Class A Driving Instructor

Join a Team That Invests in You

Canandaigua Driving School is growing, and we’re looking for a Class A CDL Driving Instructor to help train the next generation of safe, confident commercial drivers. If you enjoy teaching, mentoring, and making a real impact, this is a rewarding opportunity with excellent pay, stability, and full benefits.

This is a full-time, day-shift position located at our Farmington, NY training facility.

What’s In It for You

• A supportive, team-oriented work environment
• Competitive hourly pay: $26–$27/hr (based on experience)
• Weekly pay
• Comprehensive benefits package including:
  • Medical (Excellus Blue Cross/Blue Shield)
  • Prescription, dental, and vision coverage
  • Wellness program
• 401(k) with up to 4% company match
• Company-paid life insurance
• Paid Time Off + Paid Holidays
• On-site gym + gym membership reimbursement

Who Thrives in This Role

We’re looking for someone who:

• Has previous driving instructor experience
• Communicates clearly—both verbally and non-verbally
• Shows patience and professionalism with new drivers

We also welcome applicants who:

• Have teaching or training experience in any field
• Have no formal training background but maintain an excellent work record and a positive, coachable attitude

What You’ll Do

As a CDL Instructor, you’ll provide hands-on and classroom instruction to help students safely operate Class A and Class B commercial vehicles.

Essential Duties

• Teach core driving skills: turns, curves, backing, intersections, etc.
• Train students on proper safety inspections
• Evaluate student progress and determine readiness for road instruction
• Provide instruction on upgrades, downgrades, starting, and stopping
• Maintain a positive, encouraging learning environment
• Perform additional duties as assigned

Additional Expectations

• Demonstrate patience and professionalism with students of all skill levels
• Communicate effectively with both new and experienced drivers
• Adapt teaching methods to individual learning styles
• Exercise sound judgment and discretion
• Show leadership and a commitment to continuous improvement

(Some requirements are mandated by New York State law.)

Education & Experience

• At least 21 years of age
• High School Diploma or High School Equivalency
• Minimum 2 years of Class A CDL driving experience with an active CDL and no suspensions or revocations in the past 2 years
• Must pass NY DMV written, visual, road sign, and road tests
• Must not have been convicted of a felony or crimes involving violence, dishonesty, deceit, indecency, or degeneracy (per NYS regulations)

Physical Requirements

This role involves outdoor instruction in varying weather conditions. You must be able to:

• Occasionally lift/move up to 50 lbs
• Bend, kneel, or lie down outdoors as needed
• Stand and walk on hard surfaces for most of the shift while observing students

How to Apply

Apply directly through this posting or call us at 585-742-2303.

About Us

Canandaigua Driving School is part of the Leonard’s Express Family of Companies, a family-owned transportation provider headquartered in Farmington, NY with locations nationwide. We deliver dependable, creative, and cost-effective transportation solutions across a wide range of industries.

We offer diverse career opportunities across New York, Delaware, North Carolina, Idaho, and beyond—whether your background is in driving, operations, maintenance, safety, HR, IT, finance, recruiting, or customer service.

Equal Opportunity Employer

All Leonard’s Express companies are equal opportunity employers. We do not discriminate based on race, color, religion, sex, national origin, veteran status, disability, age, sexual orientation, gender identity, or any other characteristic protected by law.

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