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Director of Strategic Finance, Learning; Remote

Remote / Online - Candidates ideally in
Tampa, Hillsborough County, Florida, 33646, USA
Listing for: Crossover
Part Time, Remote/Work from Home position
Listed on 2026-03-01
Job specializations:
  • Finance & Banking
    Financial Consultant, Corporate Finance, Financial Analyst
Salary/Wage Range or Industry Benchmark: 200000 USD Yearly USD 200000.00 YEAR
Job Description & How to Apply Below
Position: Director of Strategic Finance, 2 Hour Learning (Remote) - $200,000/year USD

Overview

This is not traditional FP&A. It's financial operations designed for people who build. 2 Hour Learning is creating a school network that functions on a different model. We operate with speed, make decisions every day, and require financial transparency that can match our pace. You won't spend time analyzing outdated budgets or depending on business intelligence teams. Instead, you'll create the models, dashboards, and controls that provide operators and leadership with the clarity required to make informed decisions – every day.

Your contributions drive outcomes from new school openings to strategic shifts, and they must be rapid, precise, and reliable. You'll be responsible for a live, AI-enhanced finance infrastructure. This includes integrated profit and loss models for every school and business unit. Continuous 12–18 month projections that remain current within 72 hours. Dashboards that highlight the two or three drivers that truly matter.

You'll leverage AI tools such as ChatGPT and Copilot to speed up your analysis and remove operational friction. You're not developing systems from the ground up—you're applying available tools to complete work more efficiently.

This role isn't suited for operations managers who thrive in structured hierarchies. It's for finance professionals tired of bureaucracy and sluggish workflows. You employ AI tools to increase velocity and expect your models to inform execution rather than simply document the past. You won't be waiting on the periphery for approval. You'll be integral to how we advance.

What You Will Be Doing
  • Create and maintain dynamic 3-statement financial models for every school and vertical, integrating enrollment, staffing, and capital expenditure into unified forecasts.
  • Refresh rolling 12–18 month projections weekly with current data and perform scenario testing for upside and downside risk.
  • Produce executive dashboards powered by real-time data, surfacing critical levers and supporting confident decision-making on a daily basis.
  • Leverage AI tools to speed up analysis, identify anomalies, monitor variances, and remove spreadsheet inefficiencies throughout finance operations.
  • Draft concise memos summarizing financial risk, strategic alternatives, and budget impacts at a board-ready standard, delivered within 72 hours.
What You Won’t Be Doing
  • Running slow budget cycles or generating reports that go unused — your forecasts adapt with the business in real time, and your outputs inform decisions within days.
  • Enforcing cost center compliance or tracking down receipts — you'll prioritize clarity and oversight, not red tape.
  • Relying on BI teams — you create the tools, dashboards, and models independently.
  • Getting lost in irrelevant details — your role is to isolate the few insights that shift outcomes.
  • Developing automated systems from the ground up — you'll apply AI tools to enhance your productivity, not build technical infrastructure.
Director Of Strategic Finance

Key Responsibilities

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

Basic 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 Requirements
  • CPA/CFA/MBA certification
  • ERP experience in Net Suite, 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
About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down…

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