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. What You’ll Do 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...

Are you an experienced insurance professional ready to elevate your career in an environment that values growth, innovation, and work-life balance? R&R Insurance Services, one of Wisconsin’s largest independent agencies, is looking for an Experienced Commercial Lines Account Manager to join our award-winning team. If you’re looking for a place that provides both professional development and a supportive, dynamic workplace, R&R could be the next great chapter in your career. At R&R, we don’t just fill positions—we build careers. We provide the tools, the mentorship, and the opportunities for you to take your skills to the next level. If you're ready for a workplace that feels like a community and a team that values your contributions, we want to hear from you. What You’ll Do As a Commercial Lines Account Manager, you will leverage your experience and work directly with clients to provide top-tier service while supporting the Commercial Lines department. In this...

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...

Responsibilities The Vice President of Commercial Lines Service is responsible for the overall leadership, strategy, and performance of R&R’s Commercial Lines Service organization. This role partners closely with Commercial Sales leadership and executive leadership to ensure a scalable, efficient, and client-focused service model. Key responsibilities include: Provide strategic leadership and direction for the Commercial Lines Service Team, supporting continued growth and operational excellence Lead, mentor, and develop service leadership and team members, with a strong focus on talent development, engagement, and retention Evaluate and refine business processes to improve efficiency, consistency, and client experience Drive initiatives related to workflow optimization, technology adoption, and service delivery improvements Partner with Commercial Sales leadership to support new business growth while maintaining high service standards Oversee hiring,...

Client Executive – Relationship Builder. Problem Solver. Insurance Superhero. We're looking for a Client Executive who loves helping clients, and can anticipate needs before anyone even says them out loud. If you enjoy being the go-to expert, keeping things running smoothly, and partnering with Sales Executives to make sales happen—this role may be for you. Drive the Client Experience Review policies and contracts with a sharp eye. Dig into loss data, spot trends, and help clients stay ahead. Oversee claims, project experience mods, and  conduct quarterly claims reviews. Be the Sales Executive's Secret Weapon  Prep proposals, renewals, and client materials that look sharp and tell the right story. Identify opportunities to round out accounts and add value. Join meetings with prospects and clients—helping plan, strategize, and follow through. Keep workflows on track and make sure nothing slips through the cracks....

We know that finding the right role is a two-way street — sometimes, the right opportunity just hasn’t been posted yet. If you’re passionate about what you do, curious about a career with one of Wisconsin’s largest independent insurance agencies, and think R&R could be the place for you, we encourage you to apply here. This general application is for individuals who don’t see a specific opening that fits their experience right now, but want to be considered for future opportunities across any of our teams — including: Client Services (Personal, Commercial, Employee Benefits, or Wealth Management) Sales & Business Development Marketing & Communications HR & Talent Acquisition Finance & Accounting Administrative Support Claims, Risk Management & Safety Technology & Systems Support Whether you’re experienced in the insurance industry or just starting your career journey, we believe the right fit starts with the right people....

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 tools and mentorship—this is your chance to build a successful career with one of the largest and most respected independent insurance agencies in the Midwest. What You’ll Do: Build and cultivate meaningful relationships with new prospects and referral sources, fostering long-term trust and credibility. Drive business growth by prospecting, networking, and generating leads in your target market. Deliver tailored, consultative insurance solutions that align with client needs and long-term goals. Manage and expand your book of business with a focus on building sustainable, trust-based client relationships. Develop and present customized insurance and risk management strategies for clients, collaborating with internal teams to ensure exceptional service...

What You’ll Do As an Account Manager II, you’ll manage day-to-day service responsibilities for employee benefits clients while acting as a knowledgeable, dependable partner throughout the client service cycle. Client Relationship & Service Management Independently manage a book of fully insured and level-funded employee benefits clients (generally 2–100 enrolled employees) Serve as the primary day-to-day contact for assigned accounts, ensuring strong relationships and client satisfaction Lead renewals, annual reviews, and ongoing plan support, including claims, billing, enrollment, and service issues Present renewal data, plan comparisons, and market analysis to clients in partnership with the consultant Manage implementations and carrier changes from start to finish Collaboration & Team Support Attend client meetings (including in-person meetings) alongside consultants as needed Mentor and support Account Manager I team members Work...