Director, Strategic Finance

Cartwheel

full-time

Posted on: 9/6/2025

Location: 🇺🇸 United States

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💰 $175,000 - $225,000 per year

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).

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