---
title: Assistant Chief Pilot Northeast at Tradewind
description: Tradewind is hiring for the Assistant Chief Pilot Northeast role in West Harrison,
  NY. See the full description and apply.
type: job
url: https://www.foundrole.com/jobs/assistant-chief-pilot-at-tradewind-01a13b21-0879-731a-8916-505cce06cdfa
date: 2026-11-15T17:42:40Z
og_description: Join Tradewind as Assistant Chief Pilot Northeast in West Harrison, NY. Pays $110K–$180K
  per year. Full-time, on-site role.
og_image: https://www.foundrole.com/og/u1414e.png
breadcrumbs:
  - label: Home
    url: https://www.foundrole.com/
  - label: Search
    url: https://www.foundrole.com/jobs
---

| | |
|---|---|
| **Company** | Tradewind |
| **Location** | West Harrison, NY |
| **Salary** | $110K/yr - $180K/yr |
| **Type** | Full Time |
| **Posted** | Oct 14, 2026 |

## Is this job real?

**Ghost job check:** A- · Low risk. Probably a real opening.

## Visa sponsorship

- **H-1B:** No H-1B sponsorship on record for Tradewind.
- **E-Verify:** No E-Verify enrollment on record for Tradewind.

## Pay for similar jobs

Most similar jobs pay $103,000 – $275,000 a year (median $193,000).

## Description

**About Tradewind**

Tradewind Aviation is a leading Part 135 commuter and on-demand private charter operator with operational bases at the Waterbury/Oxford, CT (OXC), Westchester, NY (HPN), Stuart, FL (SUA) and San Juan, PR (SJU) airports. Founded by aviation enthusiasts in 2001 on the premise that all flights deserve the highest quality aircraft, crew, and service, Tradewind provides personal air travel—both private and scheduled service—throughout North America and the Caribbean.

For more details visit www.flytradewind.com

**About the Candidate / Role**

Tradewind Aviation is seeking dedicated and experienced Assistant Chief Pilot to support our Northeast (HPN) operations. This role is designed for a proactive aviation leader who thrives in a dynamic environment and is committed to safety, operational excellence, and pilot support. The Assistant Chief Pilot will work closely with the Chief Pilot and company leadership to support day-to-day flight operations, oversee pilot activity in their assigned region, and ensure compliance with FAA regulations, company policies, and Tradewind’s safety culture. This is primarily an in-office role, with limited flying responsibilities.

**Essential Functions**

**Pilot Support & Coordination**

- Serve as a point of contact for pilots within the region, providing guidance and assistance on operational matters.
- Help identify and elevate operational, performance, or safety concerns to appropriate leadership for review and resolution.
- Support compliance with company procedures, regulatory requirements, and safety standards through regular communication and follow-up.
- Foster positive working relationships with flight crews and promote effective communication between pilots and leadership.
- Assist with pilot engagement initiatives and help maintain a collaborative and professional team environment.

**Operational Support & Compliance**

- Support the Chief Pilot in maintaining compliance with FAA regulations, company manuals, and all operational standards.
- Assist in maintaining operational control and facilitating communication between flight crews, Dispatch, and leadership.
- Monitor crew qualifications, scheduling requirements, and readiness for assigned missions for trip executed in the assigned region.
- Ensure adherence to the General Operations Manual and other company guidance.

**Training & Checking**

- Conduct pilot evaluation, ground and flight training, base-level standardization, and recurrent/proficiency activities as assigned.
- Support the Director of Operations and Director of Training in evaluating and enhancing training programs.
- Maintain knowledge of current aviation regulations, company policy changes, and industry best practices, ensuring timely dissemination of relevant updates to flight crews.

**Administration & Base Management**

- Serve as the primary liaison for region-specific pilot issues, operational needs, and personnel support.
- Assist with performance evaluations, coaching, documentation, and follow-up actions.
- Participate in pilot recruiting, interviewing, and onboarding activities for the assigned region.
- Coordinate initiatives, pilot meetings, and local operational improvements.

**Cross-Functional Collaboration**

- Collaborate closely with the Chief Pilot, SVP of Operations, Director of Operations, Director of Training, and Safety Department to align region activities with company goals.
- Support safety investigations, corrective action plans, and proactive safety initiatives.

**Flying & Operational Duties**

- Perform limited line flying as required, including missions supporting training, checking, and operational continuity.
- Maintain personal qualifications and currency in accordance with company policies and FAA requirements.

**Other Duties**

- Carry out additional assignments as assigned by the Chief Pilot

**Qualifications**

- Commercial or ATP certificate with appropriate ratings for company operations.
- Strong knowledge of FAA Part 135 regulations and operational requirements.
- Previous experience in supervision, or pilot development strongly preferred .
- Excellent communication, interpersonal, and problem-solving skills.
- Ability to work flexibly, support on-call operational needs, and travel occasionally.
- Demonstrated commitment to safety, professionalism, and high operational standards.

**Tradewind Aviation offers a competitive pay and benefits program for full-time team members:**

- Comprehensive health and voluntary insurance plans
- Retirement plan with company match
- Paid time off
- Standby travel on select Tradewind Aviation scheduled flights
- Discounted standby travel benefits on numerous major and regional US and international airlines
- A rewarding career path with opportunities for growth and advancement throughout the organization

Salary Range: $110k-$180k a year
## Skills

- FAA Part 135 Operations
- Onboarding
- Supervision
- Training And Development
- Investigation
- Performance Management
- Problem Solving
- Civil Aviation Regulations
- Interpersonal Skills
- Interviewing Skills
- Corrective And Preventive Action (Capa)
- Human Resources
- Leadership
- FAA Regulations
- On-Call Coverage
- Communication
- Recruitment
- Coaching
- Equities
- Business Continuity
- Regulatory Compliance
## Benefits

- Health Insurance
- Paid Time Off (Pto)
- Other Retirement and Savings

## Related

- [Logistics & Transportation jobs](https://www.foundrole.com/careers/logistics-and-transportation?utm_source=ai_markdown)- [Aviation Operations jobs](https://www.foundrole.com/careers/logistics-and-transportation/aviation-operations?utm_source=ai_markdown)- [Pilot jobs](https://www.foundrole.com/careers/logistics-and-transportation/aviation-operations/pilot?utm_source=ai_markdown)- [Browse all companies](https://www.foundrole.com/companies?utm_source=ai_markdown)

## Related pages

- [New York](https://www.foundrole.com/locations/us/new-york?utm_source=ai_markdown) — 149919 jobs
- [Airlines and Aviation](https://www.foundrole.com/sectors/aerospace-and-defense/airlines-and-aviation?utm_source=ai_markdown) — 6566 jobs

## Browse

- [Companies](https://www.foundrole.com/companies?utm_source=ai_markdown)
- [Jobs by country](https://www.foundrole.com/locations?utm_source=ai_markdown)
- [Jobs in the United States by state and city](https://www.foundrole.com/locations/us?utm_source=ai_markdown)
- [H1B sponsors by location](https://www.foundrole.com/h1b-sponsors?utm_source=ai_markdown)
- [H1B salaries](https://www.foundrole.com/h1b-salaries?utm_source=ai_markdown)
- [Sectors and industries](https://www.foundrole.com/sectors?utm_source=ai_markdown)
- [Jobs by career field](https://www.foundrole.com/careers?utm_source=ai_markdown)
- [Latest jobs](https://www.foundrole.com/jobs/latest?utm_source=ai_markdown)