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Temporary Multi Engine Pilot Jobs in Illinois (NOW HIRING)

World Book

ClassMate Sales Manager

Chicago, IL · On-site

$115K/yr

... the sales engine that will put it in classrooms across the country. We're looking for a Sales ... multi-stakeholder buying committees, RFPs, pilots, and board approvals. * Fluency with the K-12 ...

Ovative group

Lead AI Engineer

Chicago, IL

$105K - $139K/yr

... Engine Land. About the Role: Most companies are still figuring out what it means to be AI-native ... Not a pilot. Nota proofof concept. A production system that changes how an entire ...

Firstup

Head of Marketing Operations

Chicago, IL

$140K - $155K/yr

The Marketing Operations Lead is the strategic architect of Firstup's marketing engine, responsible ... Design and maintain comprehensive multi-touch attribution models that connect marketing activities ...

Firstup

Head of Marketing Operations

Chicago, IL

$140K - $155K/yr

The Marketing Operations Lead is the strategic architect of Firstup's marketing engine, responsible ... Evaluate, pilot, and implement AI-powered solutions across the marketing tech stack-including ...

Instawork

General Manager, Data Centers

Chicago, IL

$160K - $200K/yr

... engine. * Strategic Execution & Partnership Expansion: Refine and implement Instawork's growth ... Multi-disciplinary Executor: You have a proven track record of managing high-growth expansion ...

HUB

Product Manager, AI & Marketing Technology

Chicago, IL

$158K/yr

... pilot projects to systemic, owned infrastructure * Manage the Marketing AI intake, triage and ... Help identify transformational, multi-step AI initiatives, in partnership with the VP MarTech Stack ...

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Temporary Multi Engine Pilot information

What is a temporary multi engine pilot?

Temporary Multi Engine Pilots are licensed pilots who are hired on a short-term basis to operate aircraft with more than one engine. They may be contracted for specific assignments, such as seasonal work, special projects, or to cover staffing shortages. These pilots must hold a valid multi-engine rating and often a commercial pilot license. Their duties include safely operating multi-engine planes, conducting pre-flight checks, and following all aviation regulations. The temporary nature of their role allows flexibility for both the pilot and the employer.

What is the difference between Temporary Multi Engine Pilot vs Commercial Pilot?

AspectTemporary Multi Engine PilotCommercial Pilot
CertificationsMulti-engine rating, Commercial Pilot CertificateCommercial Pilot Certificate, often with multi-engine rating
Work EnvironmentShort-term contracts, charter flights, trainingScheduled flights, charter, cargo, passenger services
Employer & IndustryFlight schools, charter companies, private operatorsAirlines, charter services, cargo carriers

Temporary Multi Engine Pilots typically hold the same certifications as Commercial Pilots but work on short-term or contract basis, often in training or charter roles. Commercial Pilots have broader responsibilities and may work full-time for airlines or larger operators. Both roles require similar credentials, but their employment types and work environments differ.

What are some common challenges faced by temporary multi engine pilots, and how can they be managed effectively?

Temporary Multi Engine Pilots often face challenges such as adapting quickly to new aircraft, operational procedures, and team dynamics, since assignments may vary in duration and location. Managing these challenges requires strong foundational knowledge, adaptability, and effective communication with ground and flight crews. Staying up-to-date with regulatory requirements and maintaining a high level of proficiency in multi-engine operations are also key. Building rapport quickly with new teams and being proactive in familiarizing oneself with company-specific protocols can greatly enhance both performance and safety.

What are the key skills and qualifications needed to thrive as a temporary multi engine pilot?

To thrive as a Temporary Multi Engine Pilot, you need an FAA commercial pilot certificate with multi-engine rating and significant flight hours in multi-engine aircraft. Proficiency with advanced avionics, navigation systems, and adherence to safety protocols are crucial, with some employers requiring type ratings or instrument ratings. Exceptional situational awareness, quick decision-making, and strong communication skills help you excel, especially when flying as part of a crew or under dynamic conditions. These competencies ensure operational safety, regulatory compliance, and effective management of complex flight scenarios.
What are the most commonly searched types of Multi Engine Pilot jobs in Illinois? The most popular types of Multi Engine Pilot jobs in Illinois are:
What cities in Illinois are hiring for Temporary Multi Engine Pilot jobs? Cities in Illinois with the most Temporary Multi Engine Pilot job openings:
Temporary Multi Engine Pilot jobs near you

