Sales Associate (Illinois) Remote, Chicago, IL

Remote Full-time

Job Opportunity: Sales Associate at Imagine Learning


Location: Remote (Must reside in Chicago, IL, or surrounding suburbs)
Employment Type: Full-Time
Compensation: $69,886 - $70,000 annually (plus potential incentives/commissions/bonuses based on individual and company performance)
Travel: Up to 75% travel (includes overnight and occasional weekend travel).

About Imagine Learning


Imagine Learning creates educational solutions that empower students and educators, fostering joyful learning moments. We are a remote-friendly company offering a dynamic culture that values growth, flexibility, and collaboration. With offices across the U.S., including Tempe, AZ (headquarters), Austin, TX, and Grand Rapids, MI, we provide meaningful work opportunities and a supportive team environment.

Position Summary


As a Sales Associate, you will support Account Executives in your region by conducting sales presentations, generating leads, attending trade shows, and collaborating with the sales team to meet and exceed sales goals. Your role will involve maintaining client relationships and expanding marketing presence while traveling extensively to engage with clients.

Key Responsibilities



  • Prepare and deliver sales presentations (live and virtual via Zoom).

  • Attend industry trade shows and conferences to build client relationships and gather leads.

  • Maintain client information in company databases and provide reports to Account Executives.

  • Generate leads, negotiate contracts, and finalize sales agreements.

  • Collaborate with marketing to improve promotional materials and expand territorial reach.

  • Conduct field visits to evaluate client needs and promote Imagine Learning’s products and services.

  • Assist in determining pricing schedules for quotes, promotions, and negotiations.

  • Stay updated on industry trends and adapt sales strategies to foster growth.


Technical Proficiency



  • Proficient in Microsoft Word, Excel, PowerPoint, and Outlook.

  • Experience with NetSuite and online meeting platforms (e.g., Zoom) is preferred.


Interpersonal Skills



  • Strong verbal and written communication, presentation, and organizational skills.

  • Ability to engage with decision-makers and provide excellent customer service.

  • Self-motivated, detail-oriented, and able to manage multiple priorities under tight deadlines.


Additional Requirements



  • Valid driver’s license and clean driving record.

  • Flexibility to travel up to 75% with overnight stays.

  • Ability to work independently while contributing to a team-driven environment.

  • Fingerprint clearance may be required.


  • High school diploma or equivalent (Bachelor’s degree preferred).

  • Previous experience in customer service, preferably in the travel or airline industry.

  • Strong verbal and written communication skills.

  • Proficiency in using computers, including familiarity with CRM systems and Microsoft Office.

  • Ability to multitask and work in a fast-paced environment.

  • Strong problem-solving skills and a customer-first mindset.

  • Reliable internet connection and a quiet workspace free from distractions.



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