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 independent sales partners are the true face and heartbeat of our network. Tech alone cannot replace a handshake, so we provide the inventory, the digital catalog, and the logistics, while you build the local trust needed to grow your own book of business.

About The Opportunity

We are looking for motivated, highly driven independent contractors to take over and grow their own local sales territory in the Chicago Metro Area. As a 1099 Independent Sales Representative, you run your own business. You control your schedule, your methods, and your earning potential, backed by our easy-to-use phone app and a catalog of thousands of top-selling items.

Operating Your Territory: You will be targeting independent retailers across the Chicago Metro Area—convenience stores, gas stations, bodegas, liquor stores, smoke shops, and any independently owned business that sells CPG goods. If it's independently owned and you can get in touch with the decision-maker, they are a potential client.

• Independent Outreach: Walking into stores, getting past the counter, and pitching the RepRally platform directly to business owners.

• Relationship Management: Prospecting new stores, earning the owner's trust, and managing your own client relationships.

• Driving Volume: Using our mobile app right in the aisle to facilitate initial orders, then actively managing your accounts to secure continuous, high-volume re-orders.

What We Look For

• Sales or Hustle Experience: Experience in B2B sales, delivery routes, or independent contracting 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 close the account.

• Total Independence: You love the freedom of running your own day and executing your own sales strategy without a boss watching over your shoulder.

• The Basics: You operate as your own entity, meaning you provide your own valid driver's license, a reliable vehicle to get around, and a smartphone with a data plan.

Compensation & The RepRally Sales Ladder

As an independent contractor, your earnings are tied directly to your results. We operate on a transparent, merit-based tier system: Bronze, Silver, Gold, Platinum, and Diamond.

Every partner starts their journey on the RepRally Sales Ladder. The vast majority of our partners begin in our Bronze or Silver tiers to master the catalogue and build their initial book of business, with starting placements tailored to your background.

• Bronze & Silver Tiers (Entry to Intermediate): Perfect for hungry reps building their territory. Earn lucrative flat-rate commissions (up to 7% on every dollar sold) or unlock weekly activity-based stipends. Typical earnings range up to $100 – $1,300+ per week depending on the time you choose to invest.

• Gold, Platinum & Diamond Tiers (Advanced): Built for top-tier closers with an established pipeline, and extensive experience in the industry. Unlock weekly performance base targets, territory expansion bonuses, multi-brand incentives, and uncapped commissions. Top performers at these levels earn up to $750 – $3,000+ per week.

• Rapid Upward Mobility: We do not care about tenure; we care about revenue. Consistently hit your sales milestones and you will automatically unlock the next payout tier. You are in total control of your earning potential.

Our Fast-Track Partnership Process

We respect your time. We do not do corporate ghosting, make you wait weeks for an answer, or force you through tedious interview rounds. We review profiles rapidly so you can hit the field and start generating revenue immediately.

• Submit Your Resume: No cover letters required.

• Fast-Track Review: Our team evaluates your background to determine your best starting position on the Sales Ladder.

• Same-Day Agreements: We review applications daily. If you are a strong fit, you will receive your 1099 independent contractor agreement and tier placement via email the exact same day you apply.

• Start Selling Immediately: Sign your agreement, complete your self-service onboarding in our app, and launch your territory.