Sr Manager, Benefits

Colonial-Williamsburg-Foundation; Williamsburg (VA); On-site; USD 110,000 - 165,000; Full time

Job summary

Colonial Williamsburg Foundation in Williamsburg, VA seeks a senior benefits leader to oversee all aspects of the employee benefits portfolio and leave programs. The role focuses on strategic design, cost management, compliance, and vendor relations to maximize value for employees and the organization.

The position requires 7+ years in benefits with people management experience, deep knowledge of U.S. benefit programs, and proficiency with HRIS systems, including Workday.

Qualifications

• Bachelor’s degree in HR, business or related field preferred.
• Seven+ years in employee benefits with progressive responsibility.
• Two+ years of people management experience.
• Broad knowledge of U.S. employee benefits (health, retirement, leave).
• Strong compliance knowledge: ERISA, ACA, COBRA, HIPAA, FMLA, ADA.
• Experience with HRIS and benefits administration systems.

Responsibilities

• Lead, manage, and develop the benefits team including coaching and development.
• Oversee day-to-day administration of medical, dental, vision, life, disability, 401(k) and other benefits.
• Provide strategic leadership balancing costs, plan competitiveness, and organizational goals.
• Oversee leave programs including FMLA, ADA, and disability leaves.
• Manage workers’ compensation program including claims and vendor relations.
• Lead renewals, open enrollment, plan design, and vendor negotiations.
• Implement and optimize Workday Benefits module with cross‑functional partners.
• Collaborate with Finance/Payroll for funding, deductions, and reporting.
• Coordinate with HRIS to configure and administer benefits in systems.
• Monitor utilization, costs, trends, and vendor performance.
• Ensure compliance with ERISA, ACA, COBRA, HIPAA, FMLA, ADA, and state laws.
• Develop communications and educational materials for employees.
• Identify opportunities to improve processes, technology, and service delivery.
• Lead special benefits-related projects and system changes.
• Maintain confidentiality of sensitive information.

Skills

Benefits administration

Leadership

Data analytics

Communication

Education

Bachelor’s degree in HR or related field

Tools

Workday

HRIS

Job description

BRUTON HEIGHTS SCHOOL
Williamsburg, VA 23185, USA

Description

Who We Are

Founded in 1926, the Colonial Williamsburg Foundation is a private, not-for-profit educational, historic, and cultural institution that owns and operates one of the largest and best-known museum complexes in the world. Our mission is “that the future may learn from the past” through preserving and restoring 18 th -century Williamsburg, Virginia’s colonial capital. We engage, inform, and inspire people to learn about this historic capital, the events that occurred here, and the diverse peoples who helped shape a new nation.

Today, Colonial Williamsburg is the largest living history museum in the U.S. The Historic Area is the 301-acre restored colonial capital with 89 original buildings and 525 buildings reconstructed to how they appeared in the 18th century through extensive archaeological, architectural, and documentary research. The Historic Area is staffed by highly trained, historically dressed interpreters and expert tradespeople who bring the 18th century to life. The Foundation also owns and operates two world-class museums, the DeWitt Wallace Decorative Arts Museum, and the Abby Aldrich Rockefeller Folk Art Museum, The Bob and Marion Wilson Teacher Institute , and a renowned research library, the John D Rockefeller Jr Library.

Additionally, Colonial Williamsburg is home to five world class accommodations at the Williamsburg Inn, Williamsburg Lodge Autograph Collection, the Griffin Hotel, the Williamsburg Woodlands Hotels and Suites and the unique Colonial Houses in the Historical Area. Visitors may also indulge in food and drink at our many on site restaurants and taverns that blend a historically inspired dining experience with today’s evolved tastes. Each year over five million people visit Williamsburg and another 20 million engage with us digitally.

