Top Tech Jobs & Startup Jobs in Chicago, IL

Handle warm demo appointments delivered by Territory Development Partners, build rapport with small-business owners, overcome objections, close sales on the call (including collecting payment), meet weekly close targets in a high-velocity transactional motion, and help refine the sales playbook. Start on a 30-day contract with conversion to a W-2 Account Executive for reps who hit targets.

Represent Omada.ai in a territory to identify and engage local small businesses, start conversations (in person or by phone), qualify leads using the Route Planner, and book demo appointments. Compensation is commission-based per qualified appointment and closed sale. Role is remote, 1099, and company provides training.

Run warm, qualified demo appointments provided by Territory Development Partners and close sales on the call, including collecting payment. Hit weekly close targets in a high-velocity transactional motion, help refine the sales playbook, start on a 30-day contract (1099) and convert to a W-2 Account Executive if targets are met. Remote, U.S.-based role focused on SMBs.

Represent Omada.ai to local small businesses, identify and qualify leads using a route planner, start conversations in person or by phone, book demo appointments, and earn commissions for shown appointments and closed deals. Opportunity to advance into closing roles.