Group Finance Director, Trilogy (Remote) - $400,000/year USD

What if you could revolutionize financial operations by making humans optional? Welcome to the future of educational finance, where AI meets ambition.

We're not just looking for a Group Finance Director – we're seeking a visionary architect who can transform traditional finance into an AI-powered masterpiece. At Trilogy, we're building an education empire, and we need someone who can create a financial ecosystem that runs like a Swiss watch – precise, reliable, and remarkably autonomous.

If you're the kind of financial expert who sees spreadsheets as sculptures waiting to be carved, and manual processes as opportunities for automation, you're speaking our language. This isn't about maintaining the status quo