Sales Representative (AI)

Location: Chicago, IL, United States — on-site

Salary: Competitive salary plus uncapped commission

Company

Builds AI agents for the American trucking industry to help carriers find loads, negotiate rates, manage documents, and automate dispatch operations.

What you will do

• Run tailored product demos for trucking company owners and dispatchers.
• Manage the full sales pipeline from first contact through signed contract.
• Follow up consistently, handle objections, and move deals toward close.
• Meet monthly revenue targets and maintain accurate CRM records.
• Share market feedback directly with the product team.

Requirements

• At least 2 years of experience in a closing sales role with quota ownership.
• Strong English communication skills, written and spoken, for working with U.S. clients.
• High discipline, consistency, and ability to work without close supervision.
• Comfort with sales targets and rejection.
• Ability to learn products quickly and understand them in depth.

Nice to have

• Experience selling to SMBs or in logistics, trucking, or SaaS.
• Familiarity with U.S. business norms and buyer behavior.
• Experience with outbound-heavy or phone-first sales.

Culture & Benefits

• Direct access to the founding team and short decision-making paths.
• Ownership of individual sales results.
• Compensation tied directly to performance.
• Uncapped commission.