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Insurance Sales Weekend Jobs in Madison, WI (NOW HIRING)

The Opportunity As a Financed Agent with Rural Mutual Insurance, you will build and grow a book of business across Wisconsin. This is not a traditional sales job with a quota and a manager looking ...

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The Opportunity As a Financed Agent with Rural Mutual Insurance, you will build and grow a book of business across Wisconsin. This is not a traditional sales job with a quota and a manager looking ...

New

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Insurance Sales Specialist

Verona, WI · On-site

$40K - $60K/yr

We are seeking an Insurance Sales Specialist to join our team! You will be responsible for expanding the company's book of business by selling various types of insurance policies to new and existing ...

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Insurance Sales Specialist

Verona, WI · On-site

$40K - $60K/yr

We are seeking an Insurance Sales Specialist to join our team! You will be responsible for expanding the company's book of business by selling various types of insurance policies to new and existing ...

New

Be Seen First

Insurance Sales Specialist

Verona, WI · On-site

$40K - $60K/yr

We are seeking an Insurance Sales Specialist to join our team! You will be responsible for expanding the company's book of business by selling various types of insurance policies to new and existing ...

New

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Insurance Sales Weekend information

See Madison, WI salary details

$29.7K

$92.8K

$141.6K

How much do insurance sales weekend jobs pay per year?

As of Aug 5, 2026, the average yearly pay for insurance sales weekend in Madison, WI is $92,819.00, according to ZipRecruiter salary data. Most workers in this role earn between $69,000.00 and $116,900.00 per year, depending on experience, location, and employer.

What are some common challenges faced by insurance sales professionals working on weekends, and how can they be addressed?

Insurance sales professionals working on weekends often face challenges such as reaching decision-makers who may be unavailable or less willing to discuss policies outside regular business hours. However, weekends can also provide opportunities to connect with clients who are too busy during the week. Successful agents typically adapt by being flexible with their scheduling, offering virtual consultations, and focusing on relationship-building. Proactive communication and clear follow-ups are key strategies to overcome these challenges and maximize weekend productivity.

Can I sell insurance on weekends?

Insurance sales jobs often offer flexible schedules, and many agents sell policies on weekends to accommodate clients' availability. However, specific working hours depend on the employer, licensing requirements, and whether the role involves in-person or remote sales. It is common for insurance agents to work outside traditional weekday hours, including weekends, especially during busy periods or for client convenience.

Can I do insurance sales as a side hustle?

Insurance sales can often be pursued as a side hustle, as many agents work part-time or freelance to supplement their income. Success typically requires obtaining relevant licenses, such as a state insurance license, and dedicating flexible hours to client meetings and sales activities.

What is the difference between Insurance Sales Weekend vs Insurance Agent?

AspectInsurance Sales WeekendInsurance Agent
CertificationsOften no formal certifications required, but some knowledge of insurance products helpsRequires state licensing and certifications to sell insurance
Work EnvironmentTemporary, event-based, often part-time or seasonalFull-time or part-time, office or client-facing settings
Employer & Industry UsageUsed by insurance companies for promotional or sales eventsEmployed directly by insurance companies or agencies to sell policies
Search & Comparison IntentPeople looking for short-term sales opportunities or event-based rolesIndividuals seeking ongoing sales careers in insurance

Insurance Sales Weekend roles are typically short-term, event-based sales opportunities that may not require formal licensing, whereas Insurance Agents are licensed professionals who sell insurance policies on a regular basis. The roles differ mainly in duration, certification requirements, and employment structure, with Insurance Agents pursuing continuous careers in the industry.

What are the key skills and qualifications needed to thrive as an insurance sales professional working weekends?

To thrive as an Insurance Sales professional on weekends, you need strong sales abilities, knowledge of insurance products, and typically a state-specific insurance license. Familiarity with CRM software, online quoting tools, and digital communication platforms is often required. Excellent interpersonal skills, self-motivation, and the ability to build trust quickly help you stand out in this customer-facing role. These skills ensure you can effectively engage clients, close sales, and maintain compliance in a competitive, time-sensitive environment.

Why do most insurance sales weekend agents quit?

Most insurance sales weekend agents quit due to the challenging nature of the job, which often involves high rejection rates, inconsistent income, and the need for strong sales skills. The part-time schedule and pressure to meet sales targets can also lead to burnout and job dissatisfaction.

What is an insurance sales weekend job?

