Experienced Sales Executive - Employee Benefits
Cottingham & Butler
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 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 client retention over 90%. This growth is a testament to our team's ability to adapt to changing market dynamics, anticipate client needs, and deliver results.
Unmatched Sales Support: We surround our sales team 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.
Ultimately, we like to win and have a track record of doing it year-over-year. Many of the best brokers in the nation have chosen to call Cottingham & Butler home and have built careers unlike anything in the industry. Here is a link to a highlight video from one of our National Sales Celebration Event.
Pay & Benefits
- Full salary + bonus
- Most Benefits start Day 1
- Medical, Dental, Vision Insurance
- Flex Spending or HSA
- 401(k) with company match
- Profit-Sharing/ Defined Contribution (1-year waiting period)
- PTO/ Paid Holidays
- Company-paid ST and LT Disability
- Maternity Leave/ Parental Leave
- Subsidized Parking
- Company-paid Term Life/ Accidental Death Insurance
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 | LinkedIn | Facebook
- ...for ambitious and driven entry-level Sales Executives in our Madison, Wisconsin location! Seeking... ...need to be successful, including: Experienced Account Management Teams – Your... ...insurance shoppers.In addition to designing employee benefits packages, we help with strategic...Suggested
- ...motivated individuals to join our growing remote team as an Employee Benefits Specialist. This is an entry-level opportunity designed for... ...developing client-focused strategies under the direction of experienced team leaders Maintain consistent communication with members...SuggestedRemote jobFull time
- ...Experienced Sales Executive - TransportationMadison, Wisconsin, United StatesCottingham & Butler Transportation... ...& BenefitsFull salary + bonusMost Benefits start Day 1Medical, Dental, Vision... ...the amazing career opportunities our employees want and deserve. This is why we are...SuggestedFor contractors
- ...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 Our client...SuggestedHourly payContract workLocal areaRemote work
- ...Job Description We are seeking an experienced and passionate employee benefits professional to drive successful... ...Assist clients by developing and executing tailored benefit program strategies... ...strategies. Collaborate with the sales team to recommend products to enhance...SuggestedFull time
- ...meaningful to teammates.About the role:The National Accounts - Account Executive is responsible for maintaining persistency on an assigned book... ...include Group Life, Disability, AD&D, Dental and Voluntary Benefits• Support new business opportunities with existing clients •...Full timeTemporary workWork at officeLocal areaRemote work
- ...Employee Benefits Account Executive Acrisure is a global Fintech leader that combines the best of humans and high tech to offer multiple financial... ...knowledge of employee benefits solutions, and assisting with the sales and renewal process to help achieve client objectives....Immediate startFlexible hours
- ...the world. Most of our employees are in the United... ...looking for an Outside Sales Representative in the... ...sales performance and execute against sales goals.... ...collaborate with more experienced team members when appropriate... ...under local law. Benefits include medical, dental...Minimum wageTemporary workLive inLocal area
- ...results. We are currently adding experienced transportation producers. Joining our sales team will allow you access to... ...Celebration Events: Pay & Benefits ~ Full salary + bonus ~ Most... ...amazing career opportunities our employees want and deserve. This is why we...For contractors
- ...without being overly sales-focused, follow through... ...Position: Healthcare Sales Executive Location:... ...We're looking for an experienced Outreach Representative... ...ventilator or g-tube. BENEFITS: ~ Generous Paid... ...(PTO) for full time employees to ensure a healthy...Full timeLocal areaMonday to Friday
$125k
...get flexibility that’s real, benefits you can count on, and a team... ...opportunity As a Senior Sales Executive, you will drive net-new logo... ...This is an opportunity for an experienced hunter to build a meaningful... ...build a better employee experience, improve workforce...Local areaRemote work- ...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
- Burlington Stores, Inc. is hiring a Retail Sales Associate in Wisconsin. You will greet customers, assist with merchandise, and maintain... .... You’ll earn a base wage with associate discounts and access to benefits for eligible part-time staff. #J-18808-Ljbffr BurlingtonPart timeFlexible hoursNight shift
- ...levels of personnel. Highly adaptable to changing work environments Must be able to travel as required. Must prioritize and execute tasks and assignments. Must have excellent analytical and problem solving skills. The above statements are intended to...
