Account Executive, SMB​/Medium Business

About Toro TMS

Toro TMS is a growth‑stage startup building the modern operating system for trucking. Our focus is squarely on developing best‑in‑class, end‑to‑end transportation management software for bulk commodity haulers. We are a Series B company with a collaborative, high‑energy team of startup veterans.

We are looking for a motivated and results‑driven SMB Account Executive to join our growing sales team in Chicago. In this role, you will own the full sales cycle for small and medium‑sized trucking businesses, building a pipeline from the ground up and helping prospects understand how Toro TMS can transform their operations. This is a high‑velocity, high‑learning role ideal for a seller who is hungry to grow.

• Own the full sales cycle from prospecting and outreach through discovery, demo, and close
• Build and manage a pipeline of qualified SMB opportunities
• Conduct discovery calls and tailored product demonstrations
• Accurately maintain records in the CRM and deliver reliable forecasts
• Consistently meet or exceed monthly and quarterly quota

• 1-2 years of experience in a quota‑carrying sales role
• Track record of meeting or exceeding sales targets
• Excellent communication, presentation, and negotiation skills
• Ability to explain technical products clearly to non‑technical audiences
• Self‑starter who thrives in a fast‑paced, high‑growth environment
• Comfortable with strategic outbound prospecting

• Competitive base salary with uncapped commission structure
• Comprehensive medical, dental, and vision coverage
• 401(k) managed by Empower
• Unlimited PTO
• Significant career growth opportunity at a rapidly scaling startup
• Collaborative, high‑energy culture with a team of startup veterans

Compensation: $100,000 - $150,000 On Target Earnings

Toro TMS is an Equal Opportunity Employer. Toro TMS provides equal employment opportunities to all employees and applicants without regard to race, color, gender (including pregnancy), religion, national origin, ancestry, disability, age, sexual orientation, gender identity or expression, marital status, language, ancestry, genetic information, veteran and/or military status or any other group status protected by federal or local law. If you require reasonable accommodation for the application and/or interview process, please notify a representative of the Human Resources Department.