Director of Strategic Finance, 2 Hour Learning (Remote) - $200,000/year USD at Trilogy

Reimagine Financial Leadership: Where Strategy Meets Execution

At 2 Hour Learning, finance isn't a back-office function—it's the engine that powers our growth. As Director of Strategic Finance, you'll craft the financial narrative that drives our network of schools forward. Forget static spreadsheets and quarterly reviews. Your dynamic models and real-time dashboards will inform decisions happening today, tomorrow, and next quarter.

You'll architect an AI-enhanced financial ecosystem where P&L models breathe with the rhythm of our business, forecasts stay remarkably current, and dashboards instantly reveal the critical few metrics that matter. Using cutting-edge tools like Klair, Syft, and Retool, you'll build financial infrastructure that operates at the speed of our ambition—no technical dependencies required.

This role places you at the strategic heart of our organization. Your financial insights won't gather dust—they'll catalyze action and shape our trajectory in real-time.

What You Will Be Doing

• Architect comprehensive 3-statement financial models for each educational vertical, creating a financial digital twin that connects enrollment patterns, staffing requirements, and capital investments.
• Maintain continuously evolving 12-18 month forecasts with weekly refreshes, stress-testing various scenarios to anticipate both opportunities and challenges.
• Design executive intelligence dashboards powered by live data streams that illuminate critical decision points and enable confident, rapid strategic pivots.
• Leverage AI and automation to create a self-monitoring financial system that flags anomalies, tracks performance variances, and eliminates manual data processing bottlenecks.
• Craft concise, insightful financial narratives that distill complex situations into board-ready recommendations within 72-hour turnaround windows.
  
  

What You Won’t Be Doing

• Orchestrating cumbersome annual budget cycles—your financial frameworks evolve continuously alongside business realities.
• Implementing bureaucratic expense controls—you'll focus on meaningful financial governance, not administrative overhead.
• Submitting data requests to technical teams—you'll independently build and maintain the analytical tools you need.
• Processing excessive data without insight—your expertise will filter signal from noise to highlight truly impactful metrics.
• Creating ceremonial reports—your deliverables will directly influence operational decisions within days of completion.
  
  

Director Of Strategic Finance Key Responsibilities

Serve as the financial cornerstone of our educational network by delivering perpetually current models, forecasts, and visual analytics that empower both day-to-day operational decisions and long-term strategic planning across our rapidly expanding portfolio of schools.

Basic Requirements

• Bachelor's degree in Accounting, Finance, Economics, or Mathematics (CPA/CFA certification or MBA viewed favorably)
• U.S. residency with authorization to work without visa sponsorship
• Ability to commit to approximately 25% travel to campus locations throughout the United States
• 3-6 years of professional experience in investment banking, private equity, Big 4 corporate finance/M&A divisions (excluding audit), or high-growth FP&A roles
• Demonstrated proficiency creating sophisticated 3-statement financial models aligned with U.S. GAAP standards
• Proven ability to deliver investment-quality analysis and strategic recommendations under compressed timeframes
• Active proficiency with AI-enhanced productivity tools (such as GPT, Klair, Syft, Retool, and NetSuite automation capabilities)
  
  

Nice-to-have Requirements

• Hands-on experience with enterprise resource planning systems, particularly NetSuite, Oracle, or SAP
• Background in multi-location education, facilities management, or operations-intensive business sectors
• Track record preparing board presentations or investor-facing financial materials
• Demonstrated success implementing AI-powered financial dashboards or developing low-code finance applications
• Previous work in premium service environments with stringent financial performance standards
  
  

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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5680-US-SandySpr-DirectorofStra