Sr. Director, Health Plan and Benefits

The Wonderful Company • Los Angeles, CA

15d • $220,000 - $260,000 • Hybrid

About The Position

We’re looking to make the world a healthier place through an uncompromising commitment to the well-being of our employees and their families. We foster a collaborative workforce that encourages an entrepreneurial spirit and openness to change. The Sr. Director, Health Plan and Benefits serves as the strategic leader responsible for the design, delivery, governance, and continuous improvement of The Wonderful Company’s benefits and wellness programs, including a large, complex self funded health plan covering more than 10,000 members as well global policies for employees in 25+ countries. We operate an innovative model for employees and families in California’s Central Valley built around a network of integrated primary care clinics and are constantly evaluating ways to further expand this model. This leader ensures programs are financially sustainable, market competitive, operationally excellent, and aligned with business goals, employee needs, and organizational values. This role drives strategy across a diverse set of businesses and acts as a trusted advisor to executives. The Sr. Director partners closely with the Chief Medical Officer, Total Rewards leadership, HR, IT, Payroll, and external partners to optimize plan performance, enhance employee experience, and strengthen our ability to attract and retain top talent. This position will be based at our West Los Angeles, CA office. We work a hybrid schedule with an in-office requirement Monday-Wednesday and the option to work remotely on Thursday and Friday.

Requirements

• 10–15+ years of progressive experience in benefits, including at least 5+ years leading a benefits function for an organization with 5,000+ employees.
• Experience overseeing a self‑funded health plan is required.
• Experience with direct contracting with hospitals is required.
• Bachelor’s degree in Human Resources, Business, Finance, or a related discipline preferred.
• Deep expertise in benefits design, self‑funded plan management, ERISA, ACA, and other regulatory frameworks.
• Strong financial acumen with the ability to model scenarios, manage large budgets, and interpret complex healthcare data.
• Executive presence with ability to influence senior leadership and drive enterprise‑wide decisions.
• Proven capability to negotiate complex vendor contracts and manage high‑value vendor relationships.
• Highly collaborative, with strong communication and interpersonal skills across diverse teams.
• Strategic thinker who can operate both at the vision level and with hands‑on execution.
• Ability to thrive in a fast‑paced, dynamic environment with changing priorities.
• Ability to attract and recruit top talent, motivate the team, delegate effectively, celebrate diversity within the team, and manage performance; widely viewed as a strong developer of others.
• A leader who is self-reflective and aware of their own limitations; leads by example and drives the organization's performance with an attitude of continuous improvement by being open to feedback and self-improvement.

Nice To Haves

• Advanced certifications (CEBS, CBP, SPHR) a plus.
• Experience leading benefits programs through large‑scale change, technology implementations, or M&A strongly preferred.

Responsibilities

• Benefits Strategy & Program Leadership Lead strategy, design, implementation, and ongoing management of all employee benefit programs, including medical, dental, vision, pharmacy, life, disability, wellness, and other ancillary benefits.
• Drive innovation in healthcare delivery and benefits offerings, including evaluating and implementing direct contracting opportunities with providers in key regions.
• Develop and execute a multi‑year benefits strategy that aligns with organizational goals, cost‑management strategies, and employee value propositions.
• Manage global benefits for our international employees in 25+ countries
• Partner with the Chief Medical Officer to evaluate population health trends and make data‑driven recommendations.
• Financial Management & Cost Stewardship Own the financial strategy and performance of the self‑funded health plans, including budgeting, forecasting, reserve analysis, and annual rate setting.
• Conduct financial modeling for health plan initiatives, wellness programs, vendor proposals, and plan design changes.
• Evaluate and recommend funding strategies such as stop‑loss optimization, captives, and alternative risk arrangements.
• Governance, Compliance & Risk Management Lead fiduciary oversight activities and adherence to ERISA requirements.
• Manage plan documentation, including Summary Plan Descriptions, amendments, SBCs, 1095‑C reporting, and annual Form 5500 filings.
• Oversee compliance with federal, state, and local benefits laws (such as: ACA, HIPAA, COBRA, FMLA, Section 125, MHPAEA, etc.).
• Maintain audit readiness and mitigate compliance risks through proactive monitoring and internal controls.
• Vendor, Broker & Partner Management Lead vendor strategy, including selection, negotiation, performance management, and continuous improvement across carriers, TPAs, PBMs, wellness vendors, and consultants.
• Conduct and manage RFPs for major programs ensuring service quality, cost competitiveness, and alignment with benefit strategy.
• Establish and monitor vendor SLAs, KPIs, and scorecards to ensure high‑quality service delivery.
• Benefits Technology & Operations Oversee benefits administration platforms, HRIS integrations, and related systems to ensure accurate, efficient, and user‑friendly employee experience.
• Lead the Open Enrollment process, including system configuration, testing, communications, and post‑implementation analysis.
• Evaluate and implement new technologies.
• Employee Experience, Communications & Change Management Lead comprehensive benefits communication strategies that ensure clarity, accessibility, and high engagement across diverse employee populations.
• Develop manager and employee training, educational materials, and year‑round communication campaigns.
• Ensure programs support health equity, inclusion, and accessibility.
• Wellness & Population Health Management Develop and execute wellness strategies that improve preventive care, chronic condition management, mental health accessibility, and behavioral health support.
• Partner with the Chief Medical Officer and data teams to monitor health trends and improve population outcomes.
• Leadership & Team Development Lead, develop, and manage a high‑performing team with a focus on coaching, talent development, and organizational effectiveness.
• Foster a culture of collaboration, continuous improvement, and operational excellence.

Benefits

• Access to top-notch medical coverage comprehensive vision and dental plans, and a 401k with match eligibility to secure your financial future and including: 24/7 online physician consultations virtual mental health resources life coaching engaging employee community groups cash rewards for healthy habits and fitness reimbursements library of on-demand fitness videos
• Unlock your potential with clear paths for career progression and internal mobility across our diverse family of brands and business units.
• Grow as a leader with our dedicated Learning and Organizational Development department, offering extensive resources like People Manager and leadership training, webinars, and eLearning courses.
• Connect with colleagues through our company-wide mentorship program to share goals, overcome challenges, and drive your career forward.
• Participate in training that empowers all employees to learn and implement concepts that drive significant, positive change in the workplace.
• Make a difference with Wonderful Giving , allowing you to allocate company-provided funds to up to three charities of your choice, and join Wonderful Neighbor to contribute to group service projects within our local communities.

What This Job Offers

• Job Type: Full-time
• Career Level: Director