Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Employee Benefits Sales Executive

R&R Insurance and Wealth Management

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.

Equal Opportunity Employer


This employer is required to notify all applicants of their rights pursuant to federal employment laws.
For further information, please review the Know Your Rights notice from the Department of Labor.
Vacancy posted 3 days ago
Similar jobs that could be interesting for youBased on the Employee Benefits Sales Executive in Waukesha, WI vacancy
  •  ...Employee Benefits Sales Executive 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... 
    Suggested
    Base plus commission

    Wausau Insurance

    Waukesha, WI
    3 days ago
  • Alliant Insurance Services is seeking a qualified candidate for a role focused on management and advanced pricing analysis in their Employee Benefits Department. Responsibilities include leading underwriting teams, managing client projects, and ensuring the accuracy of... 
    Suggested
    Work at office

    Alliant Insurance Services

    Pewaukee, WI
    11 hours ago
  • Overview R&R Insurance is growing, and our Employee Benefits team is looking for an Employee Benefits Analyst who enjoys working with data, solving problems, and helping clients understand the financial side of their benefit plans. Responsibilities Prepare monthly benefits... 
    Suggested
    Work at office
    Flexible hours

    SupportFinity

    Waukesha, WI
    1 day ago
  • $44.7k - $71.3k

    Join to apply for the Employee Benefits Analyst role at Marsh McLennan Agency 1 day ago Be among the first 25 applicants Join to apply for the Employee Benefits Analyst role at Marsh McLennan Agency Our not-so-secret sauce. Award-winning, inclusive, Top Workplace culture... 
    Suggested
    Minimum wage
    Full time
    Part time
    Work at office
    Local area
    Work from home
    Relocation package
    Night shift

    Marsh McLennan Agency

    Waukesha, WI
    4 days ago
  • Acrisure, LLC is seeking a Senior Employee Benefits Account Executive to enhance client relationships and oversee employee benefits strategies. This role involves mentoring a team and coordinating benefit communications, with an emphasis on compliance and industry standards... 
    Suggested

    Acrisure, LLC

    New Berlin, WI
    3 days ago
  • SupportFinity™ in Waukesha, Wisconsin is looking for an Employee Benefits Analyst to join their growing team. This role involves preparing benefits claims reports, developing analyses for clients, and assisting with financial presentations. The ideal candidate will hold... 

    SupportFinity

    Waukesha, WI
    11 hours ago
  • ## Senior Employee Benefits Account Executive## Acrisure is a global Fintech leader that combines the best of humans and high tech to offer multiple financial...  ...a professional insurance advisor, and facilitating the sales cycle of identified opportunities to achieve client... 
    Immediate start
    Flexible hours

    Acrisure LLC

    New Berlin, WI
    5 days ago
  •  ...on what makes us the best broker in the business. As Employee Benefits Consultant you'll be responsible for demonstrating that...  ...retain new clients for the Agency. Strategic Sales Focus: Create and execute an aggressive sales marketing plan to achieve established... 
    Full time
    Work at office
    Monday to Friday
    Flexible hours

    The Hausmann Group

    Waukesha, WI
    1 day ago
  • $80k - $120k

     ...environment that strategically positions our employees for longevity and success. At HUB, we...  ...you with competitive and flexible benefits options that are rooted in your current...  ...handled by Account Administrator or Account Executive Manages new carrier, plan, or vendor... 
    Contract work
    Local area
    Flexible hours

    Squaremouth

    Waukesha, WI
    3 days ago
  • R&R Wealth Management, LLC in Waukesha, Wisconsin, is looking for an experienced Employee Benefits sales professional to build and manage a lucrative book of business. The ideal candidate will develop trusted relationships with business owners and HR leaders while delivering... 

    R&R Wealth Management, LLC

    Waukesha, WI
    4 days ago
  •  ...Please read the application process completely. As a Student Employee, you will gain valuable professional experience while...  ...week (depending on position). * Student employees are not benefit eligible. M inimum Qualifications * Be enrolled as a current... 
    Internship
    Flexible hours

    Waukesha County Technical College

    Pewaukee, WI
    4 days ago
  •  ...technical and administrative support to the Account Representatives, Sales Representatives, and Regional Vice President for the assigned...  ..., associates, staff, and the community. Enjoy a competitive benefits package including: ~401(k) with a Company Match ~ Access to... 

    National Insurance Services

    Brookfield, WI
    4 days ago
  •  ...RESPONSIBILITY LEVEL: The Employee Experience Manager (EEM) is responsible for overseeing...  ...driving store productivity, and ensuring sales and margin targets are met. This role...  ...to compensation, we offer a competitive benefit program that may include medical, dental,... 
    Full time
    Temporary work
    Part time
    Flexible hours
    Shift work
    Night shift
    Weekend work

    Goodwill Industries of Southeastern Wisconsin, Inc.

    Waukesha, WI
    3 days ago
  •  ...technology provider in Wisconsin is looking for an IT Sales Consultant. This position involves generating leads,...  ...excellent communication skills. The company offers extensive benefits including health insurance, an employee ownership plan, and uncapped commissions, focused on... 
    Work at office

    MSI Metro Sales

    Menomonee Falls, WI
    3 days ago
  •  ...Employee Health & Benefits Consultant Sales Award-winning, inclusive, Top Workplace culture doesn't happen overnight. It's a result of hard work by...  ...consultative sales approach, and conduct proposals to C-Level Executives. Our future colleague. We'd love to meet you if... 
    Work at office
    Local area
    Night shift

    Oliver Wyman, LLC

    Brookfield, WI
    11 hours ago
  •  ...This role involves managing complex HR operations, supporting employee owners, and developing solutions to meet leaders' specific needs...  ...Resources. A commitment to equitable workplace practices is essential. Benefits include a collaborative work environment and professional... 

