About the role
JDSB is seeking an experienced Dispatcher who can step in and run dispatch from day one. You'll coordinate our intermodal drayage fleet across Chicago's rail terminals — directing drivers, managing containers, protecting per-diem exposure, and keeping customers covered. We're looking for someone who already knows freight, moves fast, and wants a seat where performance is rewarded and there's real room to move up.
About JDSB
We started with one truck. We're 25 deep now and just getting started, building the most technologically advanced drayage operation in Chicago. Our mission is simple: move Chicago's freight better, faster, and smarter than anyone else. We're direct, we move fast, we promote from within, and we reward people who produce.
WHAT IT TAKES HERE
HUNGRY — A healthy sense of competition is a must. We reward people who produce and who chase every opportunity to grow.
COACHABLE — You know freight, but every shop runs different. Bring your experience and adapt it to how we win here.
DRIVEN — Containers don't wait, rails don't care, the phone doesn't stop. We want people who run toward problems instead of away from them.
WHAT'S IN IT FOR YOU
- $55,000–$65,000 base salary, based on experience
- Monthly performance bonus up to ~$8,000/year — the better you run your trucks, the bigger your check
- Performance review at 6 months
- A real path up: strong performers move up to Operations Coordinator. We promote from within, not from outside.
WHAT YOU'LL DO
- Run dispatch from day one — coordinate truck and container moves across Chicago's rail terminals
- Direct drivers throughout the day and keep every load on schedule
- Stay ahead of appointments, last-free-days, and per-diem/detention exposure
- Communicate proactively and professionally with customers and operations
- Solve problems and handle escalations independently
- Identify street turns, empty efficiencies, and cost-saving moves
- Keep all moves and container status accurate and current in our TMS
WHAT YOU NEED
- 1–2+ years of dispatch, brokerage, or transportation/logistics experience
- Drayage, intermodal, or Chicago rail experience strongly preferred
- Working knowledge of TMS, appointment scheduling, per diem/detention, and chassis/equipment
- Strong written and verbal communication
- Calm and decisive under pressure
- Organized, detail-oriented, competitive, and coachable
- Elite work ethic — this is 100% in-office
BENEFITS & PERKS
- Paid time off and 6 paid holidays
- Monthly performance bonus on top of base
- Genuine advancement in a fast-growing company — we promote from within
- The best tools in the market: real-time GPS, modern TMS, live yard visibility
WHY JDSB
- We're building something — a one-truck start grown into a 25-truck operation, with a lot more ahead
- Direct, no-nonsense culture where hard work gets noticed and rewarded
- This is a career, not a dead-end seat — the people who help build this company grow with it
ADDITIONAL INFO
- 100% in-office at our Chicago Yard — 5240 W 47th St, Chicago, IL 60638
- Drayage moves early and breaks late. This is not a 9-to-5.
- A brief cover note is highly recommended — tell us why you're a fit.
- Employment includes signing our standard confidentiality agreement.
EQUAL OPPORTUNITY STATEMENT
JDSB Trucking, LLC is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, marital status, disability, or any other status protected under applicable law.
Pay: $55,000.00 - $65,000.00 per year
Benefits:
- Paid time off
- Vision insurance
Work Location: In person
