Benefits Manager

Can you turn benefits complexity into clarity and recurring problems into better processes? 

You’re comfortable asking a broker a difficult question, tracing a discrepancy to its source, and bringing leadership a well-supported recommendation, not just another question. You take ownership, keep the details accurate, and follow through until the issue is resolved. Just as importantly, you understand that behind every enrollment, deduction, and leave question is an employee who needs clear information and thoughtful support. 

TPS Group Holdings LLC is seeking a hands-on Benefits Manager who combines technical expertise with sound judgment and a drive to make things work better. You’ll own the day-to-day execution and continuous improvement of our benefits, leave, and wellness programs—working independently, partnering across teams, and turning complex information into practical decisions. This is an individual-contributor role at launch, with manager-level ownership and accountability: an opportunity to lead the function, stay close to the details, and build reliable processes that scale. 

Key Responsibilities 

Benefits Strategy & Program Leadership 

• Lead the year-round administration and continuous improvement of health and welfare programs, including medical, dental, vision, life, disability, voluntary benefits, and related offerings. 

• Develop data-informed recommendations on plan design, employee contributions, eligibility, funding approaches, and program enhancements for review by People & Culture leadership. 

• Monitor market developments, employee needs, utilization patterns, and business priorities to identify opportunities to improve the benefits portfolio. 

• Serve as the internal benefits subject matter expert and provide timely guidance to leaders, People & Culture partners, Payroll, HRIS, and employees. 

• Maintain a forward-looking benefits calendar, decision schedule, and risk log so annual work is planned rather than managed reactively. 

Annual Renewal & Open Enrollment 

• Lead the annual benefits renewal process from initial data collection and strategy development through final plan implementation. 

• Coordinate plan modeling, cost projections, contribution scenarios, leadership materials, approvals, and implementation activities with internal and external partners. 

• Lead open enrollment end-to-end, including project planning, system readiness, employee communications, education sessions, enrollment support, issue resolution, and post-enrollment audits. 

• Ensure plan documents, summary materials, microsite content, Paycom resources, and employee-facing communications are accurate, current, and easy to understand. 

• Partner with Payroll and HRIS to validate deductions, eligibility rules, carrier files, effective dates, and plan configuration before and after implementation. 

Vendor & Broker Management 

• Own the day-to-day relationships with benefits brokers, carriers, leave administrators, and other benefits vendors. 

• Establish service expectations, track open issues, escalate service failures, and conduct recurring vendor performance reviews. 

• Coordinate requests for data, plan documents, contracts, invoices, communications, and renewal deliverables. 

• Partner with broker to analyze program costs, enrollment, participation, utilization, billing, and operational trends; identify risks, discrepancies, and savings opportunities. 

• Partner with broker and Director of People Ops to prepare clear decision materials and recommendations for People & Culture leadership, including tradeoffs, financial impact, implementation considerations, and employee experience implications. 

Benefits Operations, Systems, & Compliance 

• Oversee accurate and timely benefits administration in Paycom, including eligibility, life events, enrollment workflows, plan configuration, employee deductions, and supporting documents. 

• Partner with HRIS and Payroll on system testing, integrations, carrier files, audits, and issue resolution. 

• Create controls and recurring audits that identify enrollment, eligibility, billing, and deduction discrepancies and drive timely correction. 

• Maintain benefits policies, plan records, required notices, and employee communications in accordance with applicable requirements and company standards. 

• Monitor regulatory developments and coordinate required changes with leadership, vendors, brokers, and legal counsel as appropriate. 

• Protect sensitive employee and health information and maintain appropriate recordkeeping and confidentiality practices. 

• Lead year-round benefits communication and education in partnership with the broker to improve employee understanding of programs, costs, eligibility, deadlines, and available support. 

• Act as a visible and credible benefits partner who balances employee needs, compliance requirements, and business realities. 

Leadership & Cross-Functional Partnership 

• Independently manage complex projects, bring forward solutions, anticipate risks, and keep stakeholders informed of decisions and dependencies. 

• Partner closely with People & Culture leadership, Payroll, HRIS, Finance, Operations, Communications, and business leaders. 

• Manage up by presenting a clear point of view, recommended course of action, alternatives considered, and issues requiring leadership decision. 

• Use AI-enabled tools and automation responsibly to improve analysis, documentation, communications, service delivery, and process efficiency. 

Qualifications 

• Bachelor’s degree in Human Resources, Business, Finance, or a related field, or equivalent relevant experience. 

• 5+ years of progressive benefits experience, including significant responsibility for benefits administration, annual renewal, open enrollment, and vendor management. 

• Demonstrated ability to independently manage a multi-location or multi-state benefits program and provide recommendations to P&C leadership. 

• Working knowledge of health and welfare plans, leave administration, benefits compliance, payroll deductions, and HRIS benefits functionality. 

• Advanced analytical, project management, problem-solving, and stakeholder-management capabilities. 

• Experience with self-funded or partially self-funded plans preferred. 

• Experience with Paycom or a comparable HRIS preferred. 

• CEBS, SHRM, HRCI, or related professional certification preferred. 

The pay range on this posting reflects what the company reasonably expects to pay for this position at this location at the time of this posting.

TPS Group Holdings is an equal-opportunity employer and considers all qualified applicants for employment without regard to race, color, national origin, religion, sex, disability, age, veteran status, or any other classification protected by state, local or federal law.