Crossover
Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year US
Crossover, Chicago, Illinois, United States, 60290
Director of Operations & Automation, 2 Hour Learning (Remote)
$100.00/h
($200,000/year). Offered through Crossover as a contractor.
Base Pay Range $100.00/h – $100.00/h
Operations isn’t a support function here—it’s the backbone of everything we do.
Authorization & Permitting – obtain multi‑state legal clearance and expedite local permits to open new markets.
Physical Build‑Out & Maintenance – manage campus construction, facility improvements, and vendor accountability.
IT Operational Setup – ensure every new campus launches with full system readiness—hardware, software, support infrastructure, and compliance—on day one.
Financial Operations – create budgets, generate real‑time insight dashboards, and ensure audit‑grade financial oversight across all schools and business units.
PMO – drive execution of critical technology and marketing projects through vendor performance tracking, reporting dashboards, and initiative management.
You’ll build dashboards that eliminate financial opacity, create onboarding frameworks that cut student setup failures in half, obtain state regulatory clearance, launch campuses faster than anyone thought possible, or develop AI‑native operating models that eliminate entire layers of traditional oversight.
What You Will Be Doing
Leading one of five foundational operations domains: Authorization, Build‑Out, Platforms, Finance, or PMO.
Addressing novel challenges in your domain through AI, automation, and fast experimentation.
Creating clear documentation, dashboards, or process guides that work at multi‑campus scale.
Engaging with operational realities: facility vendors, regulatory bodies, technical systems, and campus teams.
Visiting school sites when necessary to deploy or validate your operational solutions.
What You Won’t Be Doing
Waiting for product or engineering teams to build operational tools—you’ll prototype and automate independently.
Asking AI to “generate a standard operating procedure” and considering the work finished—you’ll vibe‑code functional solutions.
Operating exclusively from headquarters—expect regular travel and on‑campus delivery.
Delegating execution of your strategy to others—you’ll own both planning and implementation.
Key Responsibilities Deliver results within your designated operations pillar by creating scalable systems that enable rapid school expansion with precision, efficiency, and AI‑first methodology.
Basic Requirements
Located in North America with flexibility to travel 25‑75% as required.
5+ years in a high‑velocity, high‑autonomy operations environment.
Excellent analytical capabilities and written communication.
Action‑oriented mindset, minimal ego, strong sense of ownership.
Background in regulatory compliance, facilities construction, SaaS user onboarding, FP&A, or technology vendor management.
Leverages AI with the same fluency others apply to spreadsheets: reflexively, often, and across diverse scenarios.
Has created automations, systematized processes, and explored vibe‑coding for productivity or personal interest.
Demonstrated ability to master new domains quickly (legal, finance, compliance, systems, etc.).
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.
Working with Us This is a full‑time (40 hours per week), long‑term position available immediately. The position 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.
#J-18808-Ljbffr
($200,000/year). Offered through Crossover as a contractor.
Base Pay Range $100.00/h – $100.00/h
Operations isn’t a support function here—it’s the backbone of everything we do.
Authorization & Permitting – obtain multi‑state legal clearance and expedite local permits to open new markets.
Physical Build‑Out & Maintenance – manage campus construction, facility improvements, and vendor accountability.
IT Operational Setup – ensure every new campus launches with full system readiness—hardware, software, support infrastructure, and compliance—on day one.
Financial Operations – create budgets, generate real‑time insight dashboards, and ensure audit‑grade financial oversight across all schools and business units.
PMO – drive execution of critical technology and marketing projects through vendor performance tracking, reporting dashboards, and initiative management.
You’ll build dashboards that eliminate financial opacity, create onboarding frameworks that cut student setup failures in half, obtain state regulatory clearance, launch campuses faster than anyone thought possible, or develop AI‑native operating models that eliminate entire layers of traditional oversight.
What You Will Be Doing
Leading one of five foundational operations domains: Authorization, Build‑Out, Platforms, Finance, or PMO.
Addressing novel challenges in your domain through AI, automation, and fast experimentation.
Creating clear documentation, dashboards, or process guides that work at multi‑campus scale.
Engaging with operational realities: facility vendors, regulatory bodies, technical systems, and campus teams.
Visiting school sites when necessary to deploy or validate your operational solutions.
What You Won’t Be Doing
Waiting for product or engineering teams to build operational tools—you’ll prototype and automate independently.
Asking AI to “generate a standard operating procedure” and considering the work finished—you’ll vibe‑code functional solutions.
Operating exclusively from headquarters—expect regular travel and on‑campus delivery.
Delegating execution of your strategy to others—you’ll own both planning and implementation.
Key Responsibilities Deliver results within your designated operations pillar by creating scalable systems that enable rapid school expansion with precision, efficiency, and AI‑first methodology.
Basic Requirements
Located in North America with flexibility to travel 25‑75% as required.
5+ years in a high‑velocity, high‑autonomy operations environment.
Excellent analytical capabilities and written communication.
Action‑oriented mindset, minimal ego, strong sense of ownership.
Background in regulatory compliance, facilities construction, SaaS user onboarding, FP&A, or technology vendor management.
Leverages AI with the same fluency others apply to spreadsheets: reflexively, often, and across diverse scenarios.
Has created automations, systematized processes, and explored vibe‑coding for productivity or personal interest.
Demonstrated ability to master new domains quickly (legal, finance, compliance, systems, etc.).
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.
Working with Us This is a full‑time (40 hours per week), long‑term position available immediately. The position 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.
#J-18808-Ljbffr