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Flight Instructor Jobs in Boston, MA (NOW HIRING)

Unifi

Airport Wheelchair Agent - BOS

Boston, MA · On-site

Flight Privileges: Offered after 30 days for employees and eligible family members! * Weekly pay for hourly employees (could change it specific to the state e.g. CA) * Full time starts at 30 hours ...

Swissport International AG

Bagroom Agent

Boston, MA · On-site

$20/hr

Are you ready to take flight in a dynamic and fast-paced aviation industry? As a global leader in aviation services, Swissport provides Ground Handling, Cargo Handling, and Passenger Services to over ...

Swissport International AG

Ramp Agent

Boston, MA · On-site

$20/hr

Are you ready to take flight in a dynamic and fast-paced aviation industry? As a global leader in aviation services, Swissport provides Ground Handling, Cargo Handling, and Passenger Services to over ...

Swissport International AG

Ramp Lead Agent

Boston, MA

$23/hr

Are you ready to take flight in a dynamic and fast-paced aviation industry? As a global leader in aviation services, Swissport provides Ground Handling, Cargo Handling, and Passenger Services to over ...

Swissport International AG

Bagroom Agent

Boston, MA

$20/hr

Are you ready to take flight in a dynamic and fast-paced aviation industry? As a global leader in aviation services, Swissport provides Ground Handling, Cargo Handling, and Passenger Services to over ...

Swissport International AG

Ramp Agent

Boston, MA

$20/hr

Are you ready to take flight in a dynamic and fast-paced aviation industry? As a global leader in aviation services, Swissport provides Ground Handling, Cargo Handling, and Passenger Services to over ...

Swissport International AG

BOS Ramp Lead

Boston, MA

$23.80/hr

Overview: Are you ready to take flight in a dynamic and fast-paced aviation industry? As a global leader in aviation services, Swissport provides Ground Handling, Cargo Handling, and Passenger ...

Swissport International AG

Ramp Lead Agent

Boston, MA · On-site

$23.80/hr

Are you ready to take flight in a dynamic and fast-paced aviation industry? As a global leader in aviation services, Swissport provides Ground Handling, Cargo Handling, and Passenger Services to over ...

G2 Secure Staff

Baggage Service Agent

Boston, MA · On-site

$16.75 - $20.75/hr

Log each flight as bags are delivered to the claim area. Updates records with later arriving bag information. 2. Monitor the delivery of baggage and handle irregularities associated with the internal ...

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All JobsFlight Instructor JobsFlight Instructor Jobs in Boston, MA

Flight Instructor information

See Boston, MA salary details

$27.2K

$102.8K

$158.1K

How much do flight instructor jobs pay per year?

As of Jun 9, 2026, the average yearly pay for flight instructor in Boston, MA is $102,789.00, according to ZipRecruiter salary data. Most workers in this role earn between $75,000.00 and $121,700.00 per year, depending on experience, location, and employer.

What is the difference between Flight Instructor vs Pilot?

AspectFlight InstructorPilot
Required CertificationsCertified Flight Instructor (CFI) certificateCommercial Pilot License (CPL) or Airline Transport Pilot (ATP) license
Work EnvironmentFlight schools, training aircraft, instructional settingsAirlines, charter companies, cargo, private flights
Employer & Industry UsageFlight training academies, flight schoolsAirlines, charter services, corporate aviation

While both Flight Instructors and Pilots operate aircraft, Flight Instructors focus on training and certifying new pilots, requiring specific instructional certifications. Pilots typically operate aircraft for transportation or commercial purposes, holding higher-level licenses. The roles often overlap in aircraft operation but differ mainly in purpose and certification requirements.

What are the key skills and qualifications needed to thrive as a Flight Instructor, and why are they important?

To thrive as a Flight Instructor, you need comprehensive aeronautical knowledge, flight proficiency, and a Certified Flight Instructor (CFI) certificate. Familiarity with flight simulators, aviation weather systems, and logbook management software is commonly required. Strong communication, patience, and the ability to adapt teaching methods to different learning styles are crucial soft skills. These capabilities ensure effective and safe pilot training, fostering student confidence and aviation safety standards.

What are Flight Instructors?

Flight Instructors are certified pilots who teach student pilots how to fly aircraft safely and efficiently. They provide both ground instruction and in-flight training, covering topics such as aviation regulations, aircraft operation, navigation, and emergency procedures. Flight Instructors play a crucial role in helping students gain the skills and experience needed to earn pilot licenses and ratings. They are responsible for ensuring that students understand safety protocols and develop the confidence to operate aircraft independently.

What Is a Flight Instructor?

A Flight Instructor teaches students to fly an aircraft utilizing in-class instruction, a flight simulator, and through test airplane flights. Flight Instructors train students on the physics of aerodynamics, how to manage the navigation and emergency systems, and provide pre- and post-flight checklists. The training process also covers radio procedures and includes practice flights. Flight Instructors are certified pilots themselves, often with hundreds or thousands of hours of flight time, and must remain current on all training and requirements.

