability to manage multiple priorities with precision.
• Excellent interpersonal skills and sound judgment when managing sensitive and confidential information.
• Advanced proficiency in Microsoft 365 tools and HRIS platforms (Workday & OSV preferred).

OTHER DUTIES

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.