Crossover
Head of AI Operations, 2 Hour Learning (Remote) - $200,000/year USD
Crossover, Orlando, Florida, us, 32885
Head of AI Operations, 2 Hour Learning (Remote) – $200,000 /year USD
Crossover
invites candidates to apply for the Head of AI Operations role (2 Hour Learning). The position is fully remote, full‑time, and pays $100 USD/hour ($200,000 USD/year assuming 40 hrs per week). Base pay range
$100.00/hr – $100.00/hr Operations here is not a support function—it is the product itself. 2 Hour Learning runs a national network of AI‑native K‑12 schools. Success depends on campus systems that scale reliably. Our Operations Team leads expansion, not supports it from the sidelines. Every team member specializes in one of five mission‑critical domains, building deep expertise through hands‑on execution and AI‑powered learning. Mission‑critical domains
Authorization & Permitting – Navigate multi‑state legal frameworks and accelerate local permits to open new markets. Physical Build‑Out & Maintenance – Manage campus construction, facility upgrades, and vendor accountability to deliver and maintain exceptional environments. IT Operational Setup – Deploy complete systems at every new school—hardware, platforms, support infrastructure, compliance—configured and operational from day one. Financial Operations – Create budgets, generate real‑time insight dashboards, and ensure audit‑ready financial integrity across all schools and business units. PMO – Drive execution of strategic technology and marketing projects through vendor performance tracking, dashboards, and initiative reporting. You will build dashboards that expose hidden financial risks, architect onboarding workflows that cut student setup failures in half, win regulatory clearance in unfamiliar states, launch campuses on compressed timelines, and develop AI‑native processes that eliminate traditional management overhead. This is high‑stakes, high‑speed execution carried out by operators, not observers. What You Will Be Doing
Taking ownership of one of five operational pillars: Authorization, Build‑Out, Platforms, Finance, or PMO. Addressing novel challenges in your domain through AI tools, automation, and iterative testing. Creating detailed specifications, dashboards, or operating guides that function across multiple school sites. Engaging directly with operational realities: facility contractors, regulatory bodies, technology stacks, and campus personnel. Visiting school locations as required to deploy or validate your systems in live environments. What You Won’t Be Doing
Relying on product or engineering teams to create your operational tools—you will build or automate them directly. Prompting AI to generate documentation and treating that as finished work—you will develop functional solutions through hands‑on iteration. Operating exclusively from a central office—anticipate regular travel and on‑the‑ground delivery. Delegating execution of your strategy to others—you will own both planning and implementation completely. Head Of AI Operations Key Responsibilities
Take full ownership of outcomes in your designated operations pillar by designing and implementing systems that enable rapid, accurate, AI‑powered school expansion at scale. Basic Requirements
Located in North America with flexibility to travel 25‑75% depending on operational needs. Minimum 5 years in a high‑tempo, autonomous operations environment. Excellent analytical thinking and written communication capabilities. Action‑oriented mindset, minimal ego, strong sense of ownership. Background in at least one of: regulatory compliance, facilities construction, SaaS onboarding, FP&A, or technology vendor oversight. Applies AI as naturally as others use spreadsheets: reflexively, regularly, and across diverse scenarios. Has created workflow automations, systematized processes, and explored vibe‑coding for personal productivity or problem‑solving. Demonstrated ability to quickly master unfamiliar domains (legal frameworks, financial systems, compliance structures, technical platforms, 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 hrs 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. The compensation level is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hrs per week and 50 weeks per year. Payment is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5461-US-Orlando-HeadofAIOperat.006. Seniorities and Employment
Seniority level: Director Employment type: Full‑time Job function: Engineering and Information Technology Industries: Software Development, Education Administration Programs, IT Services, IT Consulting
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Crossover
invites candidates to apply for the Head of AI Operations role (2 Hour Learning). The position is fully remote, full‑time, and pays $100 USD/hour ($200,000 USD/year assuming 40 hrs per week). Base pay range
$100.00/hr – $100.00/hr Operations here is not a support function—it is the product itself. 2 Hour Learning runs a national network of AI‑native K‑12 schools. Success depends on campus systems that scale reliably. Our Operations Team leads expansion, not supports it from the sidelines. Every team member specializes in one of five mission‑critical domains, building deep expertise through hands‑on execution and AI‑powered learning. Mission‑critical domains
Authorization & Permitting – Navigate multi‑state legal frameworks and accelerate local permits to open new markets. Physical Build‑Out & Maintenance – Manage campus construction, facility upgrades, and vendor accountability to deliver and maintain exceptional environments. IT Operational Setup – Deploy complete systems at every new school—hardware, platforms, support infrastructure, compliance—configured and operational from day one. Financial Operations – Create budgets, generate real‑time insight dashboards, and ensure audit‑ready financial integrity across all schools and business units. PMO – Drive execution of strategic technology and marketing projects through vendor performance tracking, dashboards, and initiative reporting. You will build dashboards that expose hidden financial risks, architect onboarding workflows that cut student setup failures in half, win regulatory clearance in unfamiliar states, launch campuses on compressed timelines, and develop AI‑native processes that eliminate traditional management overhead. This is high‑stakes, high‑speed execution carried out by operators, not observers. What You Will Be Doing
Taking ownership of one of five operational pillars: Authorization, Build‑Out, Platforms, Finance, or PMO. Addressing novel challenges in your domain through AI tools, automation, and iterative testing. Creating detailed specifications, dashboards, or operating guides that function across multiple school sites. Engaging directly with operational realities: facility contractors, regulatory bodies, technology stacks, and campus personnel. Visiting school locations as required to deploy or validate your systems in live environments. What You Won’t Be Doing
Relying on product or engineering teams to create your operational tools—you will build or automate them directly. Prompting AI to generate documentation and treating that as finished work—you will develop functional solutions through hands‑on iteration. Operating exclusively from a central office—anticipate regular travel and on‑the‑ground delivery. Delegating execution of your strategy to others—you will own both planning and implementation completely. Head Of AI Operations Key Responsibilities
Take full ownership of outcomes in your designated operations pillar by designing and implementing systems that enable rapid, accurate, AI‑powered school expansion at scale. Basic Requirements
Located in North America with flexibility to travel 25‑75% depending on operational needs. Minimum 5 years in a high‑tempo, autonomous operations environment. Excellent analytical thinking and written communication capabilities. Action‑oriented mindset, minimal ego, strong sense of ownership. Background in at least one of: regulatory compliance, facilities construction, SaaS onboarding, FP&A, or technology vendor oversight. Applies AI as naturally as others use spreadsheets: reflexively, regularly, and across diverse scenarios. Has created workflow automations, systematized processes, and explored vibe‑coding for personal productivity or problem‑solving. Demonstrated ability to quickly master unfamiliar domains (legal frameworks, financial systems, compliance structures, technical platforms, 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 hrs 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. The compensation level is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hrs per week and 50 weeks per year. Payment is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5461-US-Orlando-HeadofAIOperat.006. Seniorities and Employment
Seniority level: Director Employment type: Full‑time Job function: Engineering and Information Technology Industries: Software Development, Education Administration Programs, IT Services, IT Consulting
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