Insurance Sales Weekend jobs involve selling insurance policies—such as auto, health, life, or home insurance—primarily during weekends. These roles may suit individuals seeking part-time or flexible work schedules, such as students or those supplementing existing income. Weekend insurance sales agents engage with potential clients, assess their insurance needs, explain policy options, and help customers choose the best coverage. The role often includes a mix of phone, online, and in-person interactions, and may involve meeting sales targets or earning commission.
What are the most commonly searched types of Insurance Sales jobs in Madison, WI? The most popular types of Insurance Sales jobs in Madison, WI are:

Full-time

Re-posted 10 days ago


Job description

Description

We are looking for an Insurance Sales Associate to join our team in our Appleton, Wisconsin  office.  This is not a remote position.

We're Hiring Immediately!

 

As an Insurance Sales Associate, you will work alongside with and support a Comparion Insurance Sales Agent in profitable growth through new business sales and customer retention. Your ability to listen and empathize are key in being the initial contact for our customers. Success in this role will require building a strong local network and in-person relationship in the community. 

Working for Comparion Insurance Agency, a Liberty Mutual company, means working for a company that's committed to advancing an inclusive environment. We do that through leadership development programs aimed at advancing, engaging, and retaining under-represented talent and our Employee Resource Groups, which strengthen our inclusive workplace, enhance personal development, and provide ways for employees to connect, learn and engage.

Ready to find out what it means to work for an agency that is backed by Liberty Mutual-a Fortune 100 company that's committed to putting people first, acting responsibly and making things better?

Responsibilities:

  • Utilize consultative sales techniques to prospect and initiate new business sales.
  • Assists in the processing of new business, including contacting customers to finalize sales and service transactions.
  • Identifies cross selling opportunities for Sales Agent.
  • Contributes to and executes a marketing plan with the Sales Agent.
  • Identifies mass marketing prospects through existing book of business and community prospecting opportunities.
  • Meet monthly goals for new business sales.
  • Completes follow-ups on new policies in order to keep retention level high and capitalize cross-selling opportunities.
  • Coordinates activities with other departments to ensure quality customer service
  • Acts as initial contact in addressing customer concerns regarding establishment of policies and new account status.
  • Unlicensed candidates will be enrolled in a new hire training class once they begin working for Comparion.  The training includes a licensing training program in which Comparion covers the cost of training materials and exam fees.
External Qualifications
  • High School Degree
  • 1-2 years of relevant sales experience preferred 
  • Exceptional written and verbal communication skills
  • Ability to handle common objections and educate customers in a consultative manner
  • Demonstrated self-starter, motivated to learn and grow in a professional sales organization
  • Professional business acumen, strong presence and confidence
  • Resourceful team player that can contribute and accept new ideas
  • A state insurance license-or willingness to earn one with training and support-in Property & Casualty, and Life
About Us

Pay Philosophy: The typical starting salary range for this role is determined by a number of factors including skills, experience, education, certifications and location. The full salary range for this role reflects the competitive labor market value for all employees in these positions across the national market and provides an opportunity to progress as employees grow and develop within the role. Some roles at Liberty Mutual have a corresponding compensation plan which may include commission and/or bonus earnings at rates that vary based on multiple factors set forth in the compensation plan for the role.At Liberty Mutual, our goal is to create a workplace where everyone feels valued, supported, and can thrive. We build an environment that welcomes a wide range of perspectives and experiences, with inclusion embedded in every aspect of our culture and reflected in everyday interactions. This comes to life through comprehensive benefits, workplace flexibility, professional development opportunities, and a host of opportunities provided through our Employee Resource Groups. Each employee plays a role in creating our inclusive culture, which supports every individual to do their best work. Together, we cultivate a community where everyone can make a meaningful impact for our business, our customers, and the communities we serve. We value your hard work, integrity and commitment to make things better, and we put people first by offering you benefits that support your life and well-being. To learn more about our benefit offerings please visit: https://www.libertymutualgroup.com/about-lm/careers/benefitsLiberty Mutual is an equal opportunity employer. We will not tolerate discrimination on the basis of race, color, national origin, sex, sexual orientation, gender identity, religion, age, disability, veteran's status, pregnancy, genetic information or on any basis prohibited by federal, state or local law.Fair Chance Notices

  • California
  • Los Angeles Incorporated
  • Los Angeles Unincorporated
  • Philadelphia
  • San Francisco
Employment Type: FULL_TIME