ZipRecruiter

Log In

2

Entry Level Pilot Jobs in Chicago, IL (NOW HIRING)

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL

$55K - $65K/yr

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

W S DARLEY & CO

Uncrewed Systems Specialist

Itasca, IL

$55K - $65K/yr

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

W S Darley & Co

Uncrewed Systems Specialist

Itasca, IL · On-site

$55K - $65K/yr

The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This ... Position Type, Expected Hours of Work, and Travel This is a full-time, entry-level position. Days ...

Resource Hub

Inventory Specialist

Elmhurst, IL · On-site

$21 - $28/hr

... entry-level roles to certified ATP support and beyond. Compensation: * Hourly Pay: $21-$28 ... Update the equipment ordering queue in Sales Pilot Purchasing & Inventory Performance Metrics

All JobsPilot JobsEntry Level Pilot JobsEntry Level Pilot Jobs in Chicago, IL

Entry Level Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do entry level pilot jobs pay per year?

As of Jul 31, 2026, the average yearly pay for entry level pilot in Chicago, IL is $134,863.00, according to ZipRecruiter salary data. Most workers in this role earn between $103,000.00 and $159,700.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an Entry Level Pilot, and why are they important?

To thrive as an Entry Level Pilot, you need a solid understanding of aerodynamics, navigation, and flight operations, typically backed by a commercial pilot’s license and completed flight training hours. Familiarity with aviation software, flight management systems (FMS), and aircraft-specific instrumentation is commonly required. Strong situational awareness, decisive communication, and the ability to remain calm under pressure are crucial soft skills for this role. These competencies ensure safe, efficient flight operations and effective responses to dynamic in-flight situations.

What Does an Entry-Level Pilot Do?

An entry-level pilot has the same responsibilities as any other pilot, which are to ensure that an airplane takes off, travels, and lands safely. In this position, you may work as a copilot or flight engineer in addition to your duties as a pilot, depending on the need of the airline. These duties include checking that all flight instrumentation is working, performing safety and maintenance checks with other airplane technicians, and filing flight route plans. In the air, you ensure that the plane remains in communication with ground control.

What are entry level pilots?

Entry level pilots are individuals who have recently earned their pilot licenses and are beginning their professional aviation careers. They typically hold a commercial pilot certificate and may work in roles such as flight instructors, regional airline first officers, or charter pilots. Entry level pilots are responsible for flying aircraft safely, following regulations, and gaining experience to qualify for more advanced positions. These pilots often use their initial jobs to build flight hours, develop skills, and advance to higher positions within the aviation industry.

What are the typical training and mentorship opportunities available to entry level pilots starting their careers?

Entry level pilots generally undergo structured training programs that combine classroom instruction, simulator sessions, and supervised flight hours. New pilots often work closely with experienced captains and instructors who provide mentorship and guidance during the initial phases of their careers. Many airlines and flight schools also offer ongoing education and recurrent training to ensure pilots remain current with regulations and best practices. This supportive environment helps entry level pilots build confidence, refine their flying skills, and progress toward more advanced roles.

What is the difference between Entry Level Pilot vs Flight Instructor?

AspectEntry Level PilotFlight Instructor
Required CertificationsPrivate Pilot License (PPL), Commercial Pilot License (CPL)Certified Flight Instructor (CFI), CPL
Work EnvironmentAirlines, charter services, cargo carriersFlight schools, training aircraft
Industry UsageEntry-level commercial flying rolesTraining new pilots, gaining flight hours

Entry Level Pilots typically hold PPL and CPL licenses, working in commercial flying roles. Flight Instructors also hold CFI certification and focus on training pilots, often as a stepping stone to higher flying positions. Both roles require similar licenses but differ in work environment and primary responsibilities.

More about Entry Level Pilot jobs
What are the most commonly searched types of Pilot jobs in Chicago, IL? The most popular types of Pilot jobs in Chicago, IL are:
What job categories do people searching Entry Level Pilot jobs in Chicago, IL look for? The top searched job categories for Entry Level Pilot jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Entry Level Pilot jobs? Cities near Chicago, IL with the most Entry Level Pilot job openings:
Entry Level Pilot jobs near you
Infographic showing various Entry Level Pilot job openings in Chicago, IL as of July 2026, with employment types broken down into 86% Full Time, 11% Part Time, 1% Temporary, and 2% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $134,863 per year, or $64.8 per hour.

Uncrewed Systems Specialist

W S DARLEY & CO

Itasca, IL

$55K - $65K/yr

Other

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 25 days ago

Job description

Description

We are looking for an Uncrewed Systems Specialist to join our incredible team!


The Uncrewed Systems Specialist will provide technical, piloting, and sales support. This individual serves as the initial point of contact for users encountering issues with UAS hardware, software, or operations. In addition to providing prompt technical support and ensuring smooth system performance, this role also supports live demonstrations as a drone pilot, showcasing system capabilities to customers and stakeholders. The position plays a key role in business development efforts, assisting with customer engagement, product demonstrations, and supporting growth initiatives within the uncrewed systems market.


