Sr Benefit Analyst

R&R Insurance and Wealth Management Career • Waukesha, WI

1d

About The Position

Are you the person who actually enjoys digging into the numbers? The one who sees trends others miss and turns raw data into real strategy? R&R Insurance is looking for a Senior Benefits Analyst to support our growing Employee Benefits practice. This role is ideal for someone who thrives in financial modeling, understands both self-funded and fully insured plan structures, and wants to play a meaningful role in shaping client strategy. You won’t just crunch numbers. You’ll influence renewal strategies, support producers with data-backed insights, and help clients make confident, informed decisions.

Requirements

• Associate’s degree required; Bachelor’s degree in Actuarial Science, Risk Management, Mathematics, Statistics, or a related analytical field preferred
• 5+ years of insurance agency experience (or at least 2 years with R&R Insurance)
• Strong experience with self-funded and fully insured benefit plan analysis
• Advanced proficiency in Microsoft Office
• Experience with Applied Benefits Designer, Claros Analytics, and/or BenefitPoint preferred
• Active Health & Life License (or ability to obtain within 90 days)
• Proven ability to manage multiple projects in a fast-paced environment with exceptional accuracy
• Strong written and verbal communication skills, including professional correspondence
• Demonstrated ability to proactively identify and solve complex problems
• You are self-driven, collaborative, and detail-oriented.
• You take ownership.
• You anticipate issues before they arise.
• And you enjoy continuously sharpening your expertise.

Nice To Haves

• Bachelor’s degree in Actuarial Science, Risk Management, Mathematics, Statistics, or a related analytical field preferred
• Experience with Applied Benefits Designer, Claros Analytics, and/or BenefitPoint

Responsibilities

• Financial Modeling & Analysis Prepare the financial components of client and prospect presentations
• Model claims and cost projections for self-funded plans, including stop-loss deductible evaluations
• Review and analyze fully insured renewals and funding scenarios
• Identify trends in utilization data and translate findings into actionable recommendations
• Strategic Partnership Support producers in evaluating plan design, funding strategy, and contribution recommendations
• Participate in financial discussions that impact client decision-making
• Stay current on market shifts, carrier strategy changes, and product innovations
• Technology & Data Management Build and maintain databases within Applied Benefits Designer and Claros Analytics
• Leverage reporting systems to produce accurate, meaningful insights
• Maintain high-level accuracy and organization across multiple client projects

Benefits

• Independence that puts people first – No private equity, no Wall Street pressure, no short-term thinking
• Supportive leadership that invests in your development
• Best-in-class benefits , including a 37.5-hour workweek and Flex scheduling after 60 days
• Award-winning culture where teamwork, integrity, and innovation thrive
• Real opportunities to grow , with leaders who promote from within

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: Associate degree