Employee Benefits Sales Executive

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

About The Position

What You’ll Do Build and grow a profitable Employee Benefits book of business through consultative, relationship-based selling Develop trusted advisor relationships with business owners, HR leaders, and executive decision-makers Prospect strategically through networking, referrals, centers of influence, and targeted outreach Deliver customized benefit strategies across medical, dental, vision, life, disability, and ancillary lines Lead client conversations around plan design, cost containment, compliance, and employee engagement Collaborate closely with internal service, analytics, and consulting teams to deliver a high-touch client experience Represent R&R in the marketplace as a knowledgeable, credible Employee Benefits expert What Sets You Apart Experience selling Employee Benefits in an agency, brokerage, or consulting environment Strong sales instincts paired with a consultative, relationship-first approach Ability to communicate complex benefit concepts in a clear, confident, and credible way Entrepreneurial mindset with the discipline to build and manage a long-term book of business Proven ability to prospect, influence, and close while maintaining trust and integrity Active Life & Health insurance license required Why Join R&R? True Independence: One of the largest independently owned agencies in the Midwest, family-led since 1975 Real Sales Support: Experienced service and consulting teams handle the day-to-day, freeing you up to do what you do best—build relationships and grow revenue. Elite Market Access: Broad carrier relationships and resources that elevate your credibility in the market Uncapped Earning Potential: Competitive base salary plus commission, with earnings driven by your success Stability You Can Build On: Long-term thinking, consistent leadership, and reinvestment in people and tools Award-Winning Culture: Recognized as a Top 100 Independent Agency, Milwaukee Journal Sentinel's Best Places to Work and Healthiest Employer Growth-Focused Environment: Mentorship, collaboration, and career paths that support experienced producers About R&R Insurance R&R Insurance is proudly family-led, Midwest-rooted, and driven by a mission to deliver peace of mind through service, integrity, and expertise. Our award-winning team continues to grow because of our commitment to clients and to each other. Join the Knowledge Broker Team and start your next chapter with an agency built for the long run. Apply today.

Requirements

Experience selling Employee Benefits in an agency, brokerage, or consulting environment
Strong sales instincts paired with a consultative, relationship-first approach
Ability to communicate complex benefit concepts in a clear, confident, and credible way
Entrepreneurial mindset with the discipline to build and manage a long-term book of business
Proven ability to prospect, influence, and close while maintaining trust and integrity
Active Life & Health insurance license required

Responsibilities

Build and grow a profitable Employee Benefits book of business through consultative, relationship-based selling
Develop trusted advisor relationships with business owners, HR leaders, and executive decision-makers
Prospect strategically through networking, referrals, centers of influence, and targeted outreach
Deliver customized benefit strategies across medical, dental, vision, life, disability, and ancillary lines
Lead client conversations around plan design, cost containment, compliance, and employee engagement
Collaborate closely with internal service, analytics, and consulting teams to deliver a high-touch client experience
Represent R&R in the marketplace as a knowledgeable, credible Employee Benefits expert