What are some common challenges Flight Instructors face when working with student pilots, and how can they address them?

Flight Instructors often encounter students with varying learning styles and confidence levels, which can make it challenging to tailor lessons effectively. Weather conditions and scheduling constraints can also disrupt training plans, requiring flexibility and adaptability. To address these challenges, instructors regularly assess each student's progress, adapt their teaching techniques, and maintain clear communication to ensure safety and comprehension. Building rapport and fostering a supportive learning environment helps students overcome anxiety and develop their skills more effectively.
More about Flight Instructor jobs
What are the most commonly searched types of Flight Instructor jobs in Boston, MA? The most popular types of Flight Instructor jobs in Boston, MA are:
What are popular job titles related to Flight Instructor jobs in Boston, MA? For Flight Instructor jobs in Boston, MA, the most frequently searched job titles are:
What job categories do people searching Flight Instructor jobs in Boston, MA look for? The top searched job categories for Flight Instructor jobs in Boston, MA are:
What cities near Boston, MA are hiring for Flight Instructor jobs? Cities near Boston, MA with the most Flight Instructor job openings:
Flight Instructor jobs near you
Infographic showing various Flight Instructor job openings in Boston, MA as of June 2026, with employment types broken down into 57% Full Time, and 43% Part Time. Highlights an 93% In-person, and 7% Remote job distribution, with an average salary of $102,789 per year, or $49.4 per hour.

Challenger 604 Pilot in Command (PIC)

Waltzing Matilda Aviation, LLC

Bedford, MA • On-site

Other

Retirement

This job post has expired today. Applications are no longer accepted.

Job description

Challenger 604 PIC
Reports To: Chief Pilot
Direct Reports: None
Base: Hanscom AFB (Bedford, MA)
Position Summary
Waltzing Matilda Aviation (WMA) is seeking a Full-Time PIC for Challenger 604 operating under FAR Part 135. Captain will be responsible for aircraft, and other duties as assigned in regard to safe operation of aircraft.
General Requirements
  • CL-604 Type Rating
  • At least 23 years of age
  • High school graduate or GED
  • FAA Airline Transport Pilot Multi-Engine Land Rating (ATP)
  • Current FAA First Class Medical Certificate
  • FCC Radiotelephone Operator's Permit
  • Must pass a 10-year background check and FAA Drug and Alcohol Program testing
  • Must have legal authorization to work in the United States and travel in/out of the United States without restriction
  • Part 135 experience
  • Ability to lift items weighing up to 50 pounds

Flight Time Requirements
  • Minimum of 2500 hours of total documented flight time
  • Minimum 500 hours of turbine time
  • Minimum 100 hours of turbine PIC time
  • Current instrument proficiency check, line check, and route check
  • When evaluating the flight time of applicants meeting the basic qualifications, consideration will be given to, among other things, quality, quantity, recency, and verifiability of training; the complexity of aircraft flown; types of flight operations; and hours flown as PIC in turbine-powered aircraft.

Preferred
  • College Degree

Benefits
  • 401k with company match
  • Benefits Eligible Role/Disability
  • Loss of License (fully covered by employer)
  • Minimum monthly hard days off
  • Company AMEX for all business expenses
  • Great Quality of Life

Compensation
Compensation is competitive with similar operators and equipment types and will be commensurate with the applicant's experience.
Equal Opportunity
WMA is committed to providing equal employment opportunities to all qualified individuals without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, gender identity, genetic information, or any other protected characteristic as outlined by applicable laws. We believe in creating an inclusive and diverse work environment that values and respects the unique contributions of each team member.
We ensure that all employment decisions, including but not limited to recruitment, hiring, training, promotions, compensation, benefits, and terminations, are based on merit, qualifications, and job-related factors. We strive to foster an environment free from discrimination, harassment, and retaliation, and we encourage open dialogue and constructive communication among our employees.
Furthermore, we are committed to providing reasonable accommodations to individuals with disabilities throughout the recruitment and employment process. If you require any accommodations, please inform our Human Resources department, and we will work with you to meet your needs.
About Us
Waltzing Matilda Aviation LLC (WMA) brings together a group of professionals who are passionate about flying, many with over 20 years of aviation experience. WMA is an FAA-licensed Part 135 private jet charter operator. We began private (FAA Part 91) operations in June 2008 and have operated thousands of hours of safe and reliable flying since commencing operations out of the Boston area. We own and operate both our own aircraft as well as managed aircraft. We believe in utilizing the latest technology to ensure the safest operations.
While practicing "Safety Always" in every aspect of job performance and aircraft operations, WMA pilots inspire air travel by keeping our promises to guests and team members and building customer loyalty to our respective brands. Our pilots are responsible for the safe, efficient, reliable, and effective operation of WMA aircraft while always meeting all regulatory requirements and executing company standard operating procedures. WMA Pilots lead by living our values of Safety, Convenient Service, and Reliability.
Come take off with us!
https://wmaviation.com/

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