Trilogy
Program Director, 2 Hour Learning (Remote) - $400,000/year USD
Trilogy, Nashville, Tennessee, United States, 37247
Overview
Ready to transform from portfolio manager to portfolio architect? At 2 Hour Learning, we're redefining learning progress with an AI-accelerated platform. We need a strategic orchestrator to build the execution framework powering this transformation. This role manages a $50M EdTech portfolio, with dashboards replacing meetings, and vendor performance driving resource allocation, all tied to student success. If you’re ready to move beyond presentations and wield real decision-making authority with vendors, tools, and execution strategies that drive educational breakthroughs, this is your opportunity to make an impact at the speed of innovation. What You Will Be Doing
Architecting and maintaining an AI-enhanced execution dashboard ecosystem that provides real-time visibility across 25+ concurrent initiatives Developing data-driven vendor evaluation frameworks that trigger decisive action—from expanded partnerships to contract termination Spearheading competitive selection processes for new initiatives with clear parameters, budget frameworks, and decision criteria Crafting contracts with performance metrics, accountability mechanisms, and financial safeguards Authoring executive-level decision documents that identify vendor performance gaps, reference contractual obligations, and recommend specific interventions What You Won’t Be Doing
Serving as a passive coordinator—your role carries decision-making authority, not just administrative responsibility Waiting for problems to become crises—you'll identify issues early, intervene decisively, and drive resolution Tolerating vague deliverables, missed deadlines, or financial uncertainty in vendor relationships Creating status updates without corresponding action plans Outsourcing AI integration—you'll personally leverage AI tools to enhance program effectiveness Program Director Key Responsibilities
Design, implement, and operate a comprehensive execution framework that ensures vendor accountability, optimizes resource allocation, and guarantees timely, high-quality deliverables across our $50M educational technology portfolio. Basic Requirements
Minimum 5 years' experience in senior Program Management, Portfolio Management, or PMO leadership overseeing multifaceted initiative portfolios Demonstrated management of $25M+ technology investments, including vendor selection, budget stewardship, and delivery accountability Substantial expertise in managing competitive bidding processes and negotiating performance-based contracts Track record of creating and maintaining AI-enhanced execution platforms (Linear, Jira, Notion) that inform executive decision-making—beyond basic progress tracking Proficient daily application of AI solutions (GPT, Copilot, analytics dashboards) to streamline workflows, extract insights, and expedite deliverables Demonstrated success driving outcomes in uncharted territory—resolving complex challenges, elevating critical issues, and taking ownership in ambiguous, high-pressure environments Exceptional executive communication capabilities, with proven success influencing C-suite decisions through strategic documentation, visual analytics, and vendor management Based in the US, willing to travel domestically up to 25%, and authorized to work in the US without sponsorship Nice-to-have Requirements
Previous leadership in establishing or transforming a PMO or operational control framework Knowledge of educational technology ecosystems or academic performance metrics Background in legal aspects, procurement processes, or contract management within technology sectors 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. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can fix a broken school system. 2 Hour Learning is reprogramming learning for the AI era. 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-5564-US-Nashville-ProgramDirector.003 Location and Seniority
Seniority level: Executive Employment type: Full-time Job function: Business Development, Engineering, and Project Management Industries: Education Administration Programs, Higher Education, and Non-profit Organizations Referrals increase your chances of interviewing at Trilogy. Get notified about new Director of Learning jobs in Nashville, TN.
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Ready to transform from portfolio manager to portfolio architect? At 2 Hour Learning, we're redefining learning progress with an AI-accelerated platform. We need a strategic orchestrator to build the execution framework powering this transformation. This role manages a $50M EdTech portfolio, with dashboards replacing meetings, and vendor performance driving resource allocation, all tied to student success. If you’re ready to move beyond presentations and wield real decision-making authority with vendors, tools, and execution strategies that drive educational breakthroughs, this is your opportunity to make an impact at the speed of innovation. What You Will Be Doing
Architecting and maintaining an AI-enhanced execution dashboard ecosystem that provides real-time visibility across 25+ concurrent initiatives Developing data-driven vendor evaluation frameworks that trigger decisive action—from expanded partnerships to contract termination Spearheading competitive selection processes for new initiatives with clear parameters, budget frameworks, and decision criteria Crafting contracts with performance metrics, accountability mechanisms, and financial safeguards Authoring executive-level decision documents that identify vendor performance gaps, reference contractual obligations, and recommend specific interventions What You Won’t Be Doing
Serving as a passive coordinator—your role carries decision-making authority, not just administrative responsibility Waiting for problems to become crises—you'll identify issues early, intervene decisively, and drive resolution Tolerating vague deliverables, missed deadlines, or financial uncertainty in vendor relationships Creating status updates without corresponding action plans Outsourcing AI integration—you'll personally leverage AI tools to enhance program effectiveness Program Director Key Responsibilities
Design, implement, and operate a comprehensive execution framework that ensures vendor accountability, optimizes resource allocation, and guarantees timely, high-quality deliverables across our $50M educational technology portfolio. Basic Requirements
Minimum 5 years' experience in senior Program Management, Portfolio Management, or PMO leadership overseeing multifaceted initiative portfolios Demonstrated management of $25M+ technology investments, including vendor selection, budget stewardship, and delivery accountability Substantial expertise in managing competitive bidding processes and negotiating performance-based contracts Track record of creating and maintaining AI-enhanced execution platforms (Linear, Jira, Notion) that inform executive decision-making—beyond basic progress tracking Proficient daily application of AI solutions (GPT, Copilot, analytics dashboards) to streamline workflows, extract insights, and expedite deliverables Demonstrated success driving outcomes in uncharted territory—resolving complex challenges, elevating critical issues, and taking ownership in ambiguous, high-pressure environments Exceptional executive communication capabilities, with proven success influencing C-suite decisions through strategic documentation, visual analytics, and vendor management Based in the US, willing to travel domestically up to 25%, and authorized to work in the US without sponsorship Nice-to-have Requirements
Previous leadership in establishing or transforming a PMO or operational control framework Knowledge of educational technology ecosystems or academic performance metrics Background in legal aspects, procurement processes, or contract management within technology sectors 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. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can fix a broken school system. 2 Hour Learning is reprogramming learning for the AI era. 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-5564-US-Nashville-ProgramDirector.003 Location and Seniority
Seniority level: Executive Employment type: Full-time Job function: Business Development, Engineering, and Project Management Industries: Education Administration Programs, Higher Education, and Non-profit Organizations Referrals increase your chances of interviewing at Trilogy. Get notified about new Director of Learning jobs in Nashville, TN.
#J-18808-Ljbffr