Entry Level Sales Executive - Employee Benefits

Posted 7/29/2026 · last confirmed live 8/26/2026

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 to unlock substantial financial growth. Strategize and develop customized solutions for clients, leveraging available programs to deliver services that exceed client expectations. Cultivate strong relationships with top decision makers, ensuring long-term client retention. Collaborate with our service team to create compelling proposals and deliver impactful presentations to clients and prospects. Earn relevant designations and stay up-to-date on continuing education credits provided by the company to enhance your professional growth and earning potential.   There are 30,000 insurance brokers in the US that claim to offer great sales careers, but in reality, very few sales executives ever achieve a $1 million book of business. We put our money where our mouth is – almost ALL of our sales executives have a million-dollar book by their 10th anniversary.   How do our producers achieve such consistent results?  We make it easy by surrounding them with everything they need to be successful, including: Experienced Account Management Teams  – Your clients will be in good hands with our account management teams. They are capable and proficient. In addition to having skilled account managers, we intentionally build redundancy into the teams to ensure that clients get the best service possible. In-House Specialists - Our team includes people that specialize in compliance, HR consulting, analytics, client communications, worksite products, stop loss and technology.  Tools & Resources - You will have assessments, checklists, audits, etc. that you can use to tailor custom strategies for each client. You will also have access to partner companies that will provide you with additional resources, such as ThinkHR and Zywave, etc. We are consultants, not just insurance shoppers. In addition to designing employee benefits packages, we help with strategic planning, analytics, cost containment, regulatory and compliance issues, and M&A/ due diligence, etc.   People We Hire: If you thrive in a fast-paced, competitive environment and possess a relentless drive for success, Cottingham & Butler is the ideal place for you. You will be surrounded by industry-leading professionals, including several teammates who manage books of business exceeding $1 million. Additionally, you'll have access to our exceptional service teams and in-house specialists focused on account management, technology, compliance, analytics, client communications, and more—resources that will elevate your sales performance and financial success.   About Cottingham & Butler: At Cottingham & Butler, we sell a promise to help our clients through life’s toughest moments. To deliver on that promise, we aim to hire, train, and grow the best professionals in the industry. We look for people with an insatiable desire to succeed, are committed to growing, and thrive on challenges. Our culture is guided by the theme of “better every day” constantly pushing ourselves to be better than yesterday – that’s who we are and what we believe in. As an organization, we are tremendously optimistic about the future and have incredibly high expectations for our people and our performance. Our ability to grow as a company, fuels investments in new resources to better serve our clients and provide the amazing career opportunities our employees want and deserve. This is why we are a growth company and why we are committed to being better every day.  Want to learn more? Follow us on  www.CottinghamButler.com  |  LinkedIn  |  Facebook

This role is published by Cottingham & Butler on greenhouse. SwiftFit is not the employer and does not accept applications.