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Remote Sales Representative Jobs in Middleton, WI

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)

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:

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)

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)

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:

Danaher

Inside Sales Representative (REMOTE)

Madison, WI · On-site +1

$33.65 - $43.27/hr

The Inside Sales Representative is a quota-carrying seller responsible for full-cycle sales of ... We recognize the benefits of flexible, remote working arrangements for eligible roles and are ...

Danaher

Inside Sales Representative (REMOTE)

Madison, WI · On-site +1

$33.65 - $43.27/hr

The Inside Sales Representative is a quota-carrying seller responsible for full-cycle sales of ... We recognize the benefits of flexible, remote working arrangements for eligible roles and are ...

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All JobsSales Representative JobsRemote Sales Representative JobsRemote Sales Representative Jobs in Middleton, WI

Remote Sales Representative information

See Middleton, WI salary details

$23.1K

$77K

$142K

How much do remote sales representative jobs pay per year?

As of Aug 11, 2026, the average yearly pay for remote sales representative in Middleton, WI is $76,953.00, according to ZipRecruiter salary data. Most workers in this role earn between $53,700.00 and $93,300.00 per year, depending on experience, location, and employer.

What is a remote sales representative?

A Remote Sales Representative is a sales professional who works from a location outside of a traditional office, often from home or another remote setting. They are responsible for reaching out to potential customers, presenting products or services, and closing sales, primarily through phone calls, emails, and virtual meetings. This role requires strong communication skills, self-motivation, and the ability to work independently while meeting sales targets. Remote sales representatives often use digital tools and CRM software to manage leads and track sales activities. The flexibility of this job allows companies to tap into a wider talent pool and enables employees to work from virtually anywhere.

What does a remote sales representative do?

Remote sales representatives communicate with customers on a regular basis to sell one product or multiple services via phone calls. These professionals do the same job as regular sales reps but with the option of making commission and performing responsibilities from home. As a remote sales rep, you take the initiative to locate and contact the customer, using persuasive techniques and your excellent interpersonal skills to negotiate and secure sales. You focus on developing each client relationship to foster opportunities for future business. In this role, you also establish sales targets and outcomes, setting deadlines and coordinating sales efforts among team members.

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

To thrive as a Remote Sales Representative, you need strong sales acumen, product knowledge, and typically a background in business or communications. Familiarity with CRM software like Salesforce, video conferencing tools, and digital communication platforms is essential. Outstanding self-motivation, resilience, and effective virtual communication skills distinguish top performers in this remote environment. These abilities are vital for building client relationships, meeting sales targets, and maintaining productivity outside a traditional office setting.

Can a remote sales representative work remotely?

Yes, remote sales representatives typically work from home or other remote locations, using digital communication tools like email, phone, and video conferencing to connect with clients and manage sales activities. Their ability to work remotely depends on company policies, job requirements, and the need for in-person meetings or events.

What are some common challenges faced by remote sales representatives, and how can they be effectively managed?

Remote Sales Representatives often encounter challenges such as building rapport with clients without face-to-face interaction, staying motivated while working independently, and managing time across different time zones. To overcome these obstacles, it's important to leverage video calls and personalized communication tools, establish a structured daily routine, and use CRM software to keep track of leads and follow-ups. Regular virtual team meetings and ongoing training can also foster a sense of connection and ensure alignment with team goals.
More about Remote Sales Representative jobs
What job categories do people searching Remote Sales Representative jobs in Middleton, WI look for? The top searched job categories for Remote Sales Representative jobs in Middleton, WI are:
What cities near Middleton, WI are hiring for Remote Sales Representative jobs? Cities near Middleton, WI with the most Remote Sales Representative job openings:
Remote Sales Representative jobs near you
Infographic showing various Remote Sales Representative job openings in Middleton, WI as of August 2026, with employment types broken down into 56% Full Time, 21% Part Time, and 23% Contract. Highlights an 100% Remote job distribution, with an average salary of $76,953 per year, or $37 per hour.

Remote Sales Representative

Cha & Associates, Inc. - American Family Insurance

Madison, WI • Remote

$50K - $60K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 22 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.