    MRA-The Management Association

    New Berlin, WI
    11 hours ago
  •  ...customer satisfaction. Successful candidates will demonstrate strong communication skills, creativity, and a commitment to outstanding customer service. Benefits include employee ownership, no-premium health coverage, and a supportive work culture. #J-18808-Ljbffr Role, Inc.

    Role, Inc.

    New Berlin, WI
    4 days ago
  •  ...ensuring quality and timely delivery of goods. The ideal candidate has 3 years of relevant experience and a bachelor's degree in a related field. Harken values innovation, craftsmanship, and offers unique benefits like an Employee Ownership Plan. #J-18808-Ljbffr Harken Inc.

    Harken Inc.

    Pewaukee, WI
    2 days ago
  • Metro Sales Inc. is looking for an Employee-Owner, IT Sales Consultant to join our team in Menomonee Falls, WI. In this role, you'll be responsible...  ...excellent communication skills. This position offers extensive benefits, including medical insurance, a 401(k) match, and an... 

    Metro Sales Inc.

    Menomonee Falls, WI
    1 day ago
  •  ...to oversee HR activities, including recruitment, training, and employee relations. The ideal candidate has a Bachelor’s degree and over...  ...Spanish are required. The role offers a competitive salary, employee benefits, and a climate-controlled work environment. #J-18808-Ljbffr... 

    Technical Metal Specialties

    New Berlin, WI
    1 day ago
  • Goodwill Greater Milwaukee & Chicago is seeking an Employee Experience Manager to enhance workforce development and maximize store productivity...  ...demonstrate strong communication and problem-solving skills. Benefits include medical, dental, and retirement plans, along with paid... 

    Goodwill Greater Milwaukee & Chicago

    Waukesha, WI
    1 day ago
  • $70k - $100k

     ...Orkin Sales Inspector If you're great at sales, we've got the career for you. Are you...  ...showcasing the value, protection, and long-term benefits of Orkin's services Manage...  ...Paid vacation, sick leave, and holidays ~ Employee stock purchase plan, tuition reimbursement... 

    HomeTeam Pest Defense

    Waukesha, WI
    4 days ago
  • $47k

     ...support to the Account Representatives, Sales Representatives, and Regional Vice President...  ..., and the community. Enjoy a competitive benefits package including: ~401(k) with a...  ...experience in customer service, preferably in an employee benefits-related capacity. Ability to... 

    National Insurance Services

    Brookfield, WI
    11 days ago
  •  ...excited to hire students for On-Campus Student Employment positions where you will develop vital professional skills. As a Student Employee, you will gain experience in customer service, communication, and workplace professionalism, all while balancing academic... 
    Flexible hours

    Waukesha County Technical College

    Pewaukee, WI
    1 day ago
  • Wenthe-Davidson Engineering Co. is looking for an HR Generalist to manage HR operations and support our dedicated employee owners. Ideal candidates will have a passion for enhancing workplace culture through effective communication and relationship building. Responsibilities... 

    Wenthe-Davidson Engineering Co.

    New Berlin, WI
    3 days ago
  • $92.6k - $121.13k

     ...involves leading operations on complex vertical concrete construction, collaborating with field crews, ensuring safety and quality in execution. Candidates should have 5-7 years of experience in construction, exposure to concrete formwork, and proficiency with relevant... 

    The Boldt Company

    Waukesha, WI
    11 hours ago
  • Milwaukee Succeeds in New Berlin, WI is seeking a Junior P&C Generalist to provide day-to-day HR support, oversee employee records, and assist with recruitment. The ideal candidate holds a Bachelor’s degree and has 2-4 years of experience, with strong critical thinking... 

    Milwaukee Succeeds

    New Berlin, WI
    4 days ago
  •  ...Insurance Sales Executive Sales Executive Unlock Your Potential at R&R Insurance Services Whether you're experienced in Commercial Insurance, Employee Benefits, or Personal Linesor ready to break into the industry with the right tools and mentorshipthis is your chance... 
    Local area

    Wausau Insurance

    Waukesha, WI
    1 day ago
  •  ...USA On-site Full-Time Requisition #: INSUR001632 Description Sales Executive - Unlock Your Potential at R&R Insurance Services Whether you’re experienced in Commercial Insurance, Employee Benefits, or Personal Lines—or ready to break into the industry with the right... 
    Base plus commission
    Full time
    Work at office

    R&R-Insurance-Services,-In

    Pewaukee, WI
    3 days ago
  •  ...SunMaid, Cinnabon. CBC believes that valuing employees ensures the success of the company. We...  ...we do. Position Overview Extra Route Sales Representative in the Waukesha, WI area....  ...regulations and be able to pass a DOT physical. Benefits Dental Insurance Health Insurance Paid... 
    Full time
    Contract work
    Shift work
    Weekend work

    Chicago Baking Co

    Waukesha, WI
    5 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Employee Benefits Sales Executive. Be the first to apply!