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Madison employee benefits sales

27 employee benefits sales jobs found in Madison

Cottingham & Butler
08/15/2025  
Entry Level Sales Executive - Employee Benefits
Cottingham & Butler is actively looking for ambitious and driven entry-level Sales Executives in our Madison, Wisconsin location! Seeking all sales minded, soon-to-be college graduates, recent college graduates, or individuals with 1-3 years of sales experience who are motivated by financial rewards. What You'll Get: At Cottingham & Butler, we offer an exceptional sales career that opens the door to boundless opportunities and unlimited earning potential. You will be immersed in a dynamic environment surrounded by a team that is dedicated to equipping you for success. Through comprehensive training, unparalleled service support, unique resources, and the necessary tools, we ensure that you have everything you need to build a highly lucrative sales career. What You'll Do: Learn the business and become a trusted advisor to company leaders. Identify, qualify, and close prospects. Manage and retain your book of business and actively work towards its growth...
Cottingham & Butler Madison, WI
Cottingham & Butler
01/20/2025  
Experienced Sales Executive - Employee Benefits
We are seeking an experienced Employee Benefits Insurance Broker with at least 3 years' experience of B2B sales in the employee benefits space. This role will be responsible for providing expert advice and guidance to clients in navigating the complex landscape of employee benefits insurance and programs. Individuals who apply should possess: Proven experience and success as an insurance broker, with a focus on employee benefits A strong understanding of employee benefits products Detail-oriented with strong analytical skills, capable of evaluating complex insurance plans and identifying cost-saving opportunities.  Excellent communication and interpersonal skills, with the ability to build rapport and trust with clients. Join a Winning Team: The individual in this role will joining a team with a solid track record of success in the employee benefits insurance industry. Over the years, our team has experienced significant growth of 18% (driven organically) and a...
Cottingham & Butler Madison, WI
NGL - National Guardian Life Insurance Company
06/26/2026  
Agent Solutions Coordinator (Hybrid - In Office 10 days/Month)
We are adding an Agent Solutions Coordinator !  This is a hybrid position requiring individuals to work in office 10 days per month; or as needed for business needs.   Who We Are: Since 1909, National Guardian Life Insurance Company (NGL) has been one of America’s most successful and highly rated independent life insurance companies. We specialize in a suite of innovative products for life’s journey, giving people the financial stability, careful guidance and peace of mind to lead a life filled with confidence, dignity and grace.   NGL's Core Values – integrity, dependability, collaboration, compassion and growth are a foundation of our company and help to build on the interactions we have with our policyholders, partners, funeral homes and each other. We believe in creating an inclusive, welcoming environment for all where diversity is celebrated, and everyone is encouraged to live their best, most authentic self. We offer  Employee Resource Groups for...
NGL - National Guardian Life Insurance Company Madison, WI Full Time
TruStage
06/25/2026  
Consultant I, Compliance (Hybrid)
At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Purpose:   This position is responsible for delivering high quality compliance services to clients. Services include research, analysis and training/education on compliance issues in order to meet our business objectives. This role is also responsible for collaborating, educating and advising our business partners on risk identification and mitigation strategies....
TruStage Madison, WI Full Time
M3 Insurance
06/24/2026  
Property and Casualty Client Manager
The Opportunity Are you ready to embark on a fulfilling career journey as a Property & Casualty Client Manager? If you’re passionate about providing exceptional client service, building strong client relationships, and have a knack for problem-solving, this is the opportunity for you. In this role, you'll be at the forefront of supporting our sales efforts, ensuring client satisfaction, and navigating the ever-evolving landscape of commercial insurance. This role isn't just about managing accounts—it's about forging lasting connections, providing unparalleled service, and contributing to the success of our clients and our team. You’ll gain valuable experience in insurance while working in a collaborative and supportive environment where your skills and expertise are valued.   How You Will Make an Impact Take the lead on managing assigned books of business, guiding internal resources, and delegating tasks effectively under the direction of experienced...
M3 Insurance Madison, WI Full Time
TruStage
06/24/2026  
IT Software Engineering Manager
At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Responsibilities: Team Leadership & Management Lead and mentor multiple development teams, fostering a culture of collaboration, innovation, and continuous improvement. Develop and improve team capabilities through mentoring, training, and performance management. Work closely with senior leadership to develop and execute the application development strategy, aligning...