About W.S. Darley & Co: Founded in 1908, W.S. Darley & Co. (Darley) remains a family owned and operated business, supplying the highest quality equipment solutions to its military and first responder customers. With origins in the equipment distribution and Midwest manufacturing, Darley offers a family of leading innovate emergency equipment brands and innovative solutions. Darley prides itself on delivering the highest quality solutions and services from its corporate headquarters in Itasca, IL and its' ISO 9001:2015 certified manufacturing operations in Chippewa Falls, WI and Janesville, IA.

Requirements

1. Troubleshooting & Operational Support

  • Diagnose and resolve common UAS hardware, software, and integration issues to ensure mission readiness
  • Provide timely technical support while maintaining a strong customer-facing presence during operational use
  • Serve as a drone demo pilot, conducting live flight demonstrations to showcase UAS capabilities to prospective customers

2. Sales & Business Development

  • Partner with Sales and Business Development teams to drive customer engagement and support revenue growth initiatives
  • Translate technical product capabilities into clear, mission-focused value propositions for customers
  • Collaborate internally to develop tailored UAS solutions aligned with customer requirements
  • Support responses to RFPs, RFIs, and government procurements, contributing detailed technical input
  • Actively participate in tradeshows, customer demos, and field events, representing the company and promoting product offerings
  • Assist with pipeline development, customer follow-ups, and opportunity advancement

3. Pre-Shipping Quality & Demo Readiness

  • Perform QA checks on UAS platforms, payloads, and software before shipment or demo deployment
  • Maintain all systems with current firmware and configurations to ensure demo and delivery readiness

4. Documentation & Knowledge Management

  • Document customer interactions, issues, and resolutions in ticketing systems
  • Develop and maintain internal knowledge bases and technical documentation
  • Assist in creating and updating SOPs for support, demo operations, and customer engagement

5. Escalation & Coordination

  • Escalate complex technical issues to Level 2/3 support while maintaining communication with customers
  • Track and follow up on escalated issues to ensure resolution and strong customer experience

6. Customer Engagement & Field Support

  • Communicate effectively with customers, providing clear technical guidance and support
  • Lead and support live demonstrations as a pilot, ensuring safe, effective, and compelling presentations
  • Engage customers to understand operational challenges and recommend optimized UAS solutions
  • Follow up post-engagement to ensure satisfaction and gather feedback to support future sales efforts

7. Demo Fleet & Asset Management

  • Maintain demo fleet systems in fully operational, flight-ready condition
  • Track and manage all assigned UAS assets using asset management systems

8. Company Representation

  • Represent the company professionally at customer sites, demos, and events
  • Clearly communicate the value, differentiators, and mission impact of solutions

Supervisory Responsibility

This position currently has no supervisory responsibility.


Work Environment and Physical Demands

This job operates in a professional office environment. This role routinely uses company standard office equipment such as computers and cell phones. There may be a need to work with various small tools. There may be a need for remote work in the field for hands-on assistance and maintenance. The employee will be required to sit or stand for extended periods, use a computer keyboard, use hand tools, and occasionally lift and carry equipment and supplies weighing up to 25 pounds. The employee must be able to push or pull carts weighing more than 70lbs.


Position Type, Expected Hours of Work, and Travel

This is a full-time, entry-level position. Days and hours of work are Monday through Friday, 8:00 a.m. to 4:30 p.m. or as otherwise required. 


Education

While not strictly required, a bachelor's degree in a technical field is often preferred. 


Preferred Technical Knowledge

A deep understanding of drone workings, components, systems, and software

Familiarity with UAS operations (a plus) - understanding drone operation, regulations, and terminology


Experience

  • 1-4 years in sales and/or uncrewed industry or similar
  • Part 107 Certification is preferred, but not required
  • Customer support/success or similar experience

Skills

  • Communication Skills- excellent verbal and written communication skills are essential for effectively conveying technical information to both technical and non-technical audiences
  • Interpersonal Skills- building a rapport and trust with clients is vital for successful interactions
  • Problem-Solving Skills- ability to analyze and resolve technical problems efficiently and effectively
  • Presentation Skills- ability to deliver clear and compelling presentations to both technical and non-technical audiences is essential
  • Technical Proficiency- a strong understanding of UAS technology and related products and software
  • Project Management Skills- manage multiple projects simultaneously, requiring strong organizational skills
  • Attention to detail- meticulousness in documenting issues, solutions, and procedures accurately
  • Teamwork- work closely with sales teams, product development teams, and stakeholders, requiring strong teamwork and collaboration skills
  • Adaptability- ability to learn quickly and adapt to new technologies and customer needs
  • Customer Focus- a strong focus on understanding and meeting customer needs is crucial for success

Benefits

  • PTO
  • Paid Holidays
  • Tuition Reimbursement
  • Health & Wellness Reimbursement
  • Medical
  • Dental
  • Vision
  • Life & Disability
  • HSA with Darley contribution
  • FSA
  • 401K/Roth with match and profit sharing
  • Darley paid life insurance

Compensation


$55,000 to $65,000


AAP/EEO Statement

Darley is an equal opportunity organization. We recruit, employ, train, compensate, and promote without regard to race, religion, color, national origin, age, gender, sexual orientation, gender identity, marital status, disability, protected veteran status, or any other basis protected by applicable federal, state, or local law

Apply