Assistant Director of Operations
Sky Travel Solutions | Kissimmee & Ocoee, FL (Hybrid) | Full-Time, Salaried

Position Summary

Sky Travel Solutions is seeking an experienced and highly qualified Assistant Director of Operations to help lead the day-to-day flight operations of its FAA Part 135 and San Marino charter operations. The Assistant Director of Operations will exercise operational control over company flights, oversee crew scheduling and aircraft availability, and ensure that operations are conducted safely, efficiently and in accordance with applicable Federal Aviation Regulations, San Marino Civil Aviation Authority (CAA) requirements, Operations Specifications, and company manuals and procedures.

The Assistant Director of Operations serves as a key member of Sky Travel’s management team and works closely with the Director of Operations, the Chief Pilot, the Director of Maintenance, the Director of Safety & Compliance and executive leadership to support safe, compliant and on-time operations as the company grows its fleet and expands its international operations. This is a hands-on leadership role with clear growth into senior operations management.

Key Responsibilities

Operational Control

• Exercise operational control over Part 135 flights in accordance with the company’s Operations Specifications and General Operations Manual.

• Oversee flight release, flight locating and flight following, and ensure each flight is properly planned, crewed and documented.

• Make go/no-go decisions in coordination with the Pilot in Command, considering weather, aircraft status, crew qualifications and duty limitations.

• Ensure flight and duty time, rest requirements and crew qualifications comply with 14 CFR Part 135 Subpart F.

• Serve as the operational point of contact for irregular operations, diversions, delays and aircraft-on-ground (AOG) situations.

Crew Scheduling & Fleet Planning

• Oversee crew scheduling to meet charter demand, including assignments, reserve coverage and planning of pilot days off.

• Coordinate aircraft availability with Maintenance, including scheduled inspections, MEL items and return-to-service.

• Plan crew and fleet coverage for peak periods and holidays, and identify staffing needs as the fleet grows.

• Maintain accurate schedules, trip records and crew data in the company’s flight operations software (JetInsight).

Regulatory Compliance & Manuals

• Ensure compliance with applicable FAA regulations (including Parts 91, 119, 120 and 135), Operations Specifications and San Marino CAA requirements.

• Maintain and update the General Operations Manual and related operational procedures, and coordinate revisions with the FAA as required.

• Prepare for and support FAA and San Marino CAA inspections, surveillance and audits, and track findings to closure.

• Support international operations, including required authorizations, documentation and procedures.

• Monitor regulatory changes affecting Part 135 and international operations, and update company procedures accordingly.

Crew Qualifications, Training & Records

• Monitor crewmember qualifications, checkrides, training currency and medical certificates, and ensure no crewmember is scheduled outside of currency.

• Coordinate with the Chief Pilot on initial, recurrent and upgrade training and on line checks.

• Ensure pilot records, including the Pilot Records Database (PRD), are reviewed and complete before a pilot performs duties.

• Work with Human Resources and the Director of Safety & Compliance on pre-employment requirements, including drug and alcohol testing and background checks.

Safety & Leadership

• Support the company’s Safety Management System (SMS), including hazard reporting, risk assessments and corrective actions.

• Lead, mentor and hold flight operations staff and crewmembers accountable to company standards.

• Promote a professional, safety-first culture and communicate operational information clearly to pilots, maintenance personnel and staff.

• Drive process improvements in dispatch, scheduling and operational efficiency.

• Work closely with the Director of Operations to support day-to-day operational decisions, and act on their behalf when required.

Qualifications

Required

• FAA Airline Transport Pilot (ATP) certificate.

• At least 3 years of supervisory or managerial experience within the last 6 years in a position that exercised operational control over Part 135 or Part 121 operations, or at least 3 years of experience as Pilot in Command under Part 135 or Part 121 within the last 6 years.

• Thorough working knowledge of 14 CFR Parts 91, 119, 120 and 135, Operations Specifications and FAA oversight processes.

• Experience with crew scheduling and flight operations software (such as JetInsight or similar).

• Proven leadership skills and the ability to make sound decisions under pressure.

• Excellent written and verbal communication skills.

• Ability to manage multiple priorities and time-sensitive operational issues simultaneously.

• Ability to handle confidential information with discretion and exercise sound judgment in a safety-sensitive, highly regulated environment.

Preferred

• Previous experience as Director of Operations, Assistant Director of Operations, Chief Pilot or a comparable role.

• Type rating in the Hawker 400XP or Cessna Citation Excel (560XL).

• Experience with San Marino CAA or other foreign civil aviation authority requirements.

• International operations experience.

• FAA Aircraft Dispatcher certificate.

• Experience supporting business jet and private charter operations, or a growing multi-aircraft operation.

Schedule & Work Environment

• Full-time position working between the Kissimmee, FL and Ocoee, FL offices on a hybrid schedule.

• Schedule flexibility is required to support FAA Part 135 and San Marino charter operations, including evenings, weekends and holidays, and availability to respond to operational issues.

• Work is performed in office, hangar and ramp environments.

• Occasional travel, including international travel, may be required.

• Must be able to work safely around aircraft, hangar environments and active ramp areas.

Benefits

Competitive benefits package offered to eligible full-time employees. Additional details will be provided during the hiring process.

Sky Travel Solutions is an equal opportunity employer.

Benefits:

• 401(k)

• Dental insurance

• Health insurance

• Life insurance

• Paid time off

• Vision insurance

Application Question(s):

• Do you hold a current FAA Airline Transport Pilot (ATP) certificate?

• In the last 6 years, do you have at least 3 years of experience exercising operational control over Part 135 or Part 121 operations, or as a Pilot in Command under Part 135 or Part 121?

• Do you have working knowledge of 14 CFR Parts 91, 119, 120 and 135 and Operations Specifications?

• Are you available for evenings, weekends and holidays to support flight operations?