Benefits Manager

Uncommon Schools is a nonprofit network of high-performing public charter schools dedicated to providing an exceptional K-12 education in economically disadvantaged communities. Operating in Boston, Camden, New York City, Newark, and Rochester, we are committed to closing the college completion gap and preparing every student for college and beyond. Our students consistently exceed national benchmarks, reflecting our dedication to their success. We invest deeply in our educators, offering weekly coaching, feedback, and professional development to ensure excellence in teaching and leadership. Join us to work hard, do good, and make a lasting difference!

The Benefits Manager is responsible for the strategic oversight, administration, and continuous improvement of the organization’s benefits and wellness programs. Reporting to the Director of HR, Benefits this role manages the full lifecycle of employee benefits, including plan design recommendations, vendor management, compliance, communications, and benefits-related data integrity. The Benefits Manager leads the benefits billing and reconciliation processes and ensures a compliant, equitable, and employee-focused experience across all benefit offerings.

As a subject matter expert in benefits administration, the Benefits Manager partners cross-functionally with Payroll, HRIS, Workday, and Data Governance teams to ensure accurate and timely benefits data management and reporting. This role also plays a key role in analyzing trends, evaluating program effectiveness, and supporting total rewards strategies that align with organizational goals.

The Benefits Manager directly supervises the Benefits Coordinator and is responsible for coaching, performance management, and professional development to ensure operational excellence and high-quality service delivery.

Duties & Responsibilities:

Employee Support

• Provides high-level guidance to employees regarding health insurance benefits, supplemental benefits, and plan changes, ensuring complex inquiries are resolved with a focus on accuracy and service.
• Serves as the primary liaison between employees, benefit carriers, brokers, and third-party administrators to resolve escalated issues, oversee contribution adjustments, refunds, and administrative updates.
• Ensures consistent communication strategies are in place to support employee understanding of benefit offerings throughout the year.

Strategic and Operational Administration of Benefits

• Oversees the administration of health, welfare, and wellness benefit programs to ensure compliance with company policies, plan documents, and applicable laws and regulations (ERISA, HIPAA, ACA, etc.).
• Leads the planning and execution of open enrollment, including project timelines, employee communications, system updates, and post-enrollment audits.
• Partners with the Director of HR, Benefits to assess benefit plan design and recommend enhancements based on employee feedback, benchmarking data, and cost analysis.
• Manages vendor relationships including to ensure service level expectations are met.
• Provides strategic oversight of benefits billing, reconciliation, and payroll integration processes in partnership with Payroll, Accounting, and HR Systems teams.
• Serves as the escalation point for benefits-related issues and leads resolution in collaboration with internal stakeholders.

Benefits Data Management & Compliance

• Oversees benefits data integrity across HRIS (WORKDAY) and vendor platforms, ensuring accurate enrollment, deductions, and eligibility across all systems.
• Leads audits of benefit transactions, vendor integrations, and data feeds, implementing
• corrections and continuous process improvements.
• Designs and leads audits and corrective communications in partnership with stakeholders.
• Collaborates with HR Systems and IT to evaluate and improve benefits-related workflows and business processes; implements enhancements to improve efficiency and compliance.
• Owns annual ACA reporting process, including data collection, vendor coordination, and regulatory filing aligned with W-2 processing.
• Maintains in-depth knowledge of federal and state benefit regulations and ensures organizational compliance.

Employee Training and Communication

• Develops and delivers benefits training and presentations to employees and managers during onboarding, open enrollment, and throughout the plan year.
• Leads the development of benefits communication strategies, ensuring employees are well-informed and engaged in utilizing available programs.
• Maintains and updates employee-facing materials and HR knowledge library related to benefits and wellness programs.

Leadership and Management

• Directly supervises one team member (Benefits Coordinator), providing coaching, feedback, and professional development opportunities to build capacity and ensure operational excellence.
• Guides and reviews the work of contract or temporary staff supporting benefits-related projects as needed.
• Collaborates with other HR leaders to align benefits administration with broader talent, compensation, and wellness strategies.

Other Responsibilities

• Leads or contributes to benefits-related special projects, including wellness initiatives, vendor RFPs, and year-end compliance testing.
• Partners with external brokers and consultants to analyze benefit trends, benchmark data, and emerging market practices.
• Proactively monitors legislative and regulatory changes and advises HR leadership on required adjustments and strategic impacts.

•  

• BA required; SHRM certification preferred, but not required
• 5-7 years of progressively responsible experience in employee benefits administration, with at least 2 years in a role with supervisory, project leadership, or strategic oversight responsibilities; 3 years of direct Benefits experience
• Exceptional interpersonal, communication, and presentation skills, with the ability to convey complex benefit concepts clearly and persuasively to diverse audiences, including staff, leadership, and external partners.
• Proven organizational and project management skills; ability to manage multiple priorities and deadlines with a strategic and proactive approach.
• Strong client service orientation with the ability to collaborate and build effective relationships across all levels of the organization, including with vendors and external consultants.
• Demonstrated ability to thrive in a dynamic, fast-paced, and evolving environment, with a focus on continuous improvement and process optimization.
• Deep knowledge of health, welfare, and wellness benefit plan structures, regulations, and best practices.
• High level of discretion, judgment, and professionalism in handling sensitive employee information and business matters.
• Strong leadership skills with experience supervising, coaching, and developing team members or junior staff.
• Analytical mindset with strong attention to detail and the ability to identify trends, solve complex problems, and support data-driven decision-making.
• Solid understanding of federal and state employment laws and regulations related to employee benefits, including ACA, HIPAA, ERISA, and COBRA.
• Working knowledge of state-specific benefits laws in New York, New Jersey, and Massachusetts is a plus.
• Proficient in benefits administration and configuration within Workday or a similar HRIS platform; able to troubleshoot system issues and support process enhancements.
• Skilled in Microsoft Office and Google Workspace tools; strong Excel/Sheets capabilities for benefits data management and reporting
• Willingness to travel to our schools across five regions as needed to support employee engagement and leadership collaboration.

Our people are what make us Uncommon. We offer competitive compensation and comprehensive benefits that support the personal health, wellness, and finances of our staff and their families. Our compensation philosophy values equity & fairness and attracting & retaining top talent. [same for all roles]

Compensation 

Compensation for this role is between $91,300 to $107,400. 

Starting pay is determined using various factors including but not limited to relevant professional experience, education, certifications, and tenure with Uncommon Schools. If you meet all job description requirements you will likely receive an offer of $96,700. 

Benefits

• 19 days of paid time off
• 3 weeks of paid Winter and Summer org-wide holidays
• Comprehensive Health, Dental, and Vision insurance plans
• 403(b) retirement savings program + employer match
• Paid leave of absence options (parental, medical, disability, etc.)
• Mental health and counseling support + wellness benefits
• Pre-tax flexible spending, dependent care, and health saving accounts

*A detailed list of all benefits is located HERE.

At Uncommon, we believe that a supportive and welcoming environment helps our students, staff, and community thrive. We are dedicated to building a team that brings a wide range of perspectives and experiences, reflective of the communities we serve---with over 70% of our staff identifying as people of color. Our organization values respect and open dialogue on important topics that shape our school culture.

As an equal opportunity employer, Uncommon provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. We also ensure that individuals with disabilities receive all privileges and benefits associated with employment and are provided reasonable accommodations for the interview process and to perform core job functions. If you would like to request an accommodation, please email [email protected].