Field sales representative Jobs in Chicago, IL

Company: Omada.ai
Compensation: Base + uncapped commission ($200–$250 per close) | Top performers earn $100K+ in year one — and that's just the floor.
Schedule: Full-time
Location: Your local city (must reside in the United States)

This isn't a sales job. It's a leadership track disguised as one.

Let's skip the fluff. You've sold before. You've hit quota, probably carried a team or two, and you already know you're good at this. The question isn't whether you can sell — it's whether what you're selling actually matters, and whether the company behind it is going somewhere worth going.

Here's your answer.

The Market

AI is the biggest shift in business since the internet — and right now, the companies worth trillions are building it for enterprises. Nobody's building it for the salon on the corner, the gym down the block, the restaurant you eat at every week. These owners are drowning in marketing they don't have time for, tools they can't figure out, and agencies they can't afford.

Omada built the solution. You're going to be the one who puts it in their hands.

What You'll Actually Do

You're not sitting in a cubicle dialing strangers. You're in the field — your city, your territory, face-to-face with business owners who need exactly what you're offering.

Your day: pick 10–50 businesses using Omada's Route Planner. Walk in. Start a conversation. Pull up the platform on your phone and show them what their marketing could look like — built by AI, running while they sleep. Offer a 14-day free trial. No risk for them. When they convert, you earn $200–$250. Per close. Uncapped.

Most partners close their first two trials in week one. Strong reps close 10+ per week. You do the math on what that looks like at $250 a pop.

Why This Role Is Different

We're not hiring you to be a rep forever. We're hiring you to become a leader.

Omada is scaling fast — new cities, new teams, new markets. We need people who can sell and build. Senior Partners step into team lead, city manager, and regional director roles as we grow. You'll recruit, coach, and develop the next generation of reps under you. The playbook you help write today becomes the system hundreds of people run tomorrow.

This is how careers get built — not by waiting for a promotion cycle, but by being early at a company that's moving so fast the opportunities can't keep up with the growth.

A year from now, you're not just a top earner. You're running a team, shaping a region, and sitting on a skillset in AI sales that almost nobody else on the market has.

What We're Looking For

You've done some version of this before — B2B, D2D, field sales, account management — and you were good at it. Beyond that, we want people who are wired to lead. You don't wait to be told what to do. You see a problem and you fix it. You see a newer rep struggling and you pull them aside. That instinct matters more to us than any resume line.

Specifically: proven sales experience with a track record of hitting targets, natural ability to connect with people and build trust fast, comfort with autonomy (nobody's micromanaging you), excitement about AI and what it means for small business, and the kind of drive that doesn't need a manager to stay lit.

Where This Goes

$100K+ in year one is realistic for strong performers — and that number grows as you move into leadership and build your team. We promote from within. Period. The people who show up now, execute, and raise the bar around them are the ones who'll be running regions six months from now.

Omada is backed by HubSpot Ventures, Crosslink Capital, and Ascend. We're one of the fastest-growing AI companies in the country. And we're just getting started.

If you've been waiting for the right thing to go all-in on, this is it.

We're hiring in select cities and looking for people ready to start immediately.

Equal opportunity employer. 1099 independent contractor position.