ClassMate Sales Manager

World Book

Chicago, IL • On-site

$115K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 7 hours ago

Job description

About the role
ClassMate is World Book's next-generation K-12 instructional platform - and we're building the sales engine that will put it in classrooms across the country. We're looking for a Sales Manager who has the drive to build the team and leads it to a scaled, repeatable revenue motion.
This is a player-coach role. You'll carry a personal book of strategic accounts and run point on our most consequential deals; you'll also lead a team of National Account and Bottoms-up Sellers. You'll own the team's quota, the forecast it rolls up to, and the playbook that gets us there.
You know what it takes to navigate long cycle district buyers and capitalize on high velocity school deals. You're as comfortable opening a CAO conversation as you are coaching a rep through their pipeline review. If that sounds like you, this role was built for you.
What you'll do
Carry your own quota
  • Own a personal book of strategic district accounts - typically the most complex, highest-value opportunities in the pipeline.
  • Run executive-level conversations with Superintendents, CAOs, Directors of Curriculum, and CTOs. Build multi-threaded relationships across cabinet and committee.
  • Personally drive deals through Discovery, Evaluation, Vendor Selection, and Procurement - including RFP responses, pilot design, and board-approval support.

Lead and coach the team
  • Manage and develop a team of four sellers operating across National Accounts, Large/Mid Districts, Small Districts, and individual Schools.
  • Coach reps through the realities of K-12 selling: 12-24 month district cycles, July 1 fiscal-year timing, board approvals, multi-stakeholder consensus, and the very different velocity of school-level deals.
  • Run weekly 1:1s, pipeline reviews, and deal strategy sessions. Build sellers who can navigate from classroom champion to cabinet sponsor.
  • Own hiring, ramping, and performance management. Identify when to scale the team up - and when a rep needs a new plan to get back on track.

Own pipeline, forecast, and revenue plan
  • Drive pipeline coverage discipline. Ensure each rep is building enough qualified pipeline (Discovery and beyond) to clear quota with appropriate stage-weighted coverage.
  • Run a clean Salesforce instance: stage hygiene, BANT qualification, next steps, close-date discipline. The forecast is only as good as the data. Build and defend an accurate forecast.
  • Surface risk early. When pipeline maturity signals trouble against the plan, you'll be the first to call it and propose the response.

Partner cross-functionally to sharpen GTM
  • Work with Marketing to refine ICP targeting, messaging, and demand-gen plays across the four buying segments.
  • Partner with Product to feed field intelligence into the roadmap - what's winning deals, what's losing them, and what gaps competitors are exploiting.
  • Iterate on sales scripts, discovery frameworks, demo flows, and competitive positioning. Translate what works in the field into a repeatable team playbook.
  • Coordinate with Customer Success and Training to ensure clean handoffs and renewal-ready accounts.

What you bring
Required experience
  • 6+ years of K-12 EdTech sales experience, with a strong track record selling instructional or curriculum solutions into school districts.
  • 2+ years of direct sales management experience - hiring, coaching, and managing quota-carrying reps to plan.
  • Demonstrated success closing complex district deals ($100K+) with multi-stakeholder buying committees, RFPs, pilots, and board approvals.
  • Fluency with the K-12 buying cycle - needs assessment, goal setting, vendor evaluation, procurement - and the personas who drive each stage (Superintendent, CAO, Director of Curriculum, Director of Instructional Technology, Principal, Instructional Coach).
  • Salesforce proficiency: stage management, forecasting, pipeline analytics, and rep accountability.

How you operate
  • Player-coach mindset. You can close a deal on Tuesday and run a rep's pipeline review on Wednesday without dropping either one.
  • Forecast discipline. You believe a missed forecast is a process problem, not a luck problem - and you build the systems to fix it.
  • Coaching instinct. You'd rather make a rep great than do their job for them. You give direct feedback and you make it stick.
  • Cross-functional credibility. Marketing, Product, and CS partners want you in the room because you bring sharp field signal, not just complaints.
  • Comfort with ambiguity. ClassMate is a growing product line - you're as ready to write the playbook as to run it.

Why ClassMate
World Book has been a trusted name in K-12 education for over a century. ClassMate is how we bring that legacy into the AI-enabled classroom - built specifically for middle school instruction, with the rigor educators expect and the student experience to drive real learning outcomes.
You'll join at a moment when the product is real, the pipeline is building, and the next chapter of the company is being written by the people in the room. If you want to sell something educators are excited about, lead a team that's hungry to win, and help shape how a category-defining product gets to market - let's talk.
Compensation and logistics
  • Base salary: $115,000
  • Variable compensation tied to team quota attainment and personal quota performance.
  • Comprehensive benefits: medical, dental, vision, 401(k) with match, paid time off, and professional development support.
  • Location: Fully remote within the U.S. Travel expected for district visits, conferences, and team meetings - typically 25-35%, weighted toward Q1-Q2 buying season.
  • Reports to: Vice President of Sales

World Book is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

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