Chief Financial Officer, Trilogy (Remote) - $400,000/year USD

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. At Trilogy, we’re revolutionizing education through a portfolio of schools, EdTech, and breakthrough curriculum models like 2 Hour Learning — and we need an operator who can match that pace of innovation. You’ll lead the charge in turning our finance function into an AI-powered engine of automation, scale, and surgical precision.

This role is about designing a system, not managing a team. You’ll work hands-on inside tools like NetSuite and Ramp — and you’ll identify ways to augment or replace them with smarter, leaner AI solutions. Tuition payments, ESA reimbursements, tax documentation, audits — you’ll ensure every process is airtight and invisible. We’re not looking for someone to “optimize workflows.” We’re looking for someone who deletes them. If you believe most finance teams are bloated by default, and that AI is the antidote, this is your opportunity to prove it.

You won’t just learn how we build $1B businesses — you’ll codify the blueprint. And then scale it, again and again.

Ready to engineer the future of finance? Apply today.

What You Will Be Doing

• 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
  
  

What You Won’t Be Doing

• 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
• Delegating the “dirty work” to junior staff — you lead by doing
• Operating in a steady-state environment — this is rapid scale, not maintenance mode
  
  

Chief Financial Officer Key Responsibilities

Build a fully autonomous, AI-native finance system capable of powering multiple billion-dollar education ventures with zero manual intervention.

Basic Requirements

• 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
• Professional experience with enterprise ERP systems (e.g. NetSuite, SAP)
• Experience using generative AI tools (e.g. ChatGPT, Claude, Gemini) in a professional capacity
• Must be located within UTC-8 to UTC+3 time zones
  
  

Nice-to-have Requirements

• Familiarity with K-12 education models in the U.S. (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
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

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. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-3652-SA-Riyadh-ChiefFinancial.008