TruStage Madison, WI Full Time
Sentry
06/16/2026  
Human Resources Specialist
Sentry’s HR Specialists serve as the key HR representative in the field office in which they are located. This role will be located at our Middleton, WI office location in a hybrid work model. The HR Specialist provides support and guidance to Sentry managers and associates across a range of areas such as associate relations and talent acquisition. What You'll Do As an HR Specialist, you will: Coach and guide managers in assessing need for and developing associate-related communications, including corrective action documentation. Engage and meet with business unit leaders and associates developing relationships, trust and engagement.  Serve as an on-site conduit for multiple HR and Corporate departments.  Coordinate the termination process and serve as a point of contact for terminated associates. Coordinate the employee exit process, conduct exit interviews, and provide critical information and input into termination decisions.  Review initial complaints,...
Sentry Madison, WI Full Time
TruStage
06/14/2026  
Creative Execution Lead (Hybrid: Madison, WI)
At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Purpose: This position reports to the Director, Creative Services and this role is responsible for executing and overseeing tier 2 creative projects for the creative services team.  This role involves managing the production and delivery of creative assets, ensuring they meet brand guidelines and project objectives. This position collaborates closely with the senior creative...
TruStage Madison, WI Full Time
TruStage
06/10/2026  
Sr. Manager, Brand Strategy & Enterprise Marketing (Hybrid: Madison, WI/Waverly, IA)
At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Purpose:     This position supports the strategic development and activation of the TruStage brand and plays a key role in strengthening brand presence, consistency, and experience across the enterprise. Reporting to the Head of Brand Strategy & Engagement, this role translates enterprise brand strategy into clear guidance, programs, and brand marketing initiatives...
TruStage Madison, WI Full Time
Sentry
06/01/2026  
Business Product Analyst-Personal Lines
In this role, you will work hand in hand with Business partners to document and file our products with state DOIs, as well as to help build systematic underwriting rules. As one of the largest mutual insurance companies in the US, Sentry is committed to offering coverage at a competitive price and providing outstanding service and support. To offer our customers competitive products and outstanding service it takes an effective team. A Personal Lines Product Analyst is a key part of the team in our Madison, WI office. This is a great opportunity to start or grow your career, while taking on new challenges to develop professionally. Bring your strong curiosity, multi-tasking skills and a “can do” attitude to this opportunity. This position can be filled as a Product Analyst or Associate Product Analyst based on the selected candidate’s related skills and experience. This position will be located at our office in Madison, WI in a hybrid work model and is not a fully remote...
Sentry Madison, WI Full Time
AAA - Auto Club Group (ACG)
06/01/2026  
Insurance Sales Agent - Madison
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:   Insurance Sales Agent AAA – The Auto Club Group | Madison, WI Full ‑ time | W ‑ 2 | Base Pay + Incentives + Full Benefits $5,000 Signing Bonus for new hires **To qualify for the Sign-On Bonus, applicants must be new to ACG (not applied in the last 180 days.) There is a 1-year payback clause if your employment is terminated prior to completing 12 months of employment.  Additional details can be provided by our Recruiting Team at the time of application** 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...
AAA - Auto Club Group (ACG) Madison, WI Full Time
TruStage
05/29/2026  
Compensation Consultant (Hybrid - Madison, WI or Waverly, IA)
At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Purpose: This position provides senior/advanced level compensation consulting, design, development, and administration to multiple, highly complex, diverse client areas under minimal direction. This position collaborates and consults with HR partners and business leaders to develop effective solutions in the following areas: job design, analysis and evaluation, sales incentive...
TruStage Madison, WI Full Time
TruStage
05/28/2026  
Associate Regional Sales Consultant - Retirement Plans
At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Purpose:   This position will partner with the retirement wholesaling team, along with product, and implementation teams to provide support for pre- and post-sale activities. This position will work closely with external and internal wholesalers to enhance distribution through financial advisors, TPA’s, DCIO’s and other centers of influence. This position will collaborate with...
TruStage Madison, WI Full Time
M3 Insurance
05/27/2026  
Retirement Plan Manager II
  The Opportunity Are you passionate about building strong client relationships and delivering exceptional service in the retirement plan industry? M3 is seeking a skilled Retirement Plan Manager II to support our M3 Financial team in servicing employer-sponsored retirement plans, including 401(k), 403(b), and 457(b) plans. As a Retirement Plan Manager II, you will utilize your retirement plan knowledge and professional communication skills to serve as a primary point of contact for clients, maintain and grow relationships, and ensure high levels of client satisfaction. You will work closely with Retirement Plan Consultants, the Managing Director, and other M3 Financial staff — including conducting educational meetings independently and participating in group sales presentations.   How You Will Make an Impact Serve as the primary point of contact for all service inquiries for new and existing clients, providing excellent customer service both in-house...
