Night Dispatcher - Intermodal Trucking

JDSB Trucking is a growing 25-truck intermodal drayage carrier serving the Chicago rail ramps. We're hiring a Night Dispatcher to keep freight moving after the day shift hands off — managing drivers, protecting appointments, and setting the next morning up for success. Schedule: Monday–Friday, 5:00 PM – 1:00 AM. Fully on-site at our office near Midway (47th & Laramie area). Compensation: $50,000/year base salary plus up to $8,000/year in performance bonuses — $58,000 total earning potential. Bonuses are paid monthly (up to $650/month) after your first 90 days, tied to clear, measurable goals: next-day pre-planning, same-night ingate and TMS data entry, appointment integrity, and clean morning handoffs. Hit the full bonus consistently and earn. What you'll do: Dispatch and track drivers on evening and overnight container moves Monitor loads in our TMS and GPS platform (Samsara) and update customers proactively Manage rail ramp appointments, ingates/outgates, and last free day deadlines Enter ingate tickets and terminal paperwork into the TMS the same night — no backlog for the morning team Perform nightly TMS cleanup: close out completed moves, correct load statuses, attach documents, and fix data entry errors from the day Pre-plan the next day's loads so the morning team hits the ground running Communicate with drivers via phone and SMS; document everything accurately Flag and escalate problems (equipment issues, missed appointments, detention) before they become expensive What we're looking for: 1+ years of dispatch experience — intermodal/drayage strongly preferred Accurate, fast data entry — clean records are half this job Someone who communicates early and often; no surprises at 7 AM Comfortable working independently — you're the point person on this shift Detail-oriented with load notes, appointment times, and container/chassis numbers Basic computer proficiency; experience with any TMS is a plus Why JDSB: Earn your bonus every month — clear goals, scored transparently, paid the following payroll Stable, established carrier with steady rail freight — not feast-or-famine spot work Small office team where your work is visible and valued Paid time off compliant with Chicago's Paid Leave Ordinance Room to grow as we scale