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Director of Retail Operations, 2 Hour Learning (Remote) - $400,000/year USD

Trilogy
Portland, OR Remote Full Time
POSTED ON 8/5/2025 CLOSED ON 9/5/2025

What are the responsibilities and job description for the Director of Retail Operations, 2 Hour Learning (Remote) - $400,000/year USD position at Trilogy?

ARCHITECT THE FUTURE OF EDUCATION: SVP OPERATIONS

2 Hour Learning is launching 25–30 new school campuses in the next six months. This isn't just expansion—it's a revolution in education requiring masterful execution across physical infrastructure, regulatory frameworks, and financial models.

We're seeking exceptional operational leaders who build systems that scale, drive results without excuses, and thrive in high-visibility environments where decisions matter. If you've proven yourself in elite consulting and operational leadership, we'll match your expertise to one of our critical tracks: Regulatory, Campus Build-out, Systems & Onboarding, or Financial Operations.

This is where post-consulting careers reach their potential—full ownership, direct founder access, and the mandate to transform American education at scale.

What You Will Be Doing

Depending on your operational track, you will:

  • Architect and execute regulatory strategy across multiple states, securing all approvals needed for rapid expansion
  • Lead end-to-end campus development—from site selection through construction management to opening day readiness
  • Design and implement scalable onboarding systems and operational infrastructure that support exponential growth
  • Build sophisticated financial models and reporting frameworks that drive strategic decisions across our school network

Across all tracks, you'll operate with complete ownership, cross-functional authority, and direct accountability for results. You deliver, period.

What You Won’t Be Doing

  • Following established processes—you'll create the systems and playbooks that define operational excellence
  • Managing incremental improvements—this is transformational work requiring bold, decisive leadership
  • Focusing on a single location or narrow workstream—you'll orchestrate multiple parallel launches with precision
  • Delegating critical decisions—you'll own the hard calls and their outcomes
  • Producing recommendations without implementation—this is execution, not advisory work

Director Of Retail Operations Key Responsibilities

Drive the operational infrastructure that enables 2 Hour Learning's national expansion, ensuring your domain—whether regulatory, campus development, systems, or financial operations—delivers exceptional results on aggressive timelines without compromise.

Basic Requirements

We demand excellence across all operational tracks. You must demonstrate:

  • Experience at a premier strategy consulting firm (MBB or equivalent such as Deloitte S&O, Strategy&, EY-Parthenon, LEK)
  • 10 years leading operations in complex, regulated environments with measurable outcomes
  • Exceptional expertise in at least one critical domain:
    • Navigating multi-jurisdictional regulatory frameworks and approval processes
    • Managing complex physical build-outs with multiple vendors and tight timelines
    • Designing and implementing scalable operational systems with rigorous SLAs
    • Developing sophisticated financial models and reporting structures across multiple entities
  • Proficiency with AI and advanced tools to eliminate friction and accelerate execution
  • U.S. work authorization and willingness to travel approximately 25% of the time
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-4410-US-Portland-DirectorofReta.015

Salary : $400,000

Dean of Enrollment, 2 Hour Learning - $200,000/year USD
Crossover -
Portland, OR

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