Technical Operations Specialist, 2 Hour Learning (Remote) - $100,000/year USD

You are not looking to "support operations." You want to run the engine that enables a rapidly expanding education platform to onboard new schools without disrupting billing, data integrity, or launch-day readiness. If you thrive on converting chaotic, manual workflows into streamlined systems that operate autonomously, continue reading. If you prefer a constrained role where you simply execute existing playbooks, this position will not satisfy you.

2 Hour Learning is demonstrating that school can function fundamentally differently. Using an AI tutor and individualized learning pathways, students achieve mastery of core subjects in only two hours per day, with outcomes that rank students in the top 1–2% nationally. Supporting that result is a rigorous operational reality: new schools must be brought online rapidly, invoiced accurately, and tracked consistently across multiple systems and varied launch schedules.

In this position, you will be accountable for complete school onboarding operations (SIS configuration, roster management, credential provisioning, testing logistics, platform launch readiness). You will manage billing and accounts receivable using platforms such as NetSuite and Stripe. You will also construct automated data pipelines and produce weekly executive reporting by integrating tools like SIS, HubSpot, and financial systems. Your competitive advantage is automation: you will leverage AI and tools such as Python, Apps Script, Zapier, or Make to eliminate repetitive manual tasks.

If you seek quantifiable ownership, direct external customer interaction, and the authority to automate everything that should not require manual effort, submit your application.

What You Will Be Doing

• Execute complete onboarding workflows for new schools, including SIS setup, roster management, credential distribution, testing logistics (MAP/NWEA), and launch preparation
• Manage invoicing and accounts receivable operations, including payment link generation, invoice timing, reconciliation processes, and overdue balance monitoring
• Create and sustain automated reporting pipelines that consolidate data from SIS, HubSpot, NetSuite, and additional operational platforms into weekly executive summaries
• Develop and deploy automation workflows leveraging AI and tools such as Python, Apps Script, Zapier, or Make to remove recurring manual operational tasks
• Coordinate daily with school partners, finance teams, and internal stakeholders to clear obstacles and maintain progress on launches, billing cycles, and reporting timelines

What You Won’t Be Doing

• Manually recreating identical reports on a weekly basis
• Serving as a project coordinator without genuine operational accountability for results
• Performing operations that only affect internal processes while others handle actual school-facing responsibilities
• Expanding your workload by introducing additional manual tasks rather than automating the workflow

Technical Operations Specialist Key Responsibilities This position exists to enable new schools to be onboarded, invoiced, and managed at scale via automated, dependable, repeatable operations and reporting systems.

Basic Requirements

• Capability to work full-time remotely with a minimum of 6 hours overlap with US business hours on weekdays
• Background managing client, customer, or partner onboarding processes across multiple stages and platforms
• Background producing invoices and overseeing billing and accounts receivable workflows
• Background creating automated reports or data pipelines using spreadsheets, scripting, and/or analytics platforms
• Proven active application of AI tools to automate or expedite operational tasks
• Proficient written communication abilities for liaising with external partners and internal teams

Nice-to-have Requirements

• Background using HubSpot, NetSuite, and/or Stripe in an operations, billing, or reporting role
• Background connecting data across systems (CRM, SIS, billing) to generate operational dashboards
• Familiarity coordinating testing setup processes (MAP/NWEA) as part of school or program onboarding

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 $50 USD/hour, which equates to $100,000 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-5756-US-COUNTRY-TechnicalOpera.002