Sales Director, 2 Hour Learning (Remote) - $400,000/year USD
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This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.
Base pay range $200.00/hr - $200.00/hr
Education isn't broken because it's too hard. It's broken because it's too slow.
At 2 Hour Learning, we've reimagined what's possible when we stop wasting students' time. Our revolutionary model delivers a complete academic day in just two hours through AI-powered tutoring, mastery-based progression, and ruthless efficiency. The results speak volumes: MAP scores in the top 1%, SAT averages exceeding 1450, and students who finally have time to develop real-world skills that matter.
This isn't education with a digital veneer. This is a fundamental rebuild of learning from first principles. We embrace rigorous testing. We celebrate measurable outcomes. And we refuse to dilute excellence in the name of comfort.
If you believe children deserve to be challenged rather than coddled, if you're convinced that data trumps educational dogma, and if you're prepared to champion a vision that many find uncomfortably ambitious – we need your voice.
As our Sales Director, you'll become the commanding presence behind our microschool revolution. You'll captivate high-net-worth families across 25+ cities, dominate podcast interviews, craft compelling written content, and ensure every public-facing message maintains our uncompromising standard of excellence. While marketing and PR will support you, the authority and impact of our message rests squarely on your shoulders.
Your mission transcends traditional sales. You'll be the catalyst that transforms interest into enrollment, skepticism into conviction, and polite curiosity into passionate advocacy. When necessary, you'll dive deeper into the conversion funnel, guiding families through their decision journey and ensuring our enrollment teams maintain our exacting standards.
Ready to dismantle educational mediocrity? This is your platform to lead the charge.
What You Will Be Doing
Orchestrating high-impact, persuasive events that convert discerning, high-net-worth families into 2HL believers
Becoming the face and voice of 2HL across media channels – from podcast interviews and blog contributions to video content, press engagements, and conference keynotes
Providing strategic intervention throughout the conversion funnel when exceptional quality or credibility is required
Transforming hard performance metrics and student achievement data into compelling narratives that resonate with sophisticated audiences
Elevating all external communications to meet the exacting standards of high-net-worth clientele
Establishing and enforcing an unyielding standard of excellence across all teams touching our public message
What You Won’t Be Doing
Promoting yet another tech-enhanced version of conventional private education
Diluting our message to appease parental comfort zones or educational orthodoxy
Tolerating mediocrity in marketing materials or event execution – you define excellence and demand it
Managing technical marketing operations like digital ad campaigns, lead generation, or enrollment system administration
Functioning in traditional school administrative or curriculum development capacities
Sales Director Key Responsibilities
Catalyze enrollment growth by embodying and amplifying 2 Hour Learning's distinctive voice, establishing an uncompromising standard for every narrative we craft and every audience we engage.
Basic Requirements
U.S.-based professional with comprehensive understanding of the educational landscape and a bold perspective on necessary reforms
Minimum 5 years of experience in high-impact, persuasive roles (founder, media personality, professional speaker, or strategic sales leadership)
Demonstrated success influencing executive-level decision makers and high-net-worth individuals
Exceptional ability to maintain message integrity, quality standards, and brand voice, even when facing internal resistance
Demonstrated capacity to navigate all stages of prospect engagement beyond just content creation or presentation delivery
Personal conviction about elevating educational standards and student achievement
Availability for up to 50% travel and flexibility for hybrid or in-person work arrangements
Valid U.S. work authorization (sponsorship not available)
Nice-to-have Requirements
Professional background in premium education sectors, media production, or issue-based advocacy
Knowledge of accelerated learning methodologies, mastery-based education, or gifted/talented programming
About 2 Hour Learning
Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.
With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.
They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.
2 Hour Learning is reprogramming learning for the AI era.
Here’s How They’re Fixing It.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-4796-US-Chicago-SalesDirector.013
Seniority level Seniority level Executive
Employment type Employment type Full-time
Job function Job function Business Development, Engineering, and Sales
Industries Software Development, IT Services and IT Consulting, and Advertising Services
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- Location:
- Chicago, IL, United States
- Salary:
- $200,000 - $250,000
- Job Type:
- FullTime
- Category:
- Sales