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

Entry Level Sales Executive - Employee Benefits

Cottingham & Butler

Entry Level Sales Executive - Employee Benefits

Madison, Wisconsin, United States

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 moreresources 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.

Cottingham & Butler
Vacancy posted 1 day ago
Similar jobs that could be interesting for youBased on the Entry Level Sales Executive - Employee Benefits in Madison, WI vacancy
  •  ...& Butler is actively looking for ambitious and driven entry-level Sales Executives in our Madison, Wisconsin location! Seeking all sales minded...  ..., not just insurance shoppers.In addition to designing employee benefits packages, we help with strategic planning, analytics,... 
    Entry level

    Cottingham & Butler

    Madison, WI
    1 day ago
  •  ...Job Description Job Description 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... 
    Suggested

    Cottingham & Butler

    Madison, WI
    a month ago
  •  ...About the Role: We are seeking motivated individuals to join our growing remote team as an Employee Benefits Specialist. This is an entry-level opportunity designed for candidates who are eager to learn the fundamentals of protecting employees, work directly with members... 
    Entry level
    Remote job
    Full time

    Zuzick Organization of Globe Life

    Madison, WI
    3 days ago
  •  ...the role:The National Accounts - Account Executive is responsible for maintaining...  ...Disability, AD&D, Dental and Voluntary Benefits• Support new business opportunities with...  ...voluntary benefits, dental and vision.• High level of technical knowledge in all components... 
    Suggested
    Full time
    Temporary work
    Work at office
    Local area
    Remote work

    Brown & Brown Insurance Services

    Madison, WI
    4 days ago
  • Employee Benefit Program - Technical Writer Anywhere Type: Contract Category: Technical/Proposal Writer Industry: Financial Services Workplace Type: Remote Standard Hours: Open Reference ID: JN -062026-107623 Date Posted: 09/23/2026 Shortcut: Description Remote... 
    Suggested
    Hourly pay
    Contract work
    Local area
    Remote work

    Eliassen Group

    Madison, WI
    3 days ago
  •  ...indomitable will to win. Job Summary The Sr. Employee Benefits Account Executive is responsible for retaining and...  ...advisor, and facilitating the sales cycle of identified opportunities to...  ...carrier fees. Responsibilities Senior level contact responsible for clients’ employee... 
    Immediate start
    Flexible hours

    Acrisure LLC

    Madison, WI
    3 days ago
  • $250k

     ...Employee Benefits Sales Leader Job Summary Seeking a dynamic and experienced Employee Benefits (EB) Sales Leader to join a team. This is a unique opportunity for a proven professional with a strong background in employee benefits sales and leadership to make a significant... 
    Local area

    Jobleads-US

    Madison, WI
    7 hours ago
  •  ...Job Description Job Description Regional Sales Leader, Employee Benefits Location: Madison, WI Cottingham & Butler is seeking an Employee...  ...business through hiring, managing, and developing sales executives. Attend sales calls to assist in closing deals and build... 
    Work at office

    Cottingham & Butler

    Madison, WI
    a month ago
  •  ...seeking an experienced and passionate employee benefits professional to drive successful outcomes...  .... Assist clients by developing and executing tailored benefit program strategies to...  ...funding strategies. Collaborate with the sales team to recommend products to enhance benefit... 
    Full time

    Cottingham & Butler

    Madison, WI
    7 days ago
  •  ...motivated individuals to join our growing remote team as a Benefits Enrollment Advisor. This is an entry-level opportunity designed for candidates who are eager to learn the fundamentals of protecting employees, work directly with members, and support the delivery of benefit... 
    Entry level
    Remote job
    Full time

    Zuzick Organization of Globe Life

    Madison, WI
    3 days ago
  •  ...trusted brand with high customer retention * Be part of a supportive sales team that offers consistent 1:1 coaching, ongoing sales...  ...teams to ensure seamless customer onboarding Compensation & Benefits * Competitive base salary + monthly uncapped commissions and... 
    Entry level

    UniFirst

    Madison, WI
    6 hours ago
  • $57k - $62k

     ...Description Job Description We are seeking a motivated Entry-Level Sales Representative to join our growing team in Madison, WI....  ...organizational and time management skills. Additional Information Benefits Competitive annual salary: $57,000 - $62,000 .... 
    Entry level
    Full time

    Alphabe Insight Inc

    Madison, WI
    2 days ago
  • $60k

    Sales Consultant Metro Kia of Madison | Madison, WI Metro Kia...  ...Compensation & Benefits * Competitive commission-...  ...* Paid time off * Employee discounts on vehicles and service...  ...,000+ annually for motivated entry-level consultants * $100,000+... 
    Entry level
    Weekend work
    Afternoon shift

    Metro Kia of Madison

    Madison, WI
    3 days ago
  •  ...No prior industry experience required Meet with clients on Zoom to help them enroll in benefit programs Explain options in a clear, simple, and relatable way Help clients complete online enrollment forms accurately Schedule and manage virtual appointments... 
    Entry level
    Full time

    Zuzick Organization of Globe Life

    Madison, WI
    2 days ago
  •  ...to join our growing remote team as a Entry Level Remote Benefits Advisor. This is an entry-level opportunity...  ...learn the fundamentals of protecting employees, work directly with members, and...  ...This is a remote, client-facing sales role where you will meet with clients... 
    Entry level
    Remote job
    Full time

    Zuzick Organization of Globe Life

    Madison, WI
    1 day ago
  •  ...Description Vector Marketing is interviewing immediately for entry level sales positions. Primary responsibilities include selling our Cutco...  .... With a busy holiday season ahead, our sales reps benefit from a position that pays weekly and allows them to work around... 
    Entry level
    Weekly pay
    Full time
    Temporary work
    Part time
    Work experience placement
    Internship
    Seasonal work
    Work at office
    Immediate start
    Work from home
    Flexible hours

