Cartwheel

Director, Strategic Finance

Cartwheel

full-time

Posted on:

Origin:  • 🇺🇸 United States

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Salary

💰 $175,000 - $225,000 per year

Job Level

Lead

About the role

  • Build the Strategic Finance function at Cartwheel from the ground up
  • Improve and maintain Cartwheel’s financial/operating forecast, in close partnership with the COO, CEO, and leadership team. This includes scenario planning to drive investment decisions.
  • Monitor and report on key financial metrics aligned to our OKRs to the Senior Leadership Team and Board of Directors.
  • Partner with departments to strategically manage their budgets and analyze variance
  • Collaborate with outsourced accounting partners to ensure timely and accurate monthly close; work toward insourcing accounting function, including hiring a controller in early 2026
  • Partner cross-functionally to drive effective decision-making across the business. You will be working most closely with the People and Operations teams but will also engage with Sales, Customer Success, R&D, and others as well. This includes creating important analyses to inform key decisions (e.g., school district-level profitability, state-level contribution margin).

Requirements

  • You have led strategic finance functions in a business relevant to Cartwheel (e.g., B2B2C go to market motion, state-by-state market rollout, regulated industry)
  • You have relevant PE, banking, or consulting experience, including strong financial modeling skills
  • You are a highly analytical thinker and enjoy working in a culture that values structured logical reasoning (for example, you naturally think in a MECE Framework)
  • You are highly accountable (e.g., you define clear outcomes, set deadlines, escalate risks, deliver)
  • You are obsessive and will seek to understand our business down to the last dollar. You see this level of detail-orientation as core to your role and not something to delegate or outsource.
  • You embody our values: Human, Humble, Accountable, Innovative, Resilient