Trilogy

Compensation

Full Description

Forget traditional program management. This is your chance to architect the backbone of an educational revolution. At 2 Hour Learning, we're achieving the impossible: students learn twice as much in just 120 minutes daily. Powering this breakthrough is a sophisticated $50M EdTech ecosystem that needs your strategic orchestration. We're seeking a visionary to design and implement the operating framework that drives our portfolio to peak performance. You'll craft the infrastructure that brings crystal-clear visibility, unwavering accountability, and accelerated progress across 25+ transformative initiatives. Your systems won't just track completion—they'll validate if we're investing in solutions that deliver measurable learning outcomes. From establishing performance benchmarks to implementing AI-powered analytics, from enforcing competitive vendor selection to creating real-time dashboards that reveal ground truth, your influence will extend from execution to strategy. Working directly with our founders, you'll transform ambitious vision into methodical action. If you excel in complex environments, value autonomy, and are driven by meaningful impact, this role was designed for you. What You Will Be Doing • Establishing an AI-enhanced Program Management Office that synchronizes and optimizes 25+ educational technology initiatives across our $50M portfolio • Developing and implementing a comprehensive vendor evaluation framework to reallocate resources based on quantifiable performance metrics • Architecting and enforcing a rigorous competitive bidding process for all new projects to maximize return on investment • Deploying cutting-edge tracking systems (e.g., Linear) to deliver executive-level transparency and actionable insights • Orchestrating seamless alignment between internal teams and external partners on deliverables, documentation standards, and educational outcomes What You Won’t Be Doing • Manually compiling status updates and spreadsheets; you'll leverage technology to automate routine reporting • Endlessly negotiating with underdelivering vendors; your framework provides clear performance standards and consequences • Participating in information-gathering meetings; your systems will provide real-time visibility before discussions begin • Running a compliance-focused PMO; your operation will prioritize measurable learning outcomes above all • Working with ambiguous success metrics; you'll implement AI-driven analytics to quantify educational impact, not just project completion Director Of Program Management Key Responsibilities Design and spearhead a next-generation, AI-enhanced Program Management Office that transforms our $50M EdTech investment portfolio into quantifiable academic achievements with unprecedented efficiency. Basic Requirements • Proven 10+ year track record in Program/Portfolio Management or PMO Leadership, successfully orchestrating complex, multi-initiative portfolios • Demonstrated experience managing technology budgets exceeding $25M, with evidence of strategic resource allocation and measurable returns • Advanced proficiency in vendor ecosystem management, including competitive procurement processes, contract negotiations, and performance optimization • Successful implementation of centralized project tracking platforms, preferably with AI capabilities (Linear, Jira, Asana, or comparable systems) • Exceptional executive communication skills, with demonstrated ability to influence C-level strategic decisions • Practical experience leveraging artificial intelligence for workflow automation and data analytics to drive operational excellence • North America-based candidates only 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 $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-Dallas-DirectorofProg