Senior Manager – Healthcare, Retirement Benefits

Role Overview

• Own the design, administration, and continuous improvement of all employee benefit programs, including medical, dental, vision, life, disability, EAP, wellness, and commuter benefits.
• Serve as the internal subject matter expert on benefits strategy, including plan design, cost drivers, and market positioning.
• Own recommendations and outcomes for benefits decisions, applying sound judgment to balance cost, compliance, employee experience, and operational complexity.
• Partner with HR leadership and Finance on renewal strategy, vendor selection, and long-term planning.
• Lead administration and oversight of the organization’s 401(k), 403(b), and 457 plans.
• Serve as the primary liaison to retirement plan advisors and recordkeepers.
• Coordinate plan audits, compliance testing, Form 5500 preparation, and required notices.
• Prepare materials and insights for retirement plan committee meetings and executive review.
• Act as the primary point of contact for all benefit vendors, brokers, and consultants.
• Set clear expectations and hold external partners accountable for performance, service quality, and deliverables.
• Evaluate vendor effectiveness and address issues or escalations as needed to ensure timely, accurate service.
• Partner closely with Finance on billing reconciliation, accruals, forecasting, and audit support.
• Translate complex benefits topics into clear recommendations and employee-facing communications.
• Lead open enrollment planning and execution, including system configuration, communications, and post-enrollment review.
• Ensure all benefit programs comply with applicable federal, state, and local regulations.
• Represent the organization confidently in audits, reviews, and executive discussions related to benefits and retirement plans.
• Monitor legislative and regulatory changes and recommend necessary updates.
• Maintain accurate documentation, SOPs, and internal controls related to benefits administration.
• Establish clear processes and guardrails to scale benefits operations reliably, reducing reliance on manual and individual handling.
• Ensure knowledge, decisions, and workflows are shared and accessible, with self-service as the default wherever possible.

Requirements

• 8+ years of progressive benefits experience, including hands-on administration of both healthcare and retirement plans, preferably in complex or multi-entity organizations.
• Demonstrated experience working directly with brokers, advisors, and senior leaders.
• Strong working knowledge of benefits compliance, audits, and retirement plan governance.
• Proven ability to operate independently, manage multiple priorities, and bring structure to complex programs.
• High comfort level partnering with Finance and navigating detailed, data-driven discussions.
• Excellent written and verbal communication skills.
• CEBS, CBP, PHR, SPHR, or related certification preferred.
• Experience leading or supporting benefits strategy through periods of organizational change preferred.

Benefits

• Competitive and affordable Medical (including hearing & hardware coverage!)
• Dental
• Vision
• Disability
• Life Insurance
• Parental Leave & Paid Compassion Leave
• Employment Assistance Program (EAP) via Spring Health
• Mental Wellness Program, including six free therapy sessions per year
• Physical Wellness Reimbursement Program
• $25/month
• Student Loan Contribution Program
• $50/month
• Pet Insurance Discount Program