Hourly Multi Engine Pilot Jobs in Chicago, IL (NOW HIRING)

About the role

ClassMateis World Book's next-generation K-12 instructional platform - andwe'rebuilding the sales engine that will put it in classrooms across the country.We'relooking for aSalesManagerwhohas the drive tobuild the teamand leads it to a scaled, repeatable revenue motion.

This is a player-coach role.You'llcarry a personal book of strategic accounts and runpointon our most consequentialdeals;you'llalso leada team ofNational Account and Bottoms-up Sellers.You'llown the team's quota, the forecast it rolls up to, and the playbook that gets us there.

Youknowwhat it takestonavigatelongcycledistrict buyersandcapitalize on high velocityschool deals.You'reascomfortable 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.

Whatyou'lldo

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 acrosscabinetandcommittee.

• 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 offoursellersoperatingacross National Accounts, Large/Mid Districts, Small Districts, and individual Schools.

• Coach reps through the realities of K-12 selling:12-24 monthdistrict cycles, July 1 fiscal-year timing, board approvals, multi-stakeholder consensus, and thevery differentvelocity 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.Identifywhen 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 withappropriate stage-weightedcoverage.

• 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 defendan accurateforecast.

• Surface risk early. When pipeline maturity signals trouble against the plan,you'llbe the first to call it and propose the response.

Partner cross-functionally to sharpen GTM

• Work withMarketingto refine ICP targeting, messaging, and demand-gen plays across the four buying segments.

• Partner withProductto feed field intelligence into the roadmap - what's winning deals,what'slosing 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 withCustomer SuccessandTrainingto ensure clean handoffs and renewal-ready accounts.

What you bring

Required experience

• 6+ yearsof K-12 EdTech sales experience, with a strongtrack recordselling instructional or curriculum solutions into school districts.

• 2+ yearsof 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).

• Salesforceproficiency: stage management, forecasting, pipeline analytics, and rep accountability.

How you operate

• Player-coach mindset.You can close a deal on Tuesday and run arep'spipeline 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.

• Coachinginstinct.You'drather make a rep great than do their job for them. You give direct feedbackand youmake it stick.

• Cross-functional credibility.Marketing, Product, and CS partners want you in the room because you bring sharp fieldsignal, not just complaints.

• Comfort with ambiguity.ClassMateis a growing product line -you're asready to write theplaybook asto run it.

WhyClassMate

World Book has been a trusted name in K-12 education for over a century.ClassMateis how we bring that legacy into the AI-enabled classroom - built specifically for middle school instruction, with the rigor educatorsexpectand the student experience to drive real learning outcomes.

You'lljoin 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 teamthat'shungry to win, and help shape how a category-defining product gets to market -let'stalk.

Compensation andlogistics

• 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 - typically25-35%, 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.