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Senior Benefits Specialist

Job in Delavan, Walworth County, Wisconsin, 53115, USA
Listing for: Delavan Holdings
Full Time position
Listed on 2026-09-02
Job specializations:
  • Business
    Regulatory Compliance Specialist
Salary/Wage Range or Industry Benchmark: 70000 - 80000 USD Yearly USD 70000.00 80000.00 YEAR
Job Description & How to Apply Below

Senior Benefits Specialist

Strategic Impact | Cross-Functional Leadership | Employee Experience

Why Delavan Holdings?

The Senior Benefits Specialist plays a critical role in shaping, optimizing, and delivering Delavan Holdings' health and welfare benefit programs. This role goes beyond administration to drive strategy, improve outcomes, and influence decisions across a complex and evolving benefits landscape.

You will partner cross functionally and with external vendors to enhance the effectiveness of our programs and an elevated employee experience. This role requires both deep technical expertise and strong strategic thinking, with the ability to identify opportunities, solve complex problems, and lead change.

Position Summary

Delavan Holdings is seeking a Senior Benefits Specialist to lead strategy, compliance, and operational excellence across our health and welfare benefit programs. The ideal candidate balances deep technical expertise with strategic thinking, translating data and trends into recommendations that shape decisions across the organization.

Compensation
  • $70,000 - $80,000 based on experience
Requirements What You'll Do

Drive Strategy & Continuous Improvement

  • Identify opportunities to improve benefit programs through plan design, vendor performance, cost management, and employee experience
  • Analyze trends, issues, and data to develop recommendations and influence decision-making
  • Diagnose root causes of recurring issues and partner with subject matter experts to provide systemic, scalable solutions
  • Drive transparency around Benefits to a large and diverse population of employees
  • Challenge the status quo and bring forward innovative ideas to improve outcomes

Lead Cross-Functional Execution

  • Partner cross functionally to design and implement benefit programs aligned to Delavan Holdings' strategic priorities and values
  • Lead key initiatives such as open enrollment, compliance audits, and vendor implementations with a focus on outcomes going beyond execution
  • Influence internal and external stakeholders to drive alignment and achieve results

Ensure Compliance & Risk Management

  • Oversee compliance across ERISA and Section 125 health and welfare programs, ensuring accuracy, audit readiness, and adherence to regulatory requirements
  • Proactively identify and mitigate legal, fiduciary, and operational risks
  • Lead internal and external audits, including coordination of data requests and stakeholder alignment

Optimize Operations & Service Delivery

  • Lead day-to-day benefits operations with a focus on efficiency, accuracy, and continuous improvement
  • Manage and resolve complex escalations by addressing underlying process or system gaps
  • Ensure processes are scalable and aligned with business needs
  • Provide superior customer service to internal and external cross functional teams
Required
  • Bachelor's degree in HR, Business, or related field (or equivalent experience)
  • 5+ years of experience in Benefits, HR, or related field
  • Strong knowledge of health and welfare programs, including ERISA and Section 125 regulations
  • Demonstrated experience influencing benefit strategy, plan design, or program outcomes
  • Experience leading cross-functional initiatives and driving change across stakeholders
  • Strong analytical and problem-solving skills, with the ability to translate data into action
  • Excellent written and verbal communication and stakeholder management skills
  • Experience working with complex benefit ecosystems, including multiple vendors and technologies
What Makes You a Fit
  • Thinks beyond administration and focuses on how benefits drive business and employee outcomes
  • Uses data, trends, and insights to inform recommendations and influence decisions
  • Can translate complex issues into clear, actionable strategies for leaders
  • Proactively identifies risks and opportunities before they surface
  • Comfortable challenging the status quo to improve results
  • Balances attention to detail with the ability to see the broader system and long-term impact
Benefits

Eligible team members may receive:

  • Medical, Dental, and Vision Insurance
  • 401(k) Retirement Plan with Company Match
  • Paid Time Off
  • Life Insurance
  • Employee Assistance Program
  • Daily Pay Options
  • Employee Discounts on Vehicles, Parts, and Service
  • Ongoing Training and Professional Development, Including Annual I-CAR Training
  • Career Advancement Opportunities Throughout Kunes Auto Group
Join the Delavan Holdings Team

If you're ready to bring strategic thinking and technical expertise to a role that shapes real outcomes for employees, we'd love to hear from you.

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Position Requirements
10+ Years work experience
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