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Contract Pilot Jobs in Oregon (NOW HIRING)

Anterix

Sales Director - West Coast

Oregon City, OR

Lead the negotiation of complex contracts through various stages, including pilots, Letters of Intent (LOIs), and final contract execution. * Relationship Management: Build multi-level relationships ...

New Narrative

Peer Supervisor

Beaverton, OR · On-site

$62K/yr

The Peer Supervisor will oversee additional pilot programming expansions of the existing contract and ensure all required documentation and invoicing is completed in accordance with contractual ...

Varsity Tutors

FAA Tutor

Eugene, OR · Remote

$18 - $40/hr

... human factors for pilot certification. Ability to explain principles of flight, airspace ... Varsity Tutors does not contract in: Alaska, California, Colorado, Delaware, Hawaii, Maine, New ...

Varsity Tutors

FAA Tutor

Portland, OR · Remote

$18 - $40/hr

... human factors for pilot certification. Ability to explain principles of flight, airspace ... Varsity Tutors does not contract in: Alaska, California, Colorado, Delaware, Hawaii, Maine, New ...

Varsity Tutors

FAA Tutor

OR · Remote

$18 - $40/hr

... human factors for pilot certification. Ability to explain principles of flight, airspace ... Varsity Tutors does not contract in: Alaska, California, Colorado, Delaware, Hawaii, Maine, New ...

Protingent

O&M Digital Project Coordinator

Corvallis, OR · On-site

$40 - $60/hr

Protingent Staffing has an exciting contract O&M Digital Project Coordinator with our client that ... Support implementation planning and pilot-to-scale transition readiness. * Performs other duties as ...

Amerit Fleet Solutions

You will drive the full vendor lifecycle (contract execution, labor rate negotiation, invoice and ... pilot, Claude, Gemini, etc.). Working Conditions * Role will require travel (5-10% as needed ...

Amerit Fleet Solutions

You will drive the full vendor lifecycle (contract execution, labor rate negotiation, invoice and ... pilot, Claude, Gemini, etc.). Working Conditions * Role will require travel (5-10% as needed ...

Aspira Connect

Project Manager

... from contract award or renewal through successful delivery · Partner with Account Management to ... pilots, or special projects · Collaborate with stakeholders to define deliverables, identify ...

United Way of Greater Los Angeles

OR

Pilot AI tools for outcome tracking and reporting under the AI for Internal Efficiency priority ... Confirm Service Providers meet contract reporting requirements, including timely invoices, data ...

Integrated 3D

IT & Automations Manager

Redmond, OR · On-site

$90K - $100K/yr

I3D contracts with CMIT, an outside IT vendor, for IT support. This position is intended to provide ... pilot and roll out approved tools. Help establish and maintain AI usage guidelines, approval ...

Integrated 3D

IT & Automations Manager

Redmond, OR · On-site

$90K - $100K/yr

I3D contracts with CMIT, an outside IT vendor, for IT support. This position is intended to provide ... pilot and roll out approved tools. * Help establish and maintain AI usage guidelines, approval ...

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Showing results 21-40

All JobsContract Pilot JobsContract Pilot Jobs in Oregon

Contract Pilot information

See Oregon salary details

$52.3K

$138.4K

$212.5K

How much do contract pilot jobs pay per year?

As of Aug 12, 2026, the average yearly pay for contract pilot in Oregon is $138,416.00, according to ZipRecruiter salary data. Most workers in this role earn between $105,700.00 and $163,900.00 per year, depending on experience, location, and employer.

What does a contract pilot do?

A contract pilot is an aviation professional who operates helicopters, charter planes, or another aircraft on a per-job basis. As a contract pilot, you work directly with corporate or individual clients to fly an aircraft between locations and transport passengers or cargo. Your contract may be for a single trip or multiple trips. However, you operate as an independent contractor, so you are responsible for maintaining your credentials and insurance. Working as a contract pilot provides you with greater flexibility than being a pilot for an airline or the military.

