Independent Territory Sales Representative – Chicago, IL

What is RepRally?

RepRally is an AI-powered online marketplace that connects independent retailers directly with thousands of popular Consumer Packaged Goods (CPG) brands. Normally, these stores are forced to buy from giant middleman distributors who charge high prices. We fix that by combining our digital platform with the unstoppable power of real, face-to-face relationships. While we have an online platform, our field sales representatives are the true face and heartbeat of our business. Tech alone cannot replace a handshake, so we provide the inventory and data tools while our independent partners build the local trust needed to grow the network.

About the Opportunity

We are looking for motivated, hard-working independent sales partners to take over and grow their own local sales area in the Chicago Metro Area. This is a 1099 independent contractor role where you bring the energy to talk to independent stores and close the sales, backed by our easy-to-use phone app, field support, and catalog of thousands of top-selling items.

Your Daily Work Involves:

You will be visiting independent retailers in your area—convenience stores, gas stations, bodegas, liquor stores, smoke shops, and any independent business that sells CPG goods (snacks, drinks, etc.). If it's independently owned and you can get in touch with the decision-maker, you can sell to them. We do not sell to large corporate chains (e.g., Walmart, Target).

Your typical work involves:

• Walking In & Pitching: Walking into stores cold, getting past the counter, and pitching RepRally directly to the decision-maker.

• Building Relationships: Hitting the phones and dropping by in person to scout out new stores, earn the owner's trust, and set appointments.

• Placing Orders & Driving Volume: Using our mobile app right in the aisle to lock in the first sale, then actively managing the account to secure continuous, high-volume re-orders.

What We Look For

• Sales or Hustle Experience: Experience in delivery routes, door-to-door sales, or retail is great—but a refusal to give up is what actually matters.

• Comfort with Cold Pitching: You do not take "no" personally. You are comfortable walking into a store cold and following up until you get the win.

• Independent Work Style: You love the freedom of running your own day without a manager watching over your shoulder.

• The Basics: You need a valid driver's license, a reliable vehicle to get around, and a smartphone with a data plan.

Uncapped Earning Potential

Our payout plan features weekly bonuses and unlimited commissions to reward fast work. Earnings are processed every single week.

• Territory Expansion Bonus: Earn an extra weekly cash bonus when you hit your milestones for setting up and activating new stores.

• Performance Milestone Bonus: Earn an extra weekly cash bonus for hitting your total weekly sales volume goals.

• Unlimited Commissions: Earn a percentage on every single dollar you bring in above your weekly baseline goal—with absolutely no limits on what you can make.

• Multi-Brand Incentives: Earn an extra cash bonus on your weekly payout cycle every time a store places an order that stacks multiple different brands into one ticket.

Our Fast-Track Sign-Up Process (3 to 7 Days)

We respect your time. We do not do corporate ghosting or make you wait weeks for an answer. We review applications fast so you can get on the road and start making money immediately.

1. Apply & Check Your Texts: Within minutes of applying, you will get a text message with a link to your structured video interview.

2. Interview on Your Own Time: Skip the hassle of scheduling a live meeting. Record a quick, 15-minute video interview answering a few questions on your smartphone or your laptop computer whenever you are ready.

3. Real Help via Text: If you get stuck or have questions, just reply directly to our text message. We have real people standing by to text you back.

4. Fast Final Decision: We review submissions instantly. If you are a strong fit, you will get a formal offer within minutes. Otherwise, we will text you back within 24 hours—either way, you will never be left waiting around.