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Trilogy

Head of Program Management, 2 Hour Learning (Remote) - $400,000/year USD

Trilogy, Dallas, Texas, United States, 75215

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Overview

Head of Program Management, 2 Hour Learning (Remote) - $400,000/year USD 6 days ago Be among the first 25 applicants This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range: $200.00/hr - $200.00/hr Are you ready to leverage your experience managing $25M+ portfolios to take the reins of something even grander? At 2 Hour Learning, you won\'t just oversee projects; you\'ll revolutionize the way we educate. We\'re on a mission to compress a full school day into just two hours, doubling learning efficiency without compromising quality. As the architect of our AI-driven control system for a $50M EdTech portfolio, you\'ll replace redundant meetings with dynamic dashboards, drive vendor accountability, and ensure every initiative enhances academic impact. If you\'re seeking autonomy and the chance to truly innovate, this is your moment. Responsibilities

Spearhead a cutting-edge, AI-enhanced execution dashboard for over 25 active initiatives, ensuring transparency and accountability. Craft vendor scorecards that prompt decisive actions—expanding, reducing, or replacing work as needed. Define scopes, budgets, and award justifications in vendor evaluations. Lead contract negotiation to ensure clarity and enforceability. Author memos addressing vendor shortcomings, contract breaches, and suggest resolute measures such as offboarding or renegotiation. What You Won’t Be Doing

Not a role for mere coordinators; you will take charge and drive outcomes. You will proactively address, escalate, or rectify vendor issues and avoid vague contracts or missed deadlines. You will not delegate AI tasks to others; you\'ll be directly involved, using AI to drive success. Head Of Program Management – Key Responsibilities

Your primary duty will be to develop and manage the execution system that holds vendors accountable, optimizes resource allocation, and ensures timely, quality delivery across our $50M EdTech portfolio. Basic Requirements

Over 5 years of experience in Program Management, Portfolio Management, or PMO leadership roles, overseeing intricate, multi-initiative portfolios. Experience in managing $25M+ technology expenditures, including vendor selection, budget oversight, and delivery management. Hands-on experience with competitive bidding and contract negotiations. Proficiency in developing and operating AI-driven execution dashboards (e.g., Linear, Jira, Notion) that inform executive decisions. Regular use of AI tools (like GPT, Copilot, dashboards) for work automation, insight generation, and delivery acceleration. Demonstrated ability to drive results without predefined playbooks, with problem-solving, issue escalation, and ownership in uncertain, high-pressure situations. Strong communication skills with a proven ability to influence executive decisions through memos, dashboards, and vendor management. Must be US-based, willing to travel domestically up to 25%, and eligible to work in the US without sponsorship. Nice-to-have Requirements

Experience in launching or revamping a PMO or control system. Understanding of educational technology platforms or academic success metrics. Familiarity with legal, procurement, or contract management in tech settings. 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-HeadofProgramM Seniority level

Executive Employment type

Full-time Job function

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