Benefits Manager

The Chicago School of Professional Psychology

1d•$105,000 - $115,000•Remote

About The Position

The Community Solution Education System seeks an experienced and strategic Benefits Manager to oversee, administer, and continuously enhance the organization’s employee benefits and leave programs, including healthcare, retirement, wellness, and leave administration (FMLA, ADA, Workers’ Compensation, STD, LTD, and related leave programs). This position plays a critical role in ensuring employees have a positive and supported experience throughout the benefits lifecycle while maintaining operational excellence, compliance, and effective vendor performance. The Benefits Manager serves as a key functional role responsible for assessing and improving benefit programs, optimizing Workday benefits functionality, strengthening employee education and engagement, and ensuring transparency and collaboration across Payroll, HR Operations, HRIS, Finance, Legal, and institutional stakeholders. This role requires a strong understanding of benefits administration processes, systems integration, leave management, vendor oversight, implementation management, change adoption, regulatory compliance, and employee support within a multifaceted and evolving organizational environment. This position reports directly to the CHRO. About The Community Solution Education System, a Collaborative Framework for Educational Excellence The Community Solution Education System (The Community Solution), founded in 2009, is a pioneering collaborative network of higher education institutions. Its defining characteristic is its commitment to “systemness;” a strategic coordination of multiple components that creates a synergistic whole greater than the sum of its parts. Saybrook University's future is inextricably linked to its continued participation in The Community Solution and its commitment to systemness. This collaboration empowers the institution to evolve and adapt, broadening accessibility, and creating innovative programs responsive to the evolving needs of its students and the global community. Through its partnership with The Community Solution, Saybrook is not just improving its own institution, but actively contributing to a transformative model for higher education that prioritizes collaboration, efficiency, and shared success. For more information, please visit The Community Solution Education System. Working Within a Systemness Model As a centralized function within The Community Solution Education System, the Benefits Manager plays a highly collaborative and enterprise-facing role supporting employees and institutional partners across the System Office and six affiliated colleges and universities. This position operates at the intersection of strategy, service, compliance, and operational partnership — helping to ensure that benefit programs are delivered consistently, effectively, and responsively across a diverse higher education environment. The Benefits Manager works closely with HR leaders and operational partners at each institution to support a unified employee experience while also recognizing the unique operational needs and cultures of individual universities. Through this collaborative model, the role contributes to the broader mission of “systemness” — leveraging shared expertise, coordinated infrastructure, and cross-functional partnership to strengthen institutional effectiveness, enhance employee support, and advance operational excellence across the entire System. This position offers a unique opportunity to work within a dynamic and evolving higher education enterprise where collaboration, continuous improvement, innovation, and shared success are highly valued.

Requirements

Strong knowledge of federal, state, and local benefits and leave regulations, including ACA, COBRA, HIPAA, ERISA, FMLA, ADA, Workers’ Compensation, STD, LTD, and related compliance requirements.
Demonstrated understanding of benefits administration operations, process improvement, systems integration, and employee support models.
Strong proficiency with Workday Benefits administration and related HR systems functionality.
Ability to assess and improve operational workflows, documentation, and employee experience related to benefits administration.
Experience managing vendor relationships, service delivery expectations, and implementation efforts.
Strong analytical, organizational, communication, problem-solving, and project management skills.
Ability to collaborate cross-functionally with Payroll, HR Operations, HRIS, Finance, Legal, managers, and external vendors.
Ability to manage sensitive and confidential information with professionalism and discretion.
Bachelor’s degree in Human Resources, Business Administration, or related field required.
Minimum of 5 years of progressive experience in benefits administration and leave management, including healthcare, retirement, and complex leave programs.
Experience administering and optimizing HRIS Benefits functionality and related HR systems, with experience in Workday preferred.
Experience managing benefits compliance activities, audits, reporting, and regulatory administration.
Experience leading benefits implementations, vendor transitions, process improvements, or operational enhancement initiatives preferred.

Nice To Haves

CEBS, SHRM-CP/SHRM-SCP, PHR/SPHR, or related certification preferred.
Experience in higher education, multi-state environments, or complex organizational structures preferred.