$18 - $22 per hour
...Immediate Opening- Experienced Leasing Consultant-Heyday Sun Prairie Sun Prairie, WI 53590 Pay: $18-$22 hourly, plus Sales commissions. Growth Opportunity Founded in 19... ...industry. We offer an outstanding benefits package including... - 401K, with a...Hourly payFull timeWork at officeLocal areaImmediate startFlexible hoursAfternoon shift$120k - $160k
...This Sr. Federal Account Executive is responsible for generating sales of comprehensive energy... ...You will be armed with an experienced technical support... ...negotiations. Articulate the benefits of infrastructure... ...their fields, Honeywell employees are eligible for a comprehensive...Contract workTemporary workFlexible hours- ...This isn’t a revolving-door sales job; it’s a career opportunity... ...and processes directly from an experienced rep before taking full... ...pipelines Technical & Program Execution • Work directly with... ...preferred Compensation & Benefits We offer a competitive compensation...Remote work
- ...Field Sales Representative Remote, Nationwide Our client... ...company is positioned to give an experienced seller the resources and... ...responsibility over time. Health benefits and a 401(k) program with... ...Signal is an award-winning, executive search firm specializing in various...For contractorsImmediate startRemote work
$60k
Sales Consultant Metro Kia of Madison | Madison, WI Metro Kia... ...Compensation & Benefits * Competitive commission-... ...* Paid time off * Employee discounts on vehicles and service... ...* $100,000+ annually for experienced sales professionals(Uncapped...Weekend workAfternoon shift- ...provider to hire an Industrial Sales Representative to manage and... ...excellent opportunity for an experienced industrial sales professional... ...program, comprehensive benefits, and extensive technical training... ...technical resource. Develop and execute a territory growth strategy...
$72k
...About the Role: We are seeking a driven sales professional to drive new business... ...HNAS) delivers flexible, cost-effective employee health benefits solutions. As part of Highmark Health,... ...and health plan concepts to C-suite executives and key decision-makers. Education...For contractorsWork at officeLocal areaRemote workFlexible hours$125k
...Treeline, Inc., an award-winning sales recruiting and executive search agency, offering strategic sales... ...Company Profile Our client provides an Employee Empowerment platform to promote... ...hunting strategy to engage key HR, Benefits, and Total Rewards decision-makers....Remote work- ...identify a driven National Sales Representative ready to open... ...initially work alongside an experienced sales professional to learn the... ...your own market: Create and execute a national new-business-development... .... Compensation and Benefits Competitive base salary...Temporary workFlexible hours
$25k
...unparalleled service. We are seeking a Corporate Sales Executive to cover WI, IA, MN, and the Northen part of IL.... ...sales Strong analytical and problem-solving skills Benefits And Additional Compensation Eligible employees receive a comprehensive benefits package, which...Full timeRemote workNight shift- ...Entry Level Sales Executive - TruckingMadison, Wisconsin, United StatesThis position requires... ...that set us apart:Our Team. 300+ experienced professionals that specialize in the trucking... ...the amazing career opportunities our employees want and deserve. This is why we are a...For contractors
- ...Sales Executive – OEM & Channel Development (Medical Display Solutions) Why Join Beacon? Join a growing global medical technology company... .... Receive structured product and sales training from experienced global teams, with opportunities to grow based on your...Internship
- ...ages. As a Band and Orchestra Sales Specialist, you’ll build... ...Ongoing coaching and support from experienced music retail professionals... ...knowledge. Why Heid Music? Employee discount Flexible... ...Health/Vision/Dental and PTO benefits available for full-time team...Hourly payFull timeFlexible hoursAfternoon shift
- ...( is the advertising sales division of Spectrum.... ...Sales Team as an Account Executive to grow our sales,... ...outside or B2B sales experienceAbility to use data in the... ...SAS225 2026 Here, our employees don’t just have jobs,... ...comprehensive pay and benefits package that rewards...Work at officeLocal areaVisa sponsorship
$69k
...Description Job Description Remote Insurance Sales Representative | Flexible Schedule |... ...with stock options Comprehensive benefits package including medical, dental, and... ...Ongoing training and mentorship from experienced managers High-quality leads provided...Remote jobWork from homeFlexible hours- Love shoes? Love helping people? Join our team at Shoe Station at Rogan's! We're looking for a friendly, enthusiastic Store Associate who enjoys creating great experiences for customers. If you have strong people skills, a positive attitude, and can handle basic math...Part timeFlexible hoursShift workWeekend workAfternoon shift
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Experienced Sales Executive - Employee Benefits. Be the first to apply!
- food service sales representative Madison, WI
- group sales representative Madison, WI
- software sales executive Madison, WI
- roofing sales representative Madison, WI
- sales specialist Madison, WI
- senior sales representative Madison, WI
- commercial specialist Madison, WI
- outside sales representative Madison, WI
- new home sales consultant Madison, WI
- virtual sales representative Madison, WI






