Trading Instructor Jobs in Chicago, IL (NOW HIRING)

Description

About the Role

160 Driving Academy is the largest CDL training school in the country - 14 years strong, 90+ locations across 32 states, training roughly 20,000 students a year with an overall 88% average first-time pass rate. Our instructors are why.As a CDL Class A Instructor Trainer, you teach students from their first pre-trip inspection to the day they pass their CDL exam - in the yard, and behind the wheel.  You will be based at a designated yard, working alongside a team of instructors and a Lead Instructor. From time to time, you may be asked to fill in at other regional yards when coverage is needed. Keeping your yard clean and presentable - light upkeep such as litter pickup, basic painting, and general tidiness - is part of the role. This is local, hands-on work for experienced Class A drivers ready to trade the long-haul life for a role that keeps you home every night and pays you for outcomes that matter.

Our Compensation

• Opportunity for annual merit increases to hourly wage based on business performance.
• Monthly bonus pool payout: When your yard averages an 80% first-time pass rate, every first-time pass adds $100 to a shared pool, split across the team and paid monthly. Full bonus eligibility requires a 4.7/5 average student rating.
• $100 accident-free bonus for top 15 yards. Additional paid hours for placement fairs and truck care during scheduled downtime.

Our Schedule

• Monday through Friday, 7:00 AM to 3:30 PM or 8:00 AM - 4:30PM for most yards.
• Higher volume yards sometimes run seven days a week, ten hours per day - opening alternative shifts including some four-day work weeks with three days off.
• Occasional fill in at another regional yard. There is a possibility to stay over in a hotel.  Per diem paid, and mileage is paid if you are using your own vehicle.
• Students depend on their instructors being present. Reliable, on-time attendance is core to the role.

What You Will Do At 160 Driving Academy

• Teach Class A driving skills using hands-on training in outdoor yards on automatic and manual transmissions.
• Guide students step-by-step through pre-trip inspections, yard maneuvers, and on-road driving.
• Prepare students to pass CDL testing standards on the first attempt.
• Track student attendance and progress; provide additional support when needed.
• Maintain accurate training records, evaluations, and documentation.
• Reporting of all incidents and accidents to your lead and corporate in a timely manner.
• Work closely with fellow instructors and your Lead Instructor to deliver a consistent student experience and follow our defined curriculum.
• Help keep the yard and building clean and presentable
• Cover for other instructors at nearby regional yards in certain emergencies.
• 90-day probationary period to ensure adherence to safety, compliance and curriculum.
• Assist with the transfer of trucks to repair operations and neighboring yards for use.
• Student-centric approach to teaching with ability to exhibit patience and professionalism.
• Ability to climb in/out of a tractor cab, sit and stand for extended periods, and demonstrate maneuvers.
• Additional requirements that apply specific to the role may be requested.

Our Benefits

• Medical and dental (shared expense).
• Paid vacation: 1 week to start, 2 weeks after year 1, 3 weeks after year 2.
• 8-hour paid day off for a full year of perfect attendance.
• Paid day off for your birthday after 1 year of service (8 hours floating holiday)
• $3,000 relocation benefit for moving to our locations 100+ miles away.
• $500 referral bonus per instructor hire.
• Branded gear (vests, hats, flashlights, gauges) and access to yard laptops.
• Career path: Yard Instructor ? Assistant Lead Instructor ? Lead Instructor ? Regional Manager.

Why Work At 160 Driving Academy?

We train the people America runs on. With 90+ yards across 32 states and the highest training volume of any CDL school in the country, we're growing where the industry is growing - which means real career paths for our people, not just our students. If you've spent your career behind the wheel and you're ready to use what you've learned to launch other drivers' careers, we want to talk. 160 Drivers Academy appreciates and supports our nations' great veterans who are strongly encouraged to apply. We Are An Equal Opportunity Employer 160 Driving Academy is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran status, disability status, or any other legally protected characteristic.Are you an experienced CDL A Driver looking for a local position where you can use your skills to train the next generation of truck drivers?  At 160 Driving Academy, we are hiring experienced truck drivers who want to become CDL instructors. We provide structured training and support to prepare you for this role.   With 90 locations across 32 states, we offer career stability and relocation opportunities within our network of schools.  

Responsibilities

• Teach students CDL A driving skills through classroom instruction and hands-on training.
• Provide step-by-step guidance in pre-trip inspections, yard maneuvers, and road driving.
• Ensure students understand CDL testing standards and are fully prepared for the exam.
• Promote safety, professionalism, and industry best practices in all training.
• Track student attendance and progress, providing additional support when needed.
• Maintain proper documentation, including student evaluations and training records.
• Work collaboratively with other instructors to provide an effective training experience.

What We Offer

• Local, steady work schedule with no overnight travel.
• Hourly pay based on experience.
• Comprehensive benefits package, including health, dental, vision, PTO, and paid holidays.
• Onboarding and training to help you transition from driver to instructor.
• Career stability and relocation opportunities.
• An opportunity to make a lasting impact by training the next generation of truck drivers.

At 160 Driving Academy, we are committed to helping truck drivers become skilled instructors so they can pass on their knowledge and support new drivers entering the industry.    Apply today to start your career as a CDL A Instructor Trainer. Equal Opportunity Employer Statement160 Driving Academy is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, gender, national origin, age, sexual orientation, gender identity or expression, protected veteran status, disability/handicap status, or any other legally protected characteristic.

Requirements

Our Required Credentials

• High school graduation certificate or equivalent.
• Valid Class A CDL with a minimum of 24 months of verifiable Class A tractor-trailer driving experience.  Exception - The State of Nevada requires 5 years of Class A CDL experience.
• The state where you obtained your driver's license must be the same state where you are applying to work at a 160 Driving Academy location.
• Manual transmission experience - licensed to operate and able to teach manual transmission.
• Motor Vehicle Record (MVR) free of violations.
• Ability to pass DOT physical and DOT-mandated drug and alcohol screening.
• Background check clearance required.
• Strong communication skills with the ability to mentor and coach students.
• Basic computer skills for tracking student progress and scheduling.
• Residence in the state you are applying for, or a confirmed residence secured for relocation.
• Must meet all state requirements for instructor licensing where instructor licensing is required.
• 90-day probationary period at hire.

Preferred Experience

• Four or more years of consistent Class A driving experience.
• Prior experience mentoring, coaching, or training drivers.
• Driver Training Instructor certification (we provide guidance and support to obtain it if your state requires it).