What are some common challenges faced by contract pilots when adapting to different aircraft and client expectations?

Contract pilots often fly a variety of aircraft types for different clients, which can require quick adaptation to new cockpit layouts, avionics systems, and company-specific procedures. Additionally, each client may have unique operational standards and expectations regarding communication, scheduling, and reporting. Staying organized, maintaining up-to-date certifications, and being proactive in learning new processes are key strategies for overcoming these challenges. Strong interpersonal skills also help contract pilots integrate smoothly with new crews and flight departments.

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

To thrive as a Contract Pilot, you need extensive flight experience, an active commercial or airline transport pilot license (CPL/ATPL), and current medical certification. Familiarity with specific aircraft types, proficiency in using advanced avionics systems, and completion of required type ratings are typically necessary. Strong decision-making, adaptability, and effective communication skills help you manage diverse flying environments and coordinate with clients and crews. These competencies ensure safety, regulatory compliance, and reliable service in varied and dynamic aviation assignments.

What is a contract pilot?

Contract pilots are professional pilots who are hired on a temporary or per-assignment basis, rather than as full-time employees of an airline or company. They typically operate private jets, corporate aircraft, or charter flights for individuals or organizations that need flight services for a limited period. Contract pilots are responsible for pre-flight planning, operating the aircraft safely, ensuring compliance with aviation regulations, and sometimes handling administrative tasks related to each flight. This flexible arrangement allows both pilots and employers to meet their scheduling and operational needs without long-term commitments.

What is the difference between Contract Pilot vs Commercial Pilot?

AspectContract PilotCommercial Pilot
CertificationsCommercial Pilot Certificate, possibly additional type ratingsCommercial Pilot Certificate, multi-engine ratings often required
Work EnvironmentHired on a temporary basis for specific contracts, often freelanceEmployed by airlines, charter companies, or corporate operators
Employer & Industry UsageContract basis across various operators, including private and cargoFull-time or part-time employment within commercial aviation

Contract pilots typically hold a commercial pilot certificate and work on a temporary or project basis, often flying for multiple operators. Commercial pilots are usually employed full-time by airlines or companies, with a focus on scheduled or charter flights. The main difference lies in employment type and job stability, with contract pilots offering flexibility and diverse opportunities, while commercial pilots often have more consistent employment within the commercial aviation industry.

More about Contract Pilot jobs
What are the most commonly searched types of Pilot jobs in Oregon? The most popular types of Pilot jobs in Oregon are:
What are popular job titles related to Contract Pilot jobs in Oregon? For Contract Pilot jobs in Oregon, the most frequently searched job titles are:
What job categories do people searching Contract Pilot jobs in Oregon look for? The top searched job categories for Contract Pilot jobs in Oregon are:
What cities in Oregon are hiring for Contract Pilot jobs? Cities in Oregon with the most Contract Pilot job openings:
Contract Pilot jobs near you
Infographic showing various Contract Pilot job openings in Oregon as of August 2026, with employment types broken down into 85% Full Time, 11% Part Time, 3% Contract, and 1% Nights. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $138,416 per year, or $66.5 per hour.

Systems Engineer - AI Research Systems Support

Aptive

On-site, Remote

Part-time

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

Aptive Environmental rating

5.6

Company rating: 5.6 out of 10

Based on 39 frontline employees who took The Breakroom Quiz

30th of 35 rated pest control companies

Job description

Job Summary

Aptive Resources is seeking a Systems Engineer to support artificial intelligence (AI), research systems, and data modernization initiatives within the Department of Veterans Affairs (VA) Office of Research and Development (ORD). This role supports enterprise AI activities focused on improving research operations, streamlining organizational workflows, supporting strategic AI pilots, and enabling scalable AI capabilities across research, policy, infrastructure, and operational environments.

