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Territory Partner (Field Sales)

Omada.ai -
Chicago, IL

Quick Apply

Job Details

Contract
$50,000 - $100,000 a year
10 days ago

Qualifications

Deal closing
Objection handling (sales technique)
Networking through cold outreach
Initial Contact (sales skills)
Prospecting
Canvassing for sales campaigns
Client acquisition
Door-to-door
Sales pipeline management
Closing sales leads

Full Job Description

The Role

Omada AI is the AI marketing platform built for small businesses — and we grow the old-fashioned way: in person, face to face, business by business. Territory Partners are the front line of that motion.

This is a true field sales role. You'll walk into local businesses, pitch owners directly, and get them live on Omada the same day. You find your own prospects, build your own pipeline, and close your own deals. There's no cold-call center behind you and no calendar of pre-booked meetings waiting when you log in — the TPs who win here are the ones who don't need one.

If you've done outside sales before and you know the feeling of turning an empty morning into three signed customers by dinner, keep reading.

What You'll Do

Prospect your territory relentlessly. Identify, approach, and pitch local SMBs — walk-ins, door pulls, referrals, local networking, whatever works. You own your pipeline end to end.
Sell in person. Pitch business owners face to face and get them started in a live free trial on the spot — we don't do demos or demo accounts. You build their system on their real business, with their real content, in front of them.
Run the full sales cycle. From first conversation through trial activation to paid conversion, the deal is yours.
Master the product fast. Omada is straightforward to learn and pitch — most reps are confidently selling within their first day or two. The hard part isn't the product; it's the hustle. That's why we hire for the hustle.
Report and improve daily. Track your activity, present your accounts in team reviews, and sharpen your close rate week over week.

How We Set You Up to Win

Two-week apprenticeship. You start paired with a veteran Territory Partner: shadow their pitches, then prospect together, then close your own deals with their help (with commission split during the ramp). No classroom fluff — you learn this job by doing this job next to someone who's great at it.
Proving Ground. Our performance-gated ramp structure rewards producers quickly. Hit your numbers and your earnings and territory opportunities grow with you.
A real career ladder. TP Vanguard City Captain State Director Regional Director Country Manager. We promote from the field, full stop.
A product that sells. SMB owners need marketing help, most can't afford an agency, and Omada does the work of one for a fraction of the price. When you get in front of the right owner, this sells.

Who We're Looking For

Required:

Proven field / outside sales experience — you've sold face to face before (D2D, B2B field, territory sales, retail energy/telecom/payments, or similar) and you have the numbers to show for it
Demonstrated self-prospecting ability — you've built your own pipeline from zero and you're comfortable walking into a business cold
Closer's mentality — you ask for the business, handle objections in the moment, and don't leave without a next step
Self-managed and disciplined — you run your day like a business owner, because as a 1099 contractor, you are one
Reliable transportation and the ability to work your territory in person daily

You'll thrive here if:

You'd rather be paid for what you produce than for showing up
You like small business owners and can talk to a plumber, a salon owner, and a realtor in the same afternoon
You're energized (not intimidated) by rejection volume
You want a shot at building and leading a market, not just working one

This is not for you if:

You're looking for a role where meetings are booked for you
You need warm leads handed over to get going
You've only sold over the phone or by email and aren't sure about face-to-face

Compensation

Commission-based with performance-gated ramp compensation through our Proving Ground structure. Top producers earn well above typical field sales roles — your income is a direct function of your production. Full details shared during the interview process.

About Omada AI

Omada AI is a Seattle-headquartered AI marketing platform for small businesses, backed by HubSpot Ventures and Crosslink Capital. We're growing fast across the US and promoting our field leaders as we go.

Ready to own a territory? Apply now — our hiring process moves quickly, including a short async video interview and a conversation with a field leader in your region.

Compensation Range: $50K - $100K

Quick Apply

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