10 inside sales jobs found in Waukesha, WI

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...

It’s a great time to join AAA The Auto Club Group!   JOIN THE TEAM COMMITTED TO DRIVING YOUR CAREER FORWARD Job Type: Full time   Exempt/Non Exempt:   Hourly Job Description:   Job Description Insurance Sales Agent AAA – The Auto Club Group | Madison, WI Full ‑ time | W ‑ 2 | Base Pay + Incentives + Full Benefits $2,500 Signing Bonus for new hires AAA – The Auto Club Group | Madison, WI Full‑time | W‑2 | Base Pay + Incentives + Full Benefits Looking to build a stable sales career with real benefits? Join America’s most trusted brand with over 100 years of service as an Insurance Sales Agent- no insurance background required   If you enjoy helping people, building relationships, and earning more through performance, we’ll provide the training, tools, and support to help you succeed Why This Role Works for Many Candidates Reliable base pay plus performance incentives —earn more as you grow Full benefits...

Marketing & Communications Specialist  Are you a creative marketing professional with a background in commercial insurance who enjoys combining strategy, communication, content creation, and business development support in meaningful work? R&R Insurance Services is seeking a Marketing & Communications Specialist to support our Commercial Lines practice in Waukesha. This role blends campaign strategy, digital communications, content development, branding, and sales support, while helping strengthen the R&R brand across the agency. If you thrive in a collaborative environment and enjoy turning ideas into effective marketing, communication, and business development initiatives, we’d love to connect. What You'll Do As a key member of the team, you’ll support marketing initiatives that strengthen client relationships, drive business development, and elevate the R&R brand. Responsibilities include: Coordinate marketing campaigns and communications,...

Workers' Compensation Practice Leader Are you a workers’ compensation leader who thrives on helping organizations reduce risk, improve outcomes, and build smarter long-term strategies? R&R Insurance Services, one of the Midwest's largest independently owned insurance agencies, is seeking a Workers’ Compensation Practice Leader to shape strategy, drive growth, and elevate outcomes across our practice. This role is ideal for a workers' compensation professional who combines deep technical expertise with a consultative approach to risk management, client strategy, analytics, and business development. You'll help shape a growing specialty practice, influence client outcomes, and expand R&R's expertise across complex workers' compensation programs. What You'll Do Practice Leadership Lead the strategic direction and continued growth of R&R’s practice. Develop tools, resources, and best practices that strengthen consistency and service delivery across the...

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....

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...

Responsibilities Summary: When someone needs coverage for the unique, the unusual, or the unconventional, they come to Burns & Wilcox. Burns & Wilcox offers unparalleled resources and exposure for those looking to grow their career in the specialty insurance industry. We are looking for candidates with an entrepreneurial spirit, drive for career advancement and desire to develop relationships to join our team as a Senior Associate Underwriter.  Our Senior Associates underwrite and supervise a portion of an Underwriter’s book of business, support renewal and new business development, and have the opportunity to achieve full underwriting authority.     Underwrite and supervise a portion of an Underwriter’s book of business, focused on renewals and new business Evaluate, classify, and rate each risk to determine acceptability, coverage, and pricing to prepare quotes Assist Underwriters to develop and execute...

About HUB In a rapidly changing world, HUB advises businesses and individuals on how to prepare for the unexpected. As one of the world’s largest insurance brokers, our focus is dedicated to providing our customers with the peace of mind that what matters most will be protected — through unrelenting advocacy and tailored insurance solutions that put our clients in control. Our growing team of professionals across North America represents a broad, deep and one-of-a kind aggregation of entrepreneurs and leaders recognized for their excellence throughout the insurance community. Why Choose HUB? Throughout our network of more than 450 HUB offices in North America, we offer a competitive, exciting and friendly work environment that strategically positions our employees for longevity and success. At HUB, we believe in investing in the future of our employees, and provide continuous opportunities for growth and development.  Our entrepreneurial culture fosters an environment...

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 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...