ZipRecruiter

Log In

1

Second In Pilot Jobs in Chicago, IL (NOW HIRING)

FleetWorks

Senior Customer Success Manager

Chicago, IL · On-site

As the second member of the customer success team, you will be a true owner of your work, managing ... Program manage high-stakes pilots and implementations , ensuring timelines are met and customers ...

Woodward, Inc.

Welder - Hiring Now

Niles, IL

$16.49 - $28.60/hr

... * 2nd Shift Hours: 4:00pm-12:30am * 10% shift differential * All members included in annual cash ... You will play a key role on a team that produces pilot controls, electromechanical actuators ...

Woodward, Inc.

Welder - Submarine Building

Niles, IL

$16.49 - $28.60/hr

... * 2nd Shift Hours: 4:00pm-12:30am * 10% shift differential * All members included in annual cash ... You will play a key role on a team that produces pilot controls, electromechanical actuators ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Berwyn, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

Iberia Express

CDL A Drivers

Chicago, IL

$6.0K/wk

Layover pay beginning on the second day * Extra stop pay * DOT inspection bonuses * Safety bonuses ... Best-in-class fuel discounts * Toll and truck stop network access including Loves, Pilot, Flying J ...

next page

Showing results 1-20

All JobsSecond In Pilot JobsSecond In Pilot Jobs in Chicago, IL

Second In Pilot information

See Chicago, IL salary details

$51K

$134.9K

$207.1K

How much do second in pilot jobs pay per year?

As of Jun 17, 2026, the average yearly pay for second in 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 some common challenges faced by a Second In Pilot, and how can they be addressed?

Second In Pilots often face challenges such as adapting to varying flight schedules, maintaining situational awareness under pressure, and efficiently communicating with the Captain and crew. It's essential to stay up-to-date with standard operating procedures and regularly participate in simulator training to sharpen decision-making skills. Building strong teamwork and clear communication habits with other crew members also helps address these challenges and supports safe, efficient flight operations.

What is the difference between Second In Pilot vs First Officer?

AspectSecond In PilotFirst Officer
CertificationsCommercial Pilot License (CPL), Second In Pilot certificationCommercial Pilot License (CPL), First Officer certification
Work EnvironmentAssists the Captain, operates as part of the flight crewShares flying duties, supports the Captain
Role in FlightSupports the Captain, may handle specific flight segmentsPrimary pilot during flight, responsible for navigation and safety

The Second In Pilot and First Officer roles are both essential flight crew positions requiring similar certifications. The Second In Pilot typically assists the Captain and may operate specific flight segments, while the First Officer is the primary pilot during flight, sharing flying duties and decision-making responsibilities. Both roles work closely within the cockpit, but the First Officer often has more flying authority and experience.

How long does it take to make $200,000 as a pilot?

A second in pilot typically earns an hourly wage that, with consistent flying hours and experience, can lead to earning $200,000 in several years. Factors such as airline pay scales, flight hours, and seniority influence the timeline, with many pilots reaching this income level after 5 to 10 years of service. Building flight hours, obtaining necessary certifications, and gaining experience are essential steps toward higher earnings.

What are the key skills and qualifications needed to thrive as a Second In Pilot, and why are they important?

To excel as a Second In Pilot (First Officer), you need a valid commercial pilot license, strong aeronautical knowledge, and experience with flight operations. Familiarity with flight management systems (FMS), aircraft-specific avionics, and regulatory compliance tools is typically required, along with certifications such as an Airline Transport Pilot License (ATPL). Excellent communication, teamwork, and decision-making skills help you coordinate effectively with the captain and crew, especially under pressure. These competencies are crucial for ensuring flight safety, regulatory adherence, and smooth operation of commercial flights.

What are Second In Pilots?

