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Remote Sales Rep ~ Jobs in Madison, WI (NOW HIRING)

Lone Star Careers

Remote Sales Rep

Madison, WI · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible ... Sales or customer service experience is helpful but not required Qualifications * Laptop or desktop ...

Empire State Careers

Remote Sales Rep

Madison, WI · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers ... Sales or customer service experience is helpful but not required Qualifications * Laptop or desktop ...

InsuraTec

Sales Representative (Remote)

Verona, WI · Remote

We're looking for driven individuals to join our team as Sales Representatives in a fully remote, flexible role that provides significant financial growth opportunities. Key Responsibilities:

InsuraTec

Sales Representative (Remote)

Oregon, WI · Remote

We're looking for driven individuals to join our team as Sales Representatives in a fully remote, flexible role that provides significant financial growth opportunities. Key Responsibilities:

InsuraTec

Sales Representative (Remote)

Waunakee, WI · Remote

We're looking for driven individuals to join our team as Sales Representatives in a fully remote, flexible role that provides significant financial growth opportunities. Key Responsibilities:

InsuraTec

Sales Representative (Remote)

Portage, WI · Remote

We're looking for driven individuals to join our team as Sales Representatives in a fully remote, flexible role that provides significant financial growth opportunities. Key Responsibilities:

InsuraTec

Sales Representative (Remote)

Madison, WI · Remote

We're looking for driven individuals to join our team as Sales Representatives in a fully remote, flexible role that provides significant financial growth opportunities. Key Responsibilities:

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All JobsSales Rep ~ JobsRemote Sales Rep ~ JobsRemote Sales Rep ~ Jobs in Madison, WI

Remote Sales Rep information

See Madison, WI salary details

$23.2K

$77.3K

$142.6K

How much do remote sales rep ~ jobs pay per year?

As of Sep 8, 2026, the average yearly pay for remote sales rep ~ in Madison, WI is $77,266.00, according to ZipRecruiter salary data. Most workers in this role earn between $53,900.00 and $93,700.00 per year, depending on experience, location, and employer.

What is a remote sales rep ~?

A Remote Sales Rep is responsible for selling products or services while working outside of a traditional office setting, usually from home. The job involves reaching out to potential customers, building relationships, and closing sales through phone calls, emails, and virtual meetings. Successful remote sales reps must be self-motivated, have strong communication skills, and be comfortable using digital tools to manage leads and track progress. This role often offers flexibility in work hours and location, making it ideal for independent, goal-driven individuals.

What are the key skills and qualifications needed to thrive as a remote sales rep ~?

To thrive as a Remote Sales Rep, you need strong communication, negotiation, and customer relationship management skills, often supported by a background in sales or business and a proven track record of meeting targets. Familiarity with CRM platforms like Salesforce or HubSpot, as well as proficiency in video conferencing and email outreach tools, is typically required. Exceptional self-motivation, time management, and problem-solving abilities help individuals excel in this remote environment. These skills are crucial for building client trust, closing deals, and consistently achieving sales goals while working independently.

What are some common challenges faced by remote sales reps ~, and how can they be addressed?

One common challenge for Remote Sales Reps is maintaining consistent communication and engagement with prospects and clients without the benefit of in-person meetings. Staying motivated and organized while working independently can also be demanding, as there are fewer immediate touchpoints with managers or team members. To address these challenges, it's important to establish a structured daily routine, leverage collaborative tools for regular check-ins, and actively participate in virtual team meetings. Successful reps also set clear goals for themselves and use CRM systems to track and nurture leads efficiently.

Can a remote sales representative work remotely?

Yes, a remote sales representative typically works remotely, using digital communication tools like email, phone, and video conferencing to connect with clients and manage sales activities. Many companies offer flexible or fully remote positions for sales roles, provided the employee has a suitable home office setup and strong communication skills.

How much do remote sales representatives make?

Remote sales representatives typically earn an average annual salary ranging from $40,000 to $70,000, with top performers earning over $100,000 including commissions and bonuses. Compensation often depends on experience, industry, sales skills, and the company's commission structure.

What are the most commonly searched types of Sales Rep ~ jobs in Madison, WI?

