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

Elite Finance Architects Only: Build the AI-Native Financial Infrastructure Powering Education's FutureYou've mastered traditional finance leadership. Now engineer the system that makes it obsolete.At Trilogy, we're building revolutionary education businesses that require equally revolutionary financial infrastructure. This isn't about maintaining the status quo—it's about architecting AI-native financial systems that scale effortlessly across multiple education ventures without the bloat of traditional finance departments.Working directly with senior leadership, you'll design the financial backbone supporting bold new school models that will transform how millions learn. You won't just manage finances—you'll engineer the infrastructure that makes traditional finance teams unnecessary.

What You Will Be Doing

• Architecting and implementing an AI-first finance ecosystem that scales across multiple high-growth education businesses
• Authoring critical Design Decisions that systematize and streamline complex financial workflows
• Delivering precise written feedback on Deep Dives and Improvement Plans to train both AI systems and human operators
• Participating in strategic meetings focused on budgets, expansion planning, vendor negotiations, and compliance requirements
• Ensuring seamless execution of core financial operations—tuition management, audits, tax filings—at scale
  

What You Won’t Be Doing

• Overseeing a conventional finance department with layers of specialists
• Spending hours on routine monthly close processes or manual transaction approvals
• Settling for off-the-shelf ERP solutions without significant customization
• Directing from a distance—this role requires hands-on system building
• Operating in a predictable, stable environment—we're in rapid build-scale-iterate mode
  

Chief Financial Officer Key Responsibilities

Architect and operate a lean, AI-native finance system that powers multiple high-growth education businesses, with zero bloat and maximum scale.

Basic Requirements

• CPA, ACA, ACCA, CIMA, CFA, or MBA
• 10+ years in progressive finance leadership positions with demonstrated scope expansion
• Senior finance leadership experience (SVP, CFO, or equivalent) with comprehensive ownership of core finance functions
• Expert-level command of US GAAP and integrated financial reporting
• Extensive experience optimizing ERP systems (NetSuite, SAP, etc.) in complex, multi-entity environments
• Successfully led or managed 5+ external audits with Big 4 firms
• Exceptional written and verbal English communication skills for direct executive engagement
• Located within UTC-8 to UTC+3 time zones
  

Nice-to-have Requirements

• Knowledge of U.S. K-12 education models (private, charter, ESA programs)
• Proven track record building finance automation or AI-driven workflows from the ground up
• Experience navigating finance 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-IN-Mumbai-ChiefFinancial.041