A Second In Pilot, often referred to as a First Officer or Co-Pilot, is a licensed pilot who assists the Captain (Pilot in Command) in operating an aircraft. They share flying duties, help with navigation, communication, and monitoring aircraft systems. Second In Pilots are essential for ensuring flight safety, supporting the Captain, and stepping in to take control if necessary. They also play a significant role in pre-flight checks, emergency procedures, and communicating with air traffic control.

What is the 2 pilot rule?

The 2 pilot rule in aviation requires that two qualified pilots are present in the cockpit during flight, ensuring safety and compliance with regulations. For second in pilots, this often means they must be properly trained, certified, and capable of taking over flying duties if needed, especially on commercial or complex flights.

Can an airline pilot have a second job?

Airline pilots, including second-in pilots, can have a second job if it does not interfere with their flight duties, adherence to FAA or relevant aviation authority regulations, and company policies. However, they must ensure their secondary employment does not compromise safety, alertness, or violate conflict-of-interest rules. Many airlines require disclosure of additional employment for safety and scheduling reasons.

Which pilots make 500,000 a year?

Second In Pilots, typically experienced airline captains or senior pilots at major airlines, can earn $500,000 or more annually through base salary, overtime, and bonuses. High earnings are often associated with large aircraft, extensive flight hours, and seniority in the airline industry.
What are popular job titles related to Second In Pilot jobs in Chicago, IL? For Second In Pilot jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Second In Pilot jobs in Chicago, IL look for? The top searched job categories for Second In Pilot jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Second In Pilot jobs? Cities near Chicago, IL with the most Second In Pilot job openings:
Second In Pilot jobs near you

Senior Customer Success Manager

FleetWorks

Chicago, IL • On-site

Full-time

Medical, Dental, Vision

Posted 25 days ago

Job description

Every year, companies spend over a trillion dollars moving freight across the U.S. - but the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that.
We're building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved.
As the second member of the customer success team, you will be a true owner of your work, managing our most critical relationships and defining the customer success motion from the ground up.
What you'll do
  • Manage the full customer lifecycle, acting as the primary owner from pilot kickoff through implementation, adoption, and renewal.
  • Program manage high-stakes pilots and implementations, ensuring timelines are met and customers realize immediate value from our platform.
  • Work closely with Engineering to scope and deliver on individual customer integration requirements, acting as the technical voice of the customer.
  • Build the CS foundation (0-to-1) by creating documentation, establishing operating procedures, and designing the engagement cadences we need to scale.
  • Drive ongoing customer education, ensuring users understand the full power of our voice agents and platform features.
  • Learn from others and teach those around you.

What we look for
  • Professional experience in b2b customer success, account management, sales engineering or implementation, in an entrepreneurial environment.
  • Must have Enterprise level freight tech experience, you will be managing large, multithreaded broker accounts and smaller firms.
  • A "builder" mindset: You are excited to be the second member of the team and want to work on 0-1 projects like building playbooks and defining processes.
  • Technical aptitude: You are comfortable working hands on with complex requirements gathering and configurations and collaborating with engineers to make sure we deliver on our promise.
  • A healthy appreciation for hard problems-we are transforming a massive, complex industry and we're just getting started.

How we'll get to know each other
  • 45 minute intro call, what you've worked on that you're proud of, your goals and motivations and to figure out how that might fit in with what we're working on at FleetWorks.
  • 45-min interview with a team member you'll work with if you join, so that we can get to know how you think about customer success and collaboration.
  • Case study or presentation to see how you approach customer challenges.
  • Paid onsite work trial so that we can get to know how you work and you can get to know us.
  • We'll talk with your references to help us understand how to best support your development at work-we might do this after you've signed your offer.
  • Transparent offer process that clearly outlines how we came to the compensation package we're offering, including the current and potential value of your equity.

What we offer
  • Top tier cash and equity compensation-we aim to be above 75th %ile for companies in San Francisco who have raised a similar amount of cash.
  • Competitive medical, dental, and vision benefits.
  • Fully covered lunches and dinners.
  • The opportunity to learn quickly, grow fast, and be rewarded for your contributions.

Apply