The most popular types of Sales Rep ~ jobs in Madison, WI are:

What are popular job titles related to Remote Sales Rep ~ jobs in Madison, WI?

For Remote Sales Rep ~ jobs in Madison, WI, the most frequently searched job titles are:

What job categories do people searching Remote Sales Rep ~ jobs in Madison, WI look for?

The top searched job categories for Remote Sales Rep ~ jobs in Madison, WI are:

What cities near Madison, WI are hiring for Remote Sales Rep ~ jobs?

Cities near Madison, WI with the most Remote Sales Rep ~ job openings:

Remote Sales Rep jobs near you
Infographic showing various Remote Sales Rep ~ job openings in Madison, WI as of September 2026, with employment types broken down into 76% Full Time, 23% Part Time, and 1% Contract. Highlights an 82% Physical, 1% Hybrid, and 17% Remote job distribution, with an average salary of $77,266 per year, or $37.1 per hour.

Remote Sales Representative

Madison, WI • Remote

Cha & Associates, Inc. - American Family Insurance
See more jobs at Cha & Associates, Inc. - American Family Insuranceexternal

$50K - $60K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 20 days ago

Job description

Benefits:
  • Life insurance
  • 401(k) matching
  • Bonus based on performance
  • Dental insurance
  • Health insurance
  • Opportunity for advancement
  • Paid time off
  • Training & development
  • Vision insurance

Grow Your Sales Career with a Trusted Agency
Are you a motivated sales professional who enjoys building relationships, achieving goals, and helping people protect what matters most? Are you looking for an opportunity where your hard work is rewarded and your earning potential is driven by your success?
Cha & Associates Inc. is seeking an Insurance Sales Representative to join our growing American Family Insurance agency in Madison, WI. This is a sales-focused role designed for someone who enjoys prospecting, developing new business, and closing opportunities while delivering an outstanding customer experience.
If you're competitive, driven, and excited to build a rewarding career with a respected local agency, we'd love to hear from you.
Why Join Cha & Associates?
  • Uncapped commission opportunities to take ownership and control of your own income.
  • Performance-based bonuses and incentives.
  • Ongoing training, coaching, and professional development.
  • Established agency with a loyal customer base and strong community reputation.
  • Supportive, collaborative team environment.
  • Opportunities for career growth and advancement.
What You'll Do
As an Insurance Sales Representative, you'll focus on generating new business while helping clients find personalized insurance solutions that fit their needs.
Responsibilities
  • Prospect and develop new business through referrals, networking, community outreach, and lead follow-up.
  • Build relationships with prospective clients and earn their trust through consultative conversations.
  • Conduct needs-based insurance reviews and recommend appropriate coverage solutions.
  • Educate customers on insurance products, policy features, discounts, and available coverage options.
  • Follow up consistently with prospects and maintain an active sales pipeline.
  • Cross-sell and bundle insurance products to provide comprehensive protection.
  • Meet and exceed individual sales goals and agency production objectives.
  • Maintain accurate customer records and sales activity within agency systems.
What We're Looking For
  • Previous sales experience strongly preferred.
  • Insurance sales experience is a plus but not required.
  • Property & Casualty Insurance License is preferred or willingness to obtain after hire.
Ideal Candidate
  • Confident, outgoing, and relationship-driven.
  • Excellent communication and interpersonal skills.
  • Self-motivated with a strong desire to achieve goals.
  • Competitive mindset and results-oriented attitude.
  • Organized with strong time-management skills.
  • Comfortable prospecting, making outbound calls, and asking for the sale.
  • Positive, coachable, and eager to continue learning.
Who Thrives in This Role?
Our most successful sales professionals enjoy meeting new people, creating opportunities, and building lasting relationships. They embrace challenges, stay motivated by goals, and take pride in helping clients make informed decisions while growing their own careers.
At Cha & Associates, we believe success comes from investing in great people. We'll provide the training, support, and resources you need to grow your skills, maximize your earning potential, and build a long-term career with one of the most trusted names in insurance.
Apply today and join the Cha & Associates Inc. team in Madison, WI!

This is a remote position.