Transportation Sales Representative

Circle Logistics, Inc; Chicago (IL); On-site; USD 40,000 - 60,000; Full time

Benefits offered by this job

Paid holidays

Medical, dental, and vision insurance

401(k) plan

Dog‑friendly office

Job summary

Circle Logistics, Inc. in Chicago is looking for Transportation Sales Representatives to drive new business and build customer relationships. This role offers a fast-paced environment where you will actively engage with clients to deliver innovative transportation solutions.

We provide comprehensive training and support, promoting long-term careers in transportation sales. In addition to a competitive salary with uncapped commission, you'll benefit from a collaborative office, casual dress code, and various insurance options.

Qualifications

• Sales, customer service, or logistics experience preferred.
• Strong communication and relationship‑building skills.
• Ability to thrive in a fast‑paced environment.

Responsibilities

• Generate new business opportunities through outbound prospecting.
• Build and maintain customer relationships.
• Serve as the primary point of contact for customer communication.

Skills

Sales experience

Customer service skills

Communication skills

Relationship building

Problem-solving skills

Tools

Google Workspace

Microsoft Excel

TMS and CRM platforms

Job description

At Circle Logistics, our Transportation Sales Representatives play a key role in driving new business, building customer relationships, and delivering innovative transportation solutions in a fast‑paced industry. This is a high‑energy opportunity for motivated individuals who thrive on communication, problem solving, and building long‑term partnerships.

Whether your background is in sales, hospitality, athletics, retail, customer service, or logistics, we provide the training, mentorship, and support needed to help you build a successful long‑term career in transportation sales.

What You'll Do:

• Generate new business opportunities through outbound prospecting, relationship building, and customer outreach
• Build and maintain customer relationships by managing daily transportation needs and communication
• Match customer freight demands with transportation solutions and competitive pricing
• Develop strategies that drive sales growth and strengthen long‑term partnerships
• Serve as the primary point of contact for customer communication, shipment updates, and issue resolution
• Organize and manage daily shipments to support Circle Logistics’ “No‑Fail Service” commitment
• Collaborate with internal teams on pricing strategy, shipment execution, and account implementation
• Stay informed on market trends and transportation solutions to better support customers

What You'll Need:

• Sales, customer service, hospitality, athletics, retail, or logistics experience preferred, but not required
• Strong communication and relationship‑building skills
• Experience with or ability to quickly learn TMS and CRM platforms
• Above‑average proficiency with Google Workspace and Microsoft Excel
• Ability to thrive in a fast‑paced, high‑energy environment and multitask effectively
• Strong time management, organization, and problem‑solving skills
• Competitive mindset with a strong sense of urgency and accountability
• Excellent teamwork and collaboration skills

What We Offer:

• Starting base salary with uncapped commission potential (compensation negotiable based on experience)
• Clear path for advancement within a fast‑growing company that promotes from within
• Hands‑on training, mentorship, and career development
• Collaborative and energetic office environment
• Casual dress code
• Paid holidays and paid time off
• Medical, dental, and vision insurance benefits
• 401(k) plan
• Dog‑friendly office

Ready to launch your career in transportation sales and grow with one of the fastest‑growing logisticscle Logistics can take you.