R44 CFI/CFII/Tour Pilot Massachusetts

R44 CFI/CFII/Tour Pilot Massachusetts

CFI / CFII Flight Instructor, Tour & Charter Pilot R44/Bell 206

Blue Hill Helicopters Norwood, MA (Boston Area)

Blue Hill Helicopters is a charter, flight school, and helicopter tour company based just outside of Boston at Norwood Memorial Airport. Over the years, we have grown significantly expanding our fleet and operations from a dedicated flight school into a diversified helicopter operation offering training, tours, and charter services.

In addition to structured flight training, our operations include introductory flights, scenic helicopter tours, Santa Drops, golf ball drops, photo flights, and a variety of custom aviation projects. This diversity provides our pilots with well-rounded, real-world flying experience beyond traditional instruction. A rare opportunity to get some excellent diverse experience.

We are owned and operated by active career pilots and built on the values of safety, mentorship, integrity, and continuous improvement. We are a small, highly effective, and forward-thinking team that values professionalism, teamwork, and long-term career development.

Who We're Looking For

We are looking for the right personality and mindset above all else.

The ideal candidate is an A-player who works exceptionally well in a team environment, takes ownership, and actively helps uplift the entire team. A customer service mindset is a must, as this role involves regular interaction with students, guests, and high-end clients.

If you are professional, adaptable, safety-focused, and genuinely enjoy working with people while flying, you will thrive at Blue Hill Helicopters.

Why Blue Hill Helicopters?

• Charter, flight training, and helicopter tour operations under one roof
• Small, highly effective, and collaborative team culture
• Owned and operated by active career pilots who understand the industry
• Operations in busy Class D and Boston Class B airspace
• Real-world experience flying structured helicopter routes and complex airspace
• Modern, well-maintained fleet with glass cockpits
• Strong mentorship, standardization, and safety culture
• Clear and realistic career progression beyond instructing

Fleet & Progression

• You will start flying the Robinson R44
• Structured progression into the Bell 206 Jet Ranger as experience and performance milestones are met
• Opportunities to fly under Part 135 charter operations as qualifications, experience, and company needs align

Career Pathways

Due to our strong reputation, high operational standards, and the extensive industry network of our ownership and management team, Blue Hill Helicopters has naturally established meaningful career pathways for both students and instructors.

We offer clearly defined pathway programs for team members as they prepare for their next stage of career progression, including:

• Long-term advancement within Blue Hill Helicopters as our fleet and operations continue to grow
• Tours and Charters opportunities in New York City
• Offshore, housing and IFR in Rhode Island
• HEMS VFR/IFR programs in Boston and across the country
• ENG opportunities in Boston, New York City, and across the country

Responsibilities

• Conduct flight training in accordance with FARs and BHH syllabi
• Lead introductory flights, scenic tours, and commercial operations
• Prepare students for solo flight, checkrides, and certification milestones Maintain accurate student and flight records
• Operate safely and professionally in complex airspace
• Participate in ongoing standardization, training, and evaluation
• Promote and uphold a strong safety culture
• Represent Blue Hill Helicopters with professionalism, enthusiasm, and excellent customer service

Minimum Requirements

• FAA CFI Helicopter
• Instrument Rating Helicopter
• FAA Class II Medical Certificate
• R44 experience
• Minimum 200 rotorcraft hours
• Strong communication and interpersonal skills
• Authorized to work in the United States

Preferred Qualifications

• FAA CFII Helicopter
• SFAR 73 CFI endorsement
• Robinson Safety Course completed or willing to complete
• +25 hours R44 experience
• Experience operating in Class B or other complex airspace
• Background in customer service or client-facing roles
• Excellent communication and interpersonal skills
• Strong organizational habits and ability to work in a team setting

Join Us

Blue Hill Helicopters is more than a flight school it's a launching platform for professional helicopter pilots. If you're looking to grow with a company that is expanding its fleet, operations, and opportunities, we'd love to connect.

To Apply

Send your resume and cover letter to View email address on click.appcast.io

Subject line: CFI / CFII Application [Your Name]