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

HealthMarkets, Inc.

Insurance Sales Agent

Madison, WI · On-site

Insurance Sales Agent Insurance Sales Agent Location: Madison, Wisconsin Job Number HM2025-0837 Date posted 02/02/2025 Join Us HealthMarkets Overview If you're looking for an exciting opportunity ...

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All JobsInsurance Sales JobsInsurance Sales Weekend JobsInsurance Sales Weekend Jobs in Madison, WI

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 Sep 11, 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 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 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.

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.

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.

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 managing flexible schedules to accommodate client appointments outside of full-time work hours.

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 turnover.

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:

Insurance Sales Weekend jobs near you

Insurance Sales

Waunakee, WI

Farmers Insurance Agencies
See more jobs at Farmers Insurance Agenciesexternal

Full-time

Posted 7 days ago

Farmers Insurance rating

7.5

Company rating: 7.5 out of 10

Based on 339 frontline employees who took The Breakroom Quiz

Job description

As an insurance producer working for a Farmers agency owner, you can assist prospective and existing customers in your community with products and services they need.


Compensation for this position is solely up to the Farmers agency owner, which may include base salary, base salary plus commission, or commission only arrangements. If commission is part of the compensation for this position, the agency owner can provide you a list of applicable insurance and insurance-related products along with the commission rates for which you can be compensated.


Responsibilities

Common Responsibilities for Appointed Insurance Producers

  • Network and develop leads
  • Establish contact with prospects and schedule appointments
  • Meet with prospective customers
  • Meet with existing customers to perform policy reviews
  • Conduct sales presentations
  • Solicit referrals

Requirements

Qualifications for Appointment

  • Must work for a Farmers agency owner
  • Must be licensed in the applicable state
  • Ability to pass a background check

What Farmers Insurance employees say

Pay

Benefits

Hours and flexibility

Workplace

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