Chief Financial Officer (REMOTE)

Division CFO, Trilogy (Remote) – $400,000/year USD Join to apply for the Division CFO, Trilogy (Remote) – $400,000/year USD role at Trilogy Division CFO, Trilogy (Remote) – $400,000/year USD Join to apply for the Division CFO, Trilogy (Remote) – $400,000/year USD role at Trilogy You\’ve mastered finance at scale. You\’ve led audits, wrestled with ERPs, and turned chaos into compliance. Now imagine using that expertise to build a finance system so powerful, it can run — and grow — a billion-dollar education empire without you. This is not your average finance gig. You\’ll lead the charge in turning our finance function into an AI-powered engine of automation, scale, and surgical precision. Tuition payments, ESA reimbursements, tax documentation, audits — you\’ll ensure every process is airtight and invisible. If you believe most finance teams are bloated by default, and that AI is the antidote, this is your opportunity to prove it. Ready to engineer the future of finance? Designing AI-first financial processes that eliminate manual touchpoints across billing, reporting, compliance, and controls Building automations and using LLM tools to replace error-prone human tasks in NetSuite, Ramp, and other finance systems Ensuring mission-critical processes like tuition and ESA payments, tax documentation, and audits run seamlessly and at scale Creating audit-ready financials and reporting flows that can scale across multiple education business lines Continuously iterating and re-architecting finance infrastructure to support $1B+ business units without adding headcount Managing a large team of finance staff — this role is about systems, not people Babysitting month-end close cycles or manually approving transactions Accepting existing ERP workflows as \”good enough\” — you\’ll hunt for waste and kill it Division CFO Key Responsibilities Build a fully autonomous, AI-native finance system capable of powering multiple billion-dollar education ventures with zero manual intervention. CPA, ACA, ACCA, CIMA, CFA, or MBA Experience in a finance or accounting role at a $100M+ business Either: 5+ years as an auditor at a top 10 global firm, or audited 5+ times by one NetSuite, SAP) private, charter, ESA programs) Experience building finance automation or AI-driven workflows from scratch Previous exposure to finance operations in multi-entity, multi-jurisdiction businesses Hundreds of software businesses run on the Trilogy Business Platform. Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today\’s modern cloud-based stack. 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 $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. Employment type Full-time Job function Business Development, Finance, and Engineering Industries Accounting, Financial Services, and IT Services and IT Consulting Sign in to set job alerts for “Division Chief Financial Officer” roles. We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI. #