Senior Benefits Specialist

Delavan Holdings•Delavan, WI

10d•$70,000 - $80,000

About The Position

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. 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.

Requirements

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

Nice To Haves

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

Responsibilities

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
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
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
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