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

Trilogy; Connecticut; Remote; USD 125,000 - 150,000; Full time

Job summary

Join a forward-thinking startup revolutionizing K-12 education through AI-driven personalized learning. As a Regional Sales Director, you'll leverage your extensive network and sales expertise to secure multi-year partnerships with school districts, driving transformative educational outcomes. This dynamic role offers autonomy and the opportunity to make a significant impact in the education sector. If you're a proven sales leader ready to close seven-figure deals and help reshape the future of learning, this is your chance to excel in a supportive, innovative environment.

Qualifications

• 3+ years managing complex K-12 sales cycles.
• Strong network with district decision-makers in TX or CA.

Responsibilities

• Build and maintain a $10M+ pipeline in K-12 education.
• Drive all aspects of complex sales cycles from prospecting to closing.

Skills

K-12 sales experience

Relationship building

Negotiation skills

CRM proficiency

Education

Bachelor's degree

Tools

CRM tools

Job description

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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

$100.00/hr - $100.00/hr

Are you a proven K-12 sales leader ready to close $2M+ in annual revenue by selling the most effective learning intervention in education? This isn't about pushing another supplemental tool - you'll be driving seven-figure partnerships that help students master curriculum using breakthrough AI technology.

Our stealth-mode startup is revolutionizing K-12 education with personalized learning technology that delivers unprecedented results. We're expanding rapidly into public school districts and need exceptional sales leaders who bring deep relationships with district decision-makers and a track record of navigating complex procurement processes. You'll have full ownership of your territory, backed by compelling data showing our AI-powered platform helps struggling students catch up while challenging advanced learners to excel - making it a perfect fit for districts looking to improve student outcomes at all levels.

We're seeking top performers with strong connections to TX or CA school districts who thrive on autonomy and are motivated by the opportunity to fundamentally change how students learn. This is your chance to build something extraordinary with the agility of a startup and the credibility of proven results.

If you're ready to close seven-figure deals that transform education while building your own success story, we want to talk to you.

What You Will Be Doing

• Build and maintain a $10M+ pipeline by identifying and qualifying high-potential districts, engaging decision-makers, and progressing opportunities through defined sales stages
• Deliver tailored proposals and navigate procurement processes to secure six and seven-figure contracts
• Lead discovery meetings to deeply understand district challenges and goals, then craft compelling solutions that deliver measurable outcomes
• Drive all aspects of complex sales cycles from prospecting through closing, with full ownership of territory strategy and results
• Leverage your existing relationships and networks within public school districts to accelerate adoption
  
  

What You Won’t Be Doing

• Following rigid scripts or processes - you'll have the autonomy to build your territory strategy
• Selling "nice to have" supplemental products - this is a transformative solution with measurable impact
• Getting bogged down in bureaucracy - we're a nimble startup focused on results
• Micromanaging day-to-day activities - you'll own your outcomes
  
  

Regional Sales Director Key Responsibilities

Drive adoption of our breakthrough learning solution in public school districts, securing multi-year partnerships that help transform educational outcomes at scale.

Basic Requirements

• 3+ years experience managing complex K-12 sales cycles and closing $100K+ deals
• Strong existing network of district decision-maker relationships in Texas or California
• Proven ability to navigate public school procurement processes including RFPs/RFIs
• Track record maintaining $10M+ sales pipeline and consistently hitting revenue targets
• Demonstrated success operating autonomously and driving full sales cycle
• Proficiency with CRM tools and sales technology stack
• Must reside in or within 2 hours of Texas or California
• Ability to travel extensively within the region (up to 80%)
• Eligible to work in the US without visa sponsorship
  
  

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 $100 USD/hour, which equates to $200,000 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-5513-US-Connecti-RegionalSalesD.002

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Business Development, Project Management, and Sales

• Industries

  Software Development, E-Learning Providers, and Primary and Secondary Education

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