Elite Finance Leaders Don't Just Report Numbers—They Architect Systems That Scale

You've mastered traditional finance leadership. Now build something that matters. At Trilogy, we're revolutionizing education through multiple breakthrough businesses—from K-12 schools to EdTech platforms. Each model challenges convention, and each requires financial infrastructure that's as innovative as our educational approach.

This isn't about managing a department. It's about designing the lean, AI-native finance system that makes traditional bloated teams obsolete. You'll own the architecture that powers tuition flows, streamlines audits, and automates tax filings across our education portfolio. Your decisions will directly influence how millions of students experience learning.

What You Will Be Doing

• Architect and implement an AI-first finance system that scales effortlessly with our rapidly growing education ventures
• Author decisive, strategic design documents that eliminate complexity and standardize critical finance workflows
• Deliver precise written feedback on Deep Dives and Improvement Plans that simultaneously trains both AI systems and human operators
• Engage in high-impact leadership discussions on budgeting, market expansion, vendor negotiations, and compliance requirements
• Ensure all finance operations—from tuition management to audits and tax filings—function flawlessly at scale

What You Won’t Be Doing

• Overseeing large teams of finance personnel—we build systems, not headcount
• Micromanaging routine close processes or transaction approvals that should be automated
• Settling for standard ERP configurations when custom solutions deliver superior results
• Directing from a distance—this role requires hands-on system building and optimization
• Operating in a predictable, established environment—we're building and scaling at pace

Group Finance Director Key Responsibilities Design, implement, and operate a lean, AI-native finance infrastructure that powers multiple high-growth education businesses with maximum efficiency and scalability.

Basic Requirements

• Professional finance qualification (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 knowledge of US GAAP and integrated financial reporting
• Extensive experience optimizing ERP systems (NetSuite, SAP, etc.) in complex, multi-entity environments
• Track record of managing 5+ external audits with Big 4 firms, either as the auditor or client
• Exceptional written and verbal English communication skills for direct executive engagement
• Location 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 success building finance automation or AI-driven workflows from inception
• Demonstrated expertise managing 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-CA-Toronto-GroupFinanceDi.019