Sr. Director, Health Plan and Benefits
The Wonderful Company
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Los Angeles, CA
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Mid-Senior level
Posted April 3, 2026
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Responsibilities
Commitments
Responsibilities
- 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.
Commitments
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.
24/7 online physician consultations
library of on-demand fitness videos
Continuous Improvement Training: Participate in training that empowers all employees to learn and implement concepts that drive significant, positive change in the workplace.
1 mandarin orange in America; POM Wonderful® is the No.
1 100% pomegranate brand in America; FIJI® Water is America’s No.
1 premium imported bottled water brand; JUSTIN® Wine has the No.
Not Met Priorities
What still needs stronger evidence
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.
- Experience leading benefits programs through large‑scale change, technology implementations, or M&A strongly 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.
Preferred Skills
- Advanced certifications (CEBS, CBP, SPHR) a plus.
- Experience leading benefits programs through large‑scale change, technology implementations, or M&A strongly preferred.
Education
- (Not required) – Bachelor’s degree in Human Resources, Business, Finance, or a related discipline preferred.
- (Not required) – Advanced certifications (CEBS, CBP, SPHR) a plus.
Company Description
You may know us as FIJI Water, POM Wonderful, Justin Wine, Teleflora and Halos Citrus, but we’re all Wonderful – and we have a great opportunity for a Sr. Director, Health Plan and Benefits. 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.
Job Description
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.
Qualifications
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.
Advanced certifications (CEBS, CBP, SPHR) a plus.
Experience leading benefits programs through large‑scale change, technology implementations, or M&A strongly 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.
Salary: $220,000-$260,000 and may include a discretionary bonus. Final compensation will be dependent upon skills & experience.
Additional Information
Thriving Wellness Community: 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
Career Advancement Opportunities: Unlock your potential with clear paths for career progression and internal mobility across our diverse family of brands and business units.
Focused Learning and Development: 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.
Empowering Mentorship Program: Connect with colleagues through our company-wide mentorship program to share goals, overcome challenges, and drive your career forward.
Continuous Improvement Training: Participate in training that empowers all employees to learn and implement concepts that drive significant, positive change in the workplace.
Building a Healthy Society: To date, our co-Founders Lynda and Stewart Resnick, through their foundations and The Wonderful Company, have invested more than $2.5 billion in education, health and wellness, community development, and sustainability initiatives across California’s Central Valley, Fiji, and the world. In 2025, Wonderful ranked as #1 in PEOPLE’s “100 Companies That Care” list and was named one of Fortune magazine’s 100 Best Companies to Work For. To learn more about our corporate social responsibility efforts, visit csr.wonderful.com.
Giving Back to the Community: 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.
Headquartered in Los Angeles, The Wonderful Company is a privately held $6 billion company dedicated to harvesting health around the world through its iconic consumer brands. The company’s 10,000 employees worldwide are committed to bringing consumers everywhere the freshest, most wholesome pistachios, citrus and pomegranates; bottling the finest water and wines; and creating colorful bouquets that are sure to touch the heart. This commitment is reflected in the company’s market share: Wonderful Pistachios® is America’s No. 1 tree nut and America’s fastest-growing snack; Wonderful® Halos® is the No. 1 mandarin orange in America; POM Wonderful® is the No. 1 100% pomegranate brand in America; FIJI® Water is America’s No. 1 premium imported bottled water brand; JUSTIN® Wine has the No. 1 Cabernet Sauvignon in California; and Teleflora® is the world’s leading floral delivery service.
The Wonderful Company’s connection to consumers has health at its heart and giving back at its core. The company has a long-standing commitment to corporate social responsibility, including more than $1 billion invested in environmental sustainability; $65 million in charitable giving, education initiatives, and innovative health and wellness programs each year; and $143 million toward the construction of two charter school campuses in California’s Central Valley. To view the current Corporate Social Responsibility report, visit www.wonderful.com/csr.
To learn more about The Wonderful Company, its products and its core values, visit www.wonderful.com, or follow us on Facebook, Twitter and Instagram.
The Wonderful Company is an Equality Opportunity Employer that provides opportunities for advancement. We are committed to creating a diverse workforce that embodies a deep culture of acceptance, equity, and inclusion. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, protected veteran status, or other protected categories.
EEO is the law - click here for more information
You may know us as FIJI Water, POM Wonderful, Justin Wine, Teleflora and Halos Citrus, but we’re all Wonderful – and we have a great opportunity for a Sr. Director, Health Plan and Benefits. 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.
Job Description
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.
Qualifications
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.
Advanced certifications (CEBS, CBP, SPHR) a plus.
Experience leading benefits programs through large‑scale change, technology implementations, or M&A strongly 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.
Salary: $220,000-$260,000 and may include a discretionary bonus. Final compensation will be dependent upon skills & experience.
Additional Information
Thriving Wellness Community: 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
Career Advancement Opportunities: Unlock your potential with clear paths for career progression and internal mobility across our diverse family of brands and business units.
Focused Learning and Development: 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.
Empowering Mentorship Program: Connect with colleagues through our company-wide mentorship program to share goals, overcome challenges, and drive your career forward.
Continuous Improvement Training: Participate in training that empowers all employees to learn and implement concepts that drive significant, positive change in the workplace.
Building a Healthy Society: To date, our co-Founders Lynda and Stewart Resnick, through their foundations and The Wonderful Company, have invested more than $2.5 billion in education, health and wellness, community development, and sustainability initiatives across California’s Central Valley, Fiji, and the world. In 2025, Wonderful ranked as #1 in PEOPLE’s “100 Companies That Care” list and was named one of Fortune magazine’s 100 Best Companies to Work For. To learn more about our corporate social responsibility efforts, visit csr.wonderful.com.
Giving Back to the Community: 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.
Headquartered in Los Angeles, The Wonderful Company is a privately held $6 billion company dedicated to harvesting health around the world through its iconic consumer brands. The company’s 10,000 employees worldwide are committed to bringing consumers everywhere the freshest, most wholesome pistachios, citrus and pomegranates; bottling the finest water and wines; and creating colorful bouquets that are sure to touch the heart. This commitment is reflected in the company’s market share: Wonderful Pistachios® is America’s No. 1 tree nut and America’s fastest-growing snack; Wonderful® Halos® is the No. 1 mandarin orange in America; POM Wonderful® is the No. 1 100% pomegranate brand in America; FIJI® Water is America’s No. 1 premium imported bottled water brand; JUSTIN® Wine has the No. 1 Cabernet Sauvignon in California; and Teleflora® is the world’s leading floral delivery service.
The Wonderful Company’s connection to consumers has health at its heart and giving back at its core. The company has a long-standing commitment to corporate social responsibility, including more than $1 billion invested in environmental sustainability; $65 million in charitable giving, education initiatives, and innovative health and wellness programs each year; and $143 million toward the construction of two charter school campuses in California’s Central Valley. To view the current Corporate Social Responsibility report, visit www.wonderful.com/csr.
To learn more about The Wonderful Company, its products and its core values, visit www.wonderful.com, or follow us on Facebook, Twitter and Instagram.
The Wonderful Company is an Equality Opportunity Employer that provides opportunities for advancement. We are committed to creating a diverse workforce that embodies a deep culture of acceptance, equity, and inclusion. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, protected veteran status, or other protected categories.
EEO is the law - click here for more information