Director of Strategic Finance
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Not accepting applications on crossover.com at this time.

Description

This role reimagines what strategic finance looks like. It's built for operators, not committees.

2 Hour Learning is constructing a network of schools that run on different principles. We execute quickly, decide constantly, and require financial insight that moves at the same speed. You won't spend time reviewing outdated budgets or depending on BI infrastructure. Instead, you'll design the models, reporting systems, and frameworks that deliver the visibility operators and leadership require to act with confidence—every single day. Your output influences decisions from new school openings to enterprise-level strategy shifts, and it must be rapid, precise, and reliable.

You'll lead a dynamic, AI-enabled finance operation. This includes consolidated P&L modeling across every school and business line. Continuous 12–18 month projections that remain current within 72 hours. Executive dashboards that isolate the handful of metrics that truly drive outcomes. You'll leverage AI platforms such as ChatGPT and Copilot to speed up insight generation and remove friction. You're not engineering infrastructure—you're deploying available technology to deliver results faster.

This position is not suited to finance leaders who value rigid organizational structures. It's designed for strategic finance professionals tired of red tape and delayed cycles. You adopt AI to multiply your output and expect your forecasts to shape execution, not simply report history. You won't observe from the wings waiting for approval. You'll operate at the core of how decisions get made.

What you will be doing

  • Develop and sustain integrated 3-statement financial models for every school and operating segment, linking enrollment trends, headcount planning, and capital investments into unified forecasts.
  • Refresh rolling 12–18 month projections each week with current data and perform scenario analysis on best- and worst-case outcomes.
  • Create executive reporting dashboards powered by real-time data, surfacing critical drivers and supporting daily decision-making with confidence.
  • Apply AI-powered tools to expedite analytical workflows, identify data outliers, monitor budget variances, and remove manual bottlenecks throughout finance operations.
  • Produce concise executive memos summarizing financial exposure, strategic alternatives, and budgetary impact at board presentation quality, delivered within 72 hours.

What you will NOT be doing

  • Running drawn-out budgeting cycles or generating reports that sit unread—your projections adapt alongside the business in real time, and your analysis informs decisions within days.
  • Enforcing expense policies or tracking receipts—you'll concentrate on transparency and control, not administrative overhead.
  • Depending on BI or data teams—you construct your own reporting tools, dashboards, and financial models.
  • Getting lost in excessive detail—your mission is to highlight the critical few insights that shift outcomes.
  • Engineering automation platforms from the ground up—you'll harness AI tools to amplify productivity, not build technical infrastructure.

Key responsibilities

Provide continuously updated financial models, projections, and executive dashboards that enable daily decision-making and strategic visibility across a fast-expanding school network.

Candidate requirements

  • Willing to work at least 3 hours of daily overlap with US business hours (08:00 - 17:00 US EST / UTC-5)
  • 5+ years in investment banking, private equity, Big 4 corp finance/M&A (not audit), or high-growth FP&A
  • Proven experience building integrated 3-statement models tied to U.S. GAAP
  • Comfortable delivering investor-grade analysis and recommendations under tight deadlines
  • Experience using AI tools (e.g., ChatGPT, Copilot, Claude) to accelerate financial analysis, document generation, and data processing

Nice to have

  • CPA/CFA/MBA certification
  • ERP experience in NetSuite, Oracle, or SAP
  • Familiarity with multi-site education, facilities, or ops-heavy industries
  • Experience with board-level reporting or investor-facing materials
  • Experience building AI-automated dashboards or low-code finance tools
  • Exposure to high-end service environments with exacting financial standards

Meet a successful candidate

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Nadia Dan
Nadia  |  Senior Software Engineer
Romania

Your first time will be flawed. Your 100th time will be flawed. But it takes dedication to get to the 1,000th time and become good. The cons...

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