Outside Sales Representative at Omada.AI

Chicago, Illinois, United States -

Full Time

Start Date

Immediate

Expiry Date

19 Sep, 26

Salary

100000.0

Posted On

21 Jun, 26

Experience

0 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Outside Sales, Lead Generation, Cold Calling, CRM Management, Relationship Building, Communication, Prospecting, Closing

Industry

technology;Information and Internet

Description

Compensation: $20/hr + uncapped commission ($200 per close). Top performers can earn up to $100K Employment type: 1099 Independent Contractor position / Freelance Schedule: Up to 40 hours a week Work type: Remote (this is NOT a work-from-home position). Some field work and some computer time. Location: Your local city, must reside in the United States The Opportunity AI is changing everything. Small businesses deserve to benefit. Right now, the salons, restaurants, gyms, coffee shops, and local shops and services that give every community its character are being left behind. They can't afford big marketing agencies. They don't have time to learn new tools. And most of the technology being built isn't being built for them. Here's the thing: small business owners aren't sitting around clicking ads looking for solutions. They're heads-down running their businesses. They buy from people they trust — and that's exactly what our Territory Partners become, someone they can trust. Omada.ai is changing the game — and we need people on the ground to help lead the charge. We're hiring Outside Sales Representatives / Territory Partners who are hungry, people-first, and genuinely excited about AI and what it can do for small businesses. In return, we'll put you on the front lines of one of the most important technology shifts of our lifetime, teach you everything you need to know, and pay you very well to do it. This is your chance to be part of the AI revolution — not by staring at a screen, but by walking into your community and making a real difference for real people. What you’ll do You'll be the face of Omada in your area — connect with local businesses, starting conversations, and showing owners how our AI platform can handle their marketing while they focus on running their business. You probably already know places like these. You eat at them, get your hair cut at them, and work out at them. Every one of them is trying to grow, and every one of them is struggling to keep up with technology — and you're showing up with a solution built specifically for them. Your week looks like this: Identify 10–50 businesses in your area using Omada's Route Planner Start the conversation in person or on the telephone, and ask a few clarifying questions Show a few examples of Omada right there on your phone or tablet Offer a free trial — no risk for them. Your trials are your leads Use our CRM HubSpot to track, follow up, follow up, follow up, and close When they convert to a paid subscription, you earn $200 Most of our Territory Partners close their first trial within the first week, and 3+ per week after that. Where this can take you We're building something big — and we promote from within. Top Territory Partners can move into team lead, city manager, and regional roles as we grow. If you want to build a real career at the intersection of AI and sales, this is where it starts. Requirements Hungry, self-motivated, and comfortable walking into a room Genuinely excited about AI and what it can do for small businesses Strong communicator who connects with people quickly No prior sales experience required — we'll teach you everything Must reside in the United States Must be 18 years of age or older Bonus: sales experience; experience working with small business owners This role is well-suited for Hunter sales reps who can develop their own book of business and want to earn uncapped commissions and a short sale cycle College grads or students who want to build sales skills and make real money Anyone tired of pure commission work but still wants serious upside About Omada.ai Omada is on a mission to help Main Street and local high streets win. We're building the largest organic growth platform for small businesses — a fully managed, AI-powered marketing team that grows SMBs end-to-end, without spending a dollar on paid ads. Founded by experienced operators and backed by world-class investors, including HubSpot, we're one of the fastest-growing AI companies in the country — and we're just getting started. Ready to start? Apply now. We're hiring in select cities and looking for people ready to start immediately.

Responsibilities

Identify and connect with local small businesses to demonstrate how the AI platform can automate their marketing. Manage the sales pipeline from initial contact and free trial offer to final paid subscription conversion using HubSpot.