Director of Operations & Automation, 2 Hour Learning (...

Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year USD Join to apply for the Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year USD role at Trilogy Base pay range $100.00/hr - $100.00/hr Welcome message and application prompts have been removed for clarity and relevance. What You Will Be Doing Owning one of six core ops pillars: Authorization, Build-Out, Setup, Finance, or PMO Solving first-time problems in your pillar using AI, automation, and rapid iteration Writing clear specs, dashboards, or runbooks that scale across dozens of schools Interfacing with real-world constraints: campus vendors, regulators, systems, and staff Traveling to campuses when needed to implement or pressure-test your solutions You'll ship dashboards that clarify financial blind spots. Design onboarding systems that halve student setup errors. Secure regulatory approval in new states. Stand up campuses in record time. Or prototype AI-first workflows that replace layers of traditional management. This is high-stakes, high-velocity execution—done by builders, not bystanders. If you're the kind of operator who sees bottlenecks and starts building—you'll thrive here. Your systems will power the next 25–30 schools we open in the next year. Your work will define what great looks like for hundreds of staff and thousands of students. What You Won’t Be Doing Waiting for product or engineering to build your ops tools—you'll prototype or automate yourself Asking AI to "write an SOP" and calling it a day—you'll vibe-code solutions that actually work Being siloed in a central office—expect to travel and ship on-site outcomes Handing off your strategy to someone else to execute—you'll do both, end-to-end Director Of Operations & Automation Key Responsibilities Own outcomes within your assigned operations pillar by building systems that support blitz-scale school expansion with speed, accuracy, and AI-native precision. Basic Requirements Based in North America and able to travel 10–40% as needed 5+ years in a fast-paced, high-autonomy ops role Proven use of AI tools for research, writing, problem-solving, and automation Strong analytical and written communication skills Bias for action, low ego, high ownership Experience in one of the following: permitting, construction, edtech systems, FP&A, or vendor mgmt Familiarity with tools like Klair, Syft, Wrike, Retool, or other low-code stacks Track record of rapid domain ramp-up (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. 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 $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 for more details on this topic. Crossover Job Code: LJ-5461-US-Boston-DirectorofOper1 Seniority level Director Employment type Full-time Job function Information Technology, Engineering, and Product Management Industries Software Development, Education Administration Programs, and IT Services and IT Consulting Referrals increase your chances of interviewing at Trilogy by 2x Sign in to set job alerts for “Director of Operations” roles. #J-18808-Ljbffr

Created: 2025-09-17