About the Position

Main Duties:

Responsibilities include but are not limited to:

• Lead, manage, and develop the benefits team, including setting priorities, allocating workloads, coaching team members, and supporting professional development.
• Oversee the day-to-day administration of the company’s full portfolio of benefit programs, including medical, dental, vision, life, disability, 401(k), pension, and other employee benefit programs.
• Provide strategic and operational leadership for benefits programs, balancing employee needs, plan competitiveness, cost management, and organizational objectives.
• Oversee the administration of leave programs, including coordination of FMLA, ADA, short- and long-term disability, and other applicable federal, state, and company leave programs.
• Oversee the company’s workers’ compensation program, including claims administration, vendor/carrier relationships, reporting, and coordination with HR and other stakeholders.
• Manage relationships with benefits brokers, carriers, third-party administrators, consultants, and other external partners.
• Lead the annual benefits renewal and open enrollment process, including plan design, vendor negotiations, communications, systems readiness, testing, and employee support.
• Lead the implementation and ongoing optimization of the Workday Benefits module, serving as the benefits subject matter expert and partnering with HRIS, IT, vendors, and cross-functional stakeholders on requirements, plan configuration, integrations, testing, data validation, deployment, and ongoing process improvements.
• Partner with Finance and Payroll to ensure accurate benefits funding, deductions, reconciliations, invoices, and financial reporting.
• Partner with HRIS to ensure benefits and leave programs are accurately configured, maintained, tested, and administered within HR systems.
• Monitor benefits utilization, costs, trends, and vendor performance and develop recommendations to improve plan effectiveness and manage costs.
• Ensure benefits programs and processes comply with applicable federal, state, and local laws and regulations, including ERISA, ACA, COBRA, HIPAA, FMLA, ADA, and other applicable requirements.
• Oversee required benefits compliance, reporting, filings, audits, and documentation.
• Establish and maintain effective benefits policies, procedures, controls, and operational processes.
• Serve as a senior subject matter expert and escalation point for complex employee benefits and leave matters.
• Develop clear and effective employee communications and educational materials to help employees understand and maximize their benefits.
• Use benefits data and analytics to identify trends, risks, and opportunities and provide insights and recommendations to HR leadership.
• Identify opportunities to improve benefits processes, technology, service delivery, and the overall employee experience.
• Lead benefits-related projects and initiatives, including system implementations, vendor transitions, plan changes, and process improvements.
• Maintain a high level of confidentiality and discretion when handling sensitive employee, medical, leave, and benefits information.

This job description reflects the general responsibilities of the position and is not intended to be an exhaustive list. Duties and responsibilities may evolve over time based on operational needs.

Required & Preferred Education and Experience:

• Bachelor’s degree in Human Resources, Business Administration, Finance, or a related field preferred.
• Seven+ years of progressive experience in employee benefits, with demonstrated experience managing comprehensive benefits programs.
• Two+ years of people management experience, with a track record of developing and leading high-performing teams.
• Broad knowledge of U.S. employee benefits, including health and welfare plans, retirement plans, life and disability programs, and leave administration.
• Strong understanding of benefits compliance and regulatory requirements, including ERISA, ACA, COBRA, HIPAA, FMLA, and ADA.
• Experience overseeing leave administration and workers’ compensation programs preferred.
• Experience managing relationships with benefits brokers, carriers, consultants, and third-party administrators.
• Strong analytical skills with the ability to evaluate plan costs, utilization, vendor performance, and other benefits data.
• Experience with HRIS and benefits administration systems, including system implementations, integrations, testing, and data validation.
• Strong project management skills and the ability to manage multiple complex programs and deadlines.
• Excellent communication and interpersonal skills, with the ability to effectively partner with employees, HR leaders, Finance, Payroll, HRIS, vendors, and senior leadership.
• Strong judgment and problem-solving skills, particularly when handling sensitive or complex employee benefits matters.
• Ability to balance strategic program management with hands‑on operational oversight in a dynamic environment.

Preferred Qualifications

• Experience managing benefits programs in a mid-sized or large organization with a diverse employee population.
• Experience with both defined contribution and defined benefit retirement plans, including 401(k) and pension administration.
• Professional benefits certification such as CEBS, SHRM-CP/SCP, or related credential.
• Experience leading benefits technology implementations or significant process transformations.

Compensation Disclaimer: The compensation listed below for this position represents the anticipated hiring range and is provided in accordance with Virginia pay transparency requirements. Actual compensation will be determined based on factors such as the selected candidate’s skills, qualifications, experience, education, certifications, internal equity, and the specific requirements of the role.

Range: $110,000 - $165,000/year

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.