Division CFO, Trilogy (Remote) - $400,000/year USD

Imagine architecting a financial system so intelligent, so autonomous, that it powers a billion-dollar education empire with minimal human intervention. This isn't about maintaining spreadsheets—it's about revolutionizing finance itself.

At Trilogy, we're transforming education through our portfolio of schools, cutting-edge EdTech, and innovative curriculum models like 2 Hour Learning. We need a financial visionary who can match our revolutionary pace. Someone who sees finance not as a department, but as an AI-powered engine of precision, automation, and scalability.

This role transcends traditional CFO responsibilities. You'll be hands-on in NetSuite and Ramp, but more importantly, you'll reimagine these tools through the lens of AI advancement. From tuition processing to ESA reimbursements, from tax documentation to audit preparation—your mission is creating systems so efficient they become invisible.

We're seeking someone who doesn't just streamline workflows but eliminates them entirely. Someone who believes that finance teams shouldn't expand with company growth, but should instead leverage AI to maintain lean, powerful operations.

Join us to engineer the financial blueprint for building and scaling billion-dollar education ventures—again and again.

What You Will Be Doing

• Pioneering AI-first financial architectures that eliminate human touchpoints across all finance functions
• Implementing LLM-powered automations that replace error-prone manual tasks in NetSuite, Ramp, and other financial platforms
• Orchestrating frictionless systems for critical revenue streams including tuition collection, ESA payments, tax compliance, and audit preparation
• Developing scalable, audit-ready financial reporting frameworks adaptable across multiple education business verticals
• Constantly reinventing our financial infrastructure to support billion-dollar business units without headcount expansion
  
  

What You Won’t Be Doing

• Overseeing a traditional finance department—your focus is systems architecture, not personnel management
• Micromanaging month-end processes or transaction approvals
• Accepting suboptimal ERP workflows—you'll relentlessly identify and eliminate inefficiencies
• Pushing tedious tasks downstream—you're a hands-on innovator who leads by example
• Maintaining status quo operations—you'll be driving rapid transformation, not steady-state management
  
  

Division CFO Key Responsibilities

Design and implement a fully autonomous, AI-powered financial ecosystem capable of supporting multiple billion-dollar education ventures with zero manual intervention.

Basic Requirements

• Professional financial qualification (CPA, ACA, ACCA, CIMA, CFA, or MBA)
• Proven financial leadership within a $100M+ enterprise
• Either 5+ years experience at a top 10 global audit firm OR have successfully navigated 5+ audits from the client side
• Demonstrated proficiency with enterprise-grade ERP systems (NetSuite, SAP, etc.)
• Practical experience leveraging generative AI tools (ChatGPT, Claude, Gemini) in professional finance applications
• Geographic location within UTC-8 to UTC+3 time zones
  
  

Nice-to-have Requirements

• Understanding of U.S. K-12 education models (private schools, charter schools, ESA programs)
• Track record of developing finance automation or AI-enhanced workflows from concept to implementation
• Experience navigating financial operations across multiple entities and jurisdictions
  
  

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-GB-London-GroupChiefFina.082