Responsibilities

Oversee and manage the day-to-day administration of healthcare, retirement, wellness, and leave benefit programs.
Serve as a subject matter expert for employee benefits and leave processes, ensuring employees receive accurate, timely, and supportive guidance.
Evaluate the employee experience related to benefits programs and identify opportunities to improve communication, accessibility, education, and utilization.
Develop and maintain educational resources, training materials, FAQs, and employee communications regarding benefits offerings and processes.
Lead annual benefits renewals, open enrollment processes, and employee education campaigns.
Ensure benefit programs align with organizational objectives, employee needs, and operational capabilities.
Partner closely with HR leadership, including the HR AVPs, to align benefits strategies, employee communications, wellness initiatives, and leave programs with broader employee engagement, employee experience, and workforce support objectives across The Community Solution Education System.
Oversee and support leave administration processes, including FMLA, ADA accommodations, Workers’ Compensation, STD, LTD, and other federal, state, and local leave requirements.
Partner closely with HR, Payroll, managers, and third-party administrators to ensure accurate and timely leave coordination, pay impacts, and employee communications.
Ensure compliance with all applicable federal, state, and local laws and regulations related to employee benefits administration, including ACA, COBRA, HIPAA, ERISA, Section 125 plans, retirement plan requirements, and applicable reporting obligations.
Monitor regulatory changes and proactively assess organizational impacts, recommending updates to programs, processes, communications, and policies as needed.
Support and coordinate benefits-related audits, filings, documentation, and compliance reporting requirements in partnership with internal stakeholders and external vendors.
Ensure benefit plan documentation, employee notices, disclosures, and communications are maintained and distributed in accordance with regulatory requirements and organizational standards.
Partner with vendors, brokers, Payroll, HR Operations, and Legal to ensure benefit administration practices remain compliant, operationally effective, and aligned with organizational policies.
Identify and mitigate compliance risks related to benefits administration, eligibility, enrollment, deductions, reporting, and vendor processes.
Assess current benefits and leave administration processes to identify operational gaps, inefficiencies, and opportunities for enhancement.
Develop standardized processes, documentation, and workflows to improve consistency, transparency, and accountability across the organization.
Promote operational ownership and process understanding across HR Operations and institutional stakeholders.
Collaborate cross-functionally with Payroll, HR Operations, HRIS, Finance, and other departments to ensure alignment and seamless administration of benefits and leave-related activities.
Ensure benefit-related operational processes are clearly documented, communicated, and maintained.
Serve as the lead functional resource for Workday Benefits administration and related system functionality.
Partner with HRIS and IT teams to maximize utilization of Workday benefits functionality, reporting, integrations, automation, and employee self-service capabilities.
Identify and implement opportunities to improve data accuracy, workflow efficiency, reporting capabilities, and system integration.
Support testing, configuration review, audits, and enhancement efforts related to benefits and leave administration within Workday.
Develop and maintain strong partnerships with benefit carriers, brokers, leave administrators, and third-party vendors.
Monitor vendor performance, service delivery, employee experience outcomes, and contractual obligations to ensure vendors are effectively supporting organizational and employee needs.
Escalate operational concerns and partner with vendors to resolve service, process, or compliance issues.
Lead implementation and change adoption efforts for new benefit programs, vendors, and service offerings from planning and rollout through post-implementation assessment and continuous improvement.
Partner with vendors and internal stakeholders to ensure effective communication, operational readiness, system integration, and employee education related to new or changing benefit offerings.
Evaluate program effectiveness, employee experience, and vendor performance following implementation, identifying opportunities for enhancement and process improvement.
Generate and analyze reports related to benefits utilization, enrollment trends, leave activity, employee engagement, operational effectiveness, and program costs.
Utilize data and employee feedback to identify trends, recommend improvements, and support strategic decision-making.
Support leadership with reporting, compliance documentation, audits, and recommendations related to benefits strategy and operational effectiveness.
Stay informed on emerging trends, regulations, best practices, and technology advancements related to benefits and leave administration.
Participate in professional development opportunities to maintain subject matter expertise.
Support a culture of service, transparency, operational excellence, and continuous improvement across the HR function.