    Vector Marketing

    Madison, WI
    2 days ago
  • $200k - $300k

     ...Windows & Baths, a Renuity Company In-Home Sales Representative Average reps can...  ...! ~ W2 employment - comprehensive benefits packages, PTO, 401(k) with match ~ State...  ...current marketing leaders started in entry-level roles. As part of our team and the... 
    Entry level
    Local area

    Renuity

    Madison, WI
    16 hours ago
  • $60k - $80k

     ...Overview GovCIO is currently hiring for an entry-level proposal writer to join our dynamic team...  ...provided in your application Employee Perks At GovCIO, we consistently hear that...  ...employees have access to a range of perks and benefits to support their personal and... 
    Entry level
    Full time
    Currently hiring
    Remote work
    Flexible hours

    GovCIO

    Madison, WI
    2 days ago
  •  ...Pharmaceutical Sales Representative (Primary - Specialty and Entry Level) Pharmaceutical Sales Rep - Job Description   We are a healthcare industry specialty...  ...healthcare professional and physician customers benefit from a diverse group of products and services.... 
    Entry level
    Full time
    Work at office

    Prism Biotech

    Madison, WI
    14 days ago
  •  ...Spectrum Residential Connectivity Outside Sales Representative Goal-oriented. Self-...  ...building relationships and sharing the benefits of our bundled services, working every lead...  .... Position details: Full-time Entry-level Travel in assigned territory... 
    Entry level
    Full time

    Spectrum

    Madison, WI
    4 days ago
  • $40k - $45k

     ...administrative tasks including data entry, assisting in the planning and execution of company-wide events, and...  ...is an in-person, full-time, entry level position. Travel required. Looking...  ...Must be able to lift 25+ pounds Benefits Health Insurance Dental Insurance... 
    Entry level
    Full time
    Flexible hours

    Everlight Solar

    Madison, WI
    1 day ago
  •  ...Entry Level Sales Executive - Trucking Madison, Wisconsin, United States This position requires a 1012-week training session in Dubuque,...  ...clients and provide the amazing career opportunities our employees want and deserve. This is why we are a growth company and... 
    Entry level
    For contractors

    Cottingham & Butler

    Madison, WI
    4 days ago
  •  ...Meet with clients virtually to understand their needs Advise clients on union-backed benefits and available options Guide clients through solutions that best fit their situation Build trust and maintain strong client relationships Stay organized with follow-... 
    Entry level
    Remote job
    Full time

    Zuzick Organization of Globe Life

    Madison, WI
    16 hours ago
  • $300k

     ...Sales Representative Company: US0018 Sysco Baraboo, LLC Sales...  ...Team and explore all the benefits and perks. Why you should...  ...pathing opportunities for both entry level, and experienced individuals...  ...benefits package including an Employee Stock Purchase Plan, & 401(k)... 
    Entry level
    Internship
    Relocation
    Weekend work
    Afternoon shift

    Sysco

    Madison, WI
    3 days ago
  • $17 - $18 per hour

     ...pulling, packing, stocking, receiving, and inventory. First shift employees will also have opportunities to cross-train as workload allows....  ...opportunity. Pay Details: $17.00 to $18.00 per hour Benefit offerings available for our associates include medical, dental,... 
    Entry level
    Hourly pay
    Permanent employment
    Temporary work
    Local area
    Monday to Friday
    Shift work
    Day shift
    Afternoon shift

    Adecco

    Middleton, WI
    6 days ago
  • $300k

     ...Sales Representative Are you an experienced sales professional...  ...team and explore all the benefits and perks. Why you should...  ...pathing opportunities for both entry level, and experienced individuals...  ...benefits package including an Employee Stock Purchase Plan, & 401(k)... 
    Entry level
    Internship
    Relocation
    Weekend work
    Afternoon shift

    Sysco

    Madison, WI
    4 days ago
  •  ...trusted brand with high customer retention Be part of a supportive sales team that offers consistent 1:1 coaching, ongoing sales...  ...teams to ensure seamless customer onboarding Compensation & Benefits Competitive base salary + monthly uncapped commissions and quarterly... 
    Entry level

    UniFirst

    Madison, WI
    1 day ago
  • $17.39 - $27.17 per hour

     ...billion in tire and auto service sales, Bridgestone Retail...  ...for full-time and part-time employees, and a 401k plan to help build...  ...and/or services, performing entry-level vehicle services, and ensuring...  ...a plus. Our Crew Knows Benefits ~ Medical, Dental and Vision... 
    Entry level
    Daily paid
    Minimum wage
    Full time
    Temporary work
    Part time
    Local area
    Flexible hours

    Bridgestone Americas

    Madison, WI
    4 days ago
  • $20 per hour

     ...Entry Level Sales Representative $20/Hour + Uncapped Bonuses! Get started next week! No Experience Needed – Career Growth Opportunities – Uncapped Earnings As an Entry Level Sales Rep, you’ll meet with homeowners in local neighborhoods, start conversations... 
    Entry level
    Local area
    Monday to Friday

    Renuity

    Madison, WI
    1 day ago
  • $19 per hour

     ...+ hours outside every day No experience required – we provide paid training Ability to work a 1:00PM - 9:00PM schedule Benefits and Pay: ~$19/hr base pay. ~$100 potential weekly bonuses for FT staff. ~ Paid Time Off provided. ~ Subsidized healthcare... 
    Entry level

    Donor Development Strategies

    Madison, WI
    3 days ago

Do you want to receive more vacancies?

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