The Systems Engineer will support development, integration, and optimization of AI-enabled workflows, cloud-based solutions, and research technology initiatives. This role will work closely with project managers, data analysts, operational stakeholders, and technical teams to support rapid testing, workflow improvements, system integrations, and AI-related operational support activities across ORD initiatives.

The ideal candidate will have experience supporting modern data and application environments, technical integrations, cloud-based systems, and AI-enabled workflows in healthcare, research, or enterprise operational environments.

This is a full-time (40 hours/week), 100% remote position. 

It is currently funded through September 29, 2026 under the current contract period of performance, with potential for extension into the next option year based on contract continuation and program needs.

Primary Responsibilities
  • Support development and implementation of AI-enabled operational and research support solutions across ORD initiatives.
  • Assist with integration, optimization, and maintenance of data systems, workflows, and cloud-based platforms supporting AI and analytics activities.
  • Support development and testing of retrieval-augmented generation (RAG) workflows and related AI-enabled tools.
  • Assist with development of simplified workflows, rapid testing approaches, and deployment activities to improve operational efficiency and development speed.
  • Support data ingestion, ETL processes, database integration, and data pipeline activities across enterprise environments.
  • Assist with development and maintenance of integrations supporting research operations, analytics, reporting, and AI-enabled tools.
  • Coordinate with technical and operational stakeholders to support AI pilot initiatives and enterprise operational priorities.
  • Support activities related to centralized AI assets, research infrastructure, and enterprise data environments.
  • Participate in troubleshooting, issue resolution, and continuous improvement activities across technical workstreams.
  • Prepare technical documentation, workflow documentation, and implementation support materials.
Minimum Qualifications
  • Bachelor's degree in information systems, computer science, engineering, data science, healthcare informatics, or a related technical field.
  • 4+ years of experience supporting systems engineering, software integration, cloud solutions, data systems, or technical implementation activities in a complex organization.
  • Experience supporting cloud-based environments, databases, data pipelines, or enterprise data activities.
  • Experience with SQL, Python, ETL processes, APIs, or systems integration activities.
  • Familiarity with AI/ML technologies, large language models (LLMs), or AI-enabled workflow solutions.
  • Experience supporting rapid development, testing, or deployment activities in technical environments.
  • Strong analytical, troubleshooting, and problem-solving skills.
  • Ability to communicate effectively with both technical and non-technical stakeholders.
  • Proficiency with Microsoft Office Suite and collaboration platforms.
  • Ability to work independently in a remote environment while managing multiple priorities.
  • Ability to obtain and maintain a public trust clearance.
  • Legal authorization to work in the United States.
Desired Qualifications
  • Experience supporting federal, VA, healthcare, research, or enterprise AI environments.
  • Experience supporting AI-enabled search, retrieval workflows, or RAG-based solutions.
  • Familiarity with cloud platforms such as Azure or AWS.
  • Experience supporting workflow automation, operational modernization, or technical integration initiatives.
  • Experience supporting REDCap, research databases, or healthcare data environments.
  • Familiarity with data lake, data warehouse, or enterprise analytics environments.
  • Experience working in fast-paced, matrixed environments supporting multiple concurrent technical initiatives.
  • High degree of professionalism, discretion, and mature judgment in handling sensitive information.
About Aptive

Aptive partners with federal agencies to achieve their missions through improved performance, streamlined operations and enhanced service delivery. Based in Alexandria, Virginia, we support more than a dozen agencies including Veterans Affairs, Transportation, Defense, Homeland Security and the National Science Foundation.

We specialize in applying technology, creativity and human-centered services to optimize mission delivery and improve experiences for millions of people who count on government services every day.

Founded: 2012Employees: 300+ nationwide

EEO Statement

Aptive is an equal opportunity employer. We consider all qualified applicants for employment without regard to race, color, national origin, religion, creed, sex, sexual orientation, gender identity, marital status, parental status, veteran status, age, disability, or any other protected class.

Veterans, members of the Reserve and National Guard, and transitioning active-duty service members are highly encouraged to apply.

Employment Type: PART_TIME

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