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

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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 May 28, 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 the key skills and qualifications needed to thrive as an Insurance Sales professional working weekends, and why are they important?

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 are Insurance Sales Weekend jobs?

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 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 most commonly searched types of Insurance Sales jobs in Madison, WI? The most popular types of Insurance Sales jobs in Madison, WI are:
What cities near Madison, WI are hiring for Insurance Sales Weekend jobs? Cities near Madison, WI with the most Insurance Sales Weekend job openings:
Insurance Sales Weekend jobs near you

Insurance Sales Rep

Prairie Land Insurance Agency

Madison, WI • On-site

$40K - $60K/yr

Full-time

Medical, Retirement, PTO

This job post has expired 1 day ago. Applications are no longer accepted.

Job description

Prairie Land Insurance Agency is a family-owned agency with deep roots in the community, founded in 1986 and proudly serving clients for nearly four decades. Today, the agency is a close-knit, three-person team where collaboration, trust, and relationships matter. We believe enjoying your work shows through in every client interaction. Our focus is not on being the biggest agency, but on being one of the best for both clients and employees.

We are seeking an Insurance Sales Representative who enjoys helping people, building long-term relationships, and working as part of a supportive team. This is not a high-pressure or cutthroat sales environment. Sales here is collaborative, relationship-focused, and built on trust. You will work closely with clients to protect what matters most while growing a book of business you can be proud of.

  • First-year earnings of $40,000 to $60,000
  • Paid commissions on renewals
  • Health and disability insurance 100% paid by employer
  • Paid time off, paid sick leave, and paid holidays
  • 401k with 3% employer match
  • Office snacks and coffee

If you want a welcoming workplace where sales is about helping people, apply today!


Benefits

Annual Base Salary + Commission + Bonus Opportunities

Paid Time Off (PTO)

Flexible Schedule

Health Insurance

Disability Insurance

Tuition Reimbursement

Career Growth Opportunities

Evenings off

Weekends off

Bonus Opportunities

Paid on Renewals

Licensing Assistance

Work-Life Balance

Holidays Off

Paid Holidays

401k Plan

Professional Development

Mentorship

Continuing Education Opportunities

Performance Bonuses

Professional Work Environment

Paid Parking

Equipment Provided

Office Snacks and Coffee

Paid Sick Leave

Personal Workspace


Responsibilities
  • Prospect, quote, and sell personal and commercial lines policies
  • Develop new business through referrals, inbound leads, and outreach
  • Identify cross-sell and upsell opportunities
  • Build and maintain strong client relationships
  • Work with carriers to secure competitive coverage

Requirements
  • Active insurance license
  • Consultative, relationship-first sales mindset
  • Strong communication skills, written and verbal
  • Organized with strong attention to detail
  • Self-motivated and team-oriented
  • Customer-first attitude focused on trust and long-term value