B2B Sales Representative - With Upfront Commissions and Recurring Income

B2B Advertising Sales Representative – Upfront & Recurring Commissions

Already Selling to Local Businesses? Add Another Income Stream!

With the holiday season approaching, now is an ideal time to connect with local businesses looking to promote seasonal specials, attract customers, and increase their visibility.

Company: My Zip Ads LLC

Location: Chicagoland, Illinois – Flexible / Local Outside Sales

Compensation: 100% Commission-Based | No Base Salary

Position: Independent Sales Representative opportunity, subject to applicable worker-classification requirements

My Zip Ads is expanding throughout Chicagoland, and we’re looking for motivated, experienced B2B sales professionals who want to earn upfront commissions while building a portfolio of advertisers with long-term recurring income potential.

If you’re already meeting with restaurant owners, contractors, retailers, professional offices, or other local businesses, this could be a natural addition to the services you already offer.

You don’t need to abandon your existing business or start building relationships from scratch. Introduce a valuable advertising opportunity to businesses you already know while continuing to develop your existing sales activities, provided your current agreements permit it.

Whether you’re an established independent sales representative or an experienced salesperson looking for a new opportunity, My Zip Ads offers a flexible way to expand your earning potential.

What Is My Zip Ads?

My Zip Ads is a shared direct-mail advertising program designed to help local businesses reach approximately 10,000 residential households per monthly mailing.

Our oversized 9” × 12” postcards feature multiple local advertisers, allowing businesses to share printing and mailing costs while benefiting from repeated exposure in their communities.

Our advertising program offers:

• Monthly direct-mail advertising
• Category-exclusive advertising opportunities
• Affordable multi-month advertising packages
• Consistent visibility among local households
• Additional printing, graphic design, and marketing services

Our initial target communities include Arlington Heights, Des Plaines, Mount Prospect, Morton Grove, and Niles, with plans to expand into additional Chicagoland markets.

Build Upfront Commissions, Recurring Income & Expand Into New Territories

Start with one mailing area. Build your advertiser portfolio. Then repeat the process in additional suburbs.

Unlike traditional one-time sales opportunities, My Zip Ads allows representatives to develop advertiser relationships that can generate additional commissions through renewals.

Each mailing area accommodates up to 16 standard advertising positions.

Example Using Our $6,000 Annual Advertising Plan

One Fully Sold Mailing Area

• $18,000 in upfront commissions
• Potential for $1,500 in monthly recurring commissions upon full renewal

Two Fully Sold Mailing Areas

• $36,000 in upfront commissions
• Potential for $3,000 in monthly recurring commissions upon full renewal

Three Fully Sold Mailing Areas

• $54,000 in upfront commissions
• Potential for $4,500 in monthly recurring commissions upon full renewal

The opportunity doesn’t have to stop there.

As My Zip Ads expands throughout Chicagoland, successful representatives may develop additional mailing areas, build new advertiser portfolios, and continue increasing their earning potential.

And while building those territories, representatives can continue earning upfront commissions from new qualifying sales.

These examples assume all 16 standard positions in each mailing area are sold as qualifying $6,000 annual plans. Recurring commissions begin upon qualifying renewals and are paid monthly over the renewed term, subject to the commission agreement. Actual sales, renewals, territory availability, and earnings are not guaranteed.

Additional Income Opportunities

My Zip Ads also provides printing, graphic design, and other business marketing services.

Representatives can earn additional commissions on qualifying sales involving:

• Business cards, brochures, flyers, and menus
• Postcards and direct-mail campaigns
• Banners, signage, and promotional materials
• Graphic design and branding services
• Other available marketing products and services

One business relationship can create multiple sales opportunities.

What You’ll Do

• Introduce My Zip Ads to local business owners and decision-makers
• Present advertising packages and explain the benefits of consistent direct-mail exposure
• Identify prospective advertisers and develop new business relationships
• Follow up with interested businesses and close advertising sales
• Build and maintain a portfolio of local advertisers
• Identify printing, design, and additional marketing opportunities
• Develop new mailing areas as expansion opportunities become available
• Manage your sales pipeline and maintain professional customer relationships

Who We’re Looking For

This opportunity is especially well-suited for professionals with experience in:

• B2B sales and business development
• Advertising and media sales
• Printing and promotional products
• Merchant services and payment processing
• Website and digital marketing sales
• Outside sales and local business account management

Existing relationships with local business owners are a major advantage.

Ideal candidates are self-motivated, professional, comfortable speaking with decision-makers, and capable of independently developing and managing their sales activities.

Compensation & Flexibility

• 100% commission-based compensation — no base salary
• $1,125 upfront commission per qualifying $6,000 annual advertising sale
• Monthly recurring commissions on qualifying annual-plan renewals
• Commissions on eligible shorter-term advertising packages, calculated according to the applicable commission schedule
• Additional commission opportunities from printing, graphic design, and other eligible services
• Opportunity to develop multiple Chicagoland mailing areas
• Flexible prospecting and local sales activities

This opportunity may be particularly appealing to established independent sales professionals looking to add another product to their existing offerings.

All compensation is subject to the written commission agreement. Actual earnings depend on qualifying sales, customer payments, renewals, and applicable commission terms. No earnings are guaranteed.

Why Join My Zip Ads?

We’re building a local advertising network designed to help businesses stay visible in their communities through consistent, affordable direct-mail marketing.

For the right sales professional, this isn’t simply about selling one advertisement.

It’s about building a portfolio of advertisers, developing multiple territories, and creating opportunities for recurring income as the business expands.

Apply Today

If you have experience selling to local businesses and are interested in a scalable, commission-based advertising opportunity, we’d like to hear from you.

Tell us about your sales background, the Chicagoland areas you serve, and the types of businesses you currently work with.

My Zip Ads LLC

www.MyZipAds.com

This is a commission-only opportunity. Any independent-contractor classification and compensation arrangement must comply with applicable federal, state, and local laws.

Pay: Up to $60,000.00 per year

Application Question(s):

• Do you currently have experience selling products or services directly to local business owners?

Yes / No

• Are you comfortable with a 100% commission-based opportunity with no guaranteed base salary?

Yes / No

• Do you currently have relationships with local businesses in the Chicagoland area?

Yes / No

Work Location: On the road