M3 Insurance Madison, WI Full Time
AAA - Auto Club Group (ACG)
05/24/2026  
Insurance Sales Agent - Madison, WI
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:   $5,000 Signing Bonus for new hires **To qualify for the Sign-On Bonus, applicants must be new to ACG (not applied in the last 180 days.) There is a 1-year payback clause if your employment is terminated prior to completing 12 months of employment.  Additional details can be provided by our Recruiting Team at the time of application** 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...
AAA - Auto Club Group (ACG) Madison, WI Full Time
TruStage
05/20/2026  
Associate Account Representative (Sales Development Program) - Hybrid Madison
At TruStage, we’re on a mission to make a brighter financial future accessible to everyone.  We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Purpose:   This position is the first-level, limited term position (18-24 months) as part of our broader Sales Development Program designed to train and prepare individuals for broader sales roles. This position supports sales efforts through coordination, customer care, and learning sales processes under the guidance of a Sales Manager. The individual develops core...
TruStage Madison, WI Full Time
Cottingham & Butler
05/13/2026  
Employee Benefits Client Consultant
A year from now, you will look back on this single job application and reflect on your experience. The personal growth, the knowledge you’ve gained, and the professional evolution you’ve achieved will be nothing short of remarkable. This transformation is credited to your dedication and the guidance of our skilled leaders, who are eager to mentor you in the intricate world of employee benefits. At Cottingham & Butler, we invest in people that want to be great. Our Client Consultant Development Program is more than a training course—it’s a gateway to success in our benefits division. Our program is designed to mold you into a well-informed, proficient Benefits Manager, equipped to deliver top-tier analysis, strategic recommendations, and dedicated service to our clients and prospects, enhancing their employee benefit programs. Here’s how we empower you to make an impact: Develop Benefit Plan Recommendations : Dive deep into client data to craft custom benefit...
Cottingham & Butler Madison, WI
Cottingham & Butler
05/13/2026  
Senior Employee Benefits Client Consultant
We are seeking an experienced and passionate employee benefits professional to drive successful outcomes for clients and their programs. As an Employee Benefits Client Consultant, you’ll play a critical role in building strong client relationships, providing high-quality analysis, and delivering strategic recommendations that ensure positive outcomes for our clients. With your expertise, you’ll serve as a trusted advisor to clients across various industries, sizes, and geographies. Essential Functions: • Build Client Relationships: Establish yourself as the primary advisor for benefits-related issues. Assist clients by developing and executing tailored benefit program strategies to retain and attract employees. Support HR leaders in navigating legal compliance requirements (e.g., HIPAA, FMLA, COBRA) and other functions. • Team Collaboration: Work within a cross-functional team to address client needs in analytics, compliance, communications, technology, marketing, and...
Cottingham & Butler Madison, WI
AAA - Auto Club Group (ACG)
05/03/2026  
Insurance Sales Agent - Madison
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:   Insurance Sales Agent AAA – The Auto Club Group | Madison, WI Full ‑ time | W ‑ 2 | Base Pay + Incentives + Full Benefits $5,000 Signing Bonus for new hires **To qualify for the Sign-On Bonus, applicants must be new to ACG (not applied in the last 180 days.) There is a 1-year payback clause if your employment is terminated prior to completing 12 months of employment.  Additional details can be provided by our Recruiting Team at the time of application** 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...
AAA - Auto Club Group (ACG) Madison, WI Full Time
Allstate
04/11/2026  
Licensed Insurance Sales Representative (Remote / Home-Based)
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.  Job Description Allstate’s sales organization is growing its virtual workforce, and we are looking for highly motivated individuals that thrive in a fast-paced sales environment and enjoy being rewarded for their efforts. At Allstate, we are committed to offering a reputable product suite that protects people from life’s uncertainties so they can realize their hopes and dreams. As a full-time Insurance Sales Representative, you will: Engage with active insurance shoppers via inbound/outbound calls, live chat, SMS, and more in a work from home call...
Allstate Madison, WI Full Time

 

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