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Trilogy

Sales Director, 2 Hour Learning (Remote) - $200,000/year USD

Trilogy, Chicago, Illinois, United States

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Sales Director, 2 Hour Learning (Remote) - $200,000/year USD

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Trilogy Base pay range $100.00/hr - $100.00/hr

Overview Ready to redefine education's future? Join us to pioneer an AI-powered learning system that aims to make education twice as effective in half the time. We are seeking a visionary Sales Director to lead our expansion into the private school market with a solution that enables students to perform in the top 1-2% nationally while enjoying their educational journey. Our product stands apart in the marketplace with proven results.

Enjoy the freedom to architect your own approach with the security of a guaranteed $200K compensation package—no commission tricks or gimmicks. This stability lets you focus on creating transformative educational partnerships and building a scalable business model.

Become the driving force behind educational innovation. Your next career chapter starts here!

What You Will Be Doing

Develop and strategically manage a robust sales pipeline targeting premium private educational institutions, maintaining visibility throughout the customer journey

Deliver dynamic, persuasive presentations that highlight our learning revolution and address the needs of educational stakeholders

Independently navigate the complete sales cycle—from prospecting to deal closure—to achieve revenue objectives

Cultivate and deepen strategic relationships with key decision-makers in the private education ecosystem

Utilize our CRM to maintain meticulous records and generate accurate forecasting

What You Won’t Be Doing

Overseeing staff; this role focuses on personal sales excellence as an individual contributor

Following predetermined playbooks; you will create the roadmap for this untapped market

Relying on extensive support infrastructure for lead generation or deal completion

Marketing a conventional product in an oversaturated marketplace

Sales Director Key Responsibilities Champion revenue expansion by securing commitments for our innovative 2 Hour Learning solution within private educational institutions, establishing a formidable market footprint, and delivering sustainable year-over-year growth.

Basic Requirements

Minimum 3-year track record in B2B sales with demonstrated success in meeting or surpassing revenue objectives

Proven expertise managing end-to-end sales cycles from initial prospect identification through successful closure

Previous experience in education markets (US K-12) or related sectors such as EdTech, SaaS, or educational services strongly desired

Excellence in consultative selling approaches and relationship development

Proficiency with CRM platforms (Salesforce, HubSpot, etc.)

US-based location required

Comprehensive understanding of the American private education landscape

Willingness to travel 50-75% for client meetings and industry events

About 2 Hour Learning Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They are replacing the one-size-fits-all model with AI-driven personalized learning that helps kids master academics in just two hours a day. Students rank in the top 1-2% nationally with strong growth metrics, demonstrating smarter learning is possible. 2 Hour Learning offers a dynamic, on-campus and remote-friendly environment for innovators, educators, and AI specialists working to fix a broken school system.

2 Hour Learning is reprogramming learning for the AI era.

Working with us This is a full-time (40 hours per week), long-term position. The role is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $100 USD/hour, equating to $200,000 USD/year assuming 40 hours/week and 50 weeks/year. The payment period is weekly. For details, see www.crossover.com/help-and-faqs.

Crossover Job Code: LJ-5431-US-Cook-SalesDirector

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