Cessna 208 Caravan Captain – Milwaukee (Overnight Cargo)

Pilot Assessments; Milwaukee (WI); On-site; USD 110,000 - 180,000; Full time

Job summary

Pilot Assessments in Milwaukee seeks a Captain to fly freight on a dedicated route, typically outstationed rather than at a hub, with nightly leg time and a steady weekday rotation. Overnight stays at the hub are provided, and accommodations are arranged to support a regular schedule.

You will operate with a professional team, ensure safe, on-time performance, and communicate clearly to customers, suppliers, and colleagues while maintaining high standards of regulatory compliance.

Qualifications

• Flight time minimums: 1,200 hours total time; 500 hours PIC; 500 hours cross-country; 100 hours night; 75 hours instrument, including 50 hours actual.

Responsibilities

• Serve as Captain on a dedicated freight route, typically domiciled at an outstation rather than the hub.
• Fly freight from the domicile airport to the hub overnight; return freight to the domicile in the morning.
• Overnight at the hub in company-provided accommodations and maintain a consistent weekday rotation.
• Perform quality work within deadlines with or without direct supervision.
• Interact professionally with fellow employees, customers, suppliers, and service agencies.
• Contribute effectively as part of a team while working independently and communicating clearly.

Job description

What you’ll do

• Serve as Captain on a dedicated freight route, typically domiciled at an outstation rather than the hub.
• Fly freight from the domicile airport to the hub overnight; return freight to the domicile in the morning.
• Overnight at the hub in company-provided accommodations and maintain a consistent weekday rotation.
• Perform quality work within deadlines with or without direct supervision.
• Interact professionally with fellow employees, customers, suppliers, and service agencies.
• Contribute effectively as part of a team while working independently and communicating clearly.

What you’ll bring

• Flight time minimums: 1,200 hours total time; 500 hours PIC; 500 hours cross-country; 100 hours night; 75 hours instrument, including 50 hours actual.
• Medical: Current FAA Second Class Medical.
• Currency: IFR currency/proficiency.
• Work authorization: U.S. citizenship or authorization to work in the United States.
• Comfort operating a Monday–Friday/Saturday overnight schedule with hub overnights and daytime at home.

What’s in it for you

• A stable, growth-oriented, and inspiring work environment with opportunities for professional, personal, and financial growth.
• Hub accommodations provided by CSA (hotel or crew apartments) when overnighting.
• Two weeks of paid time off in addition to regular vacation.
• Uniform allowance and company-provided EFB.
• Comprehensive benefits package.
• Predictable weekday schedule that repeats Monday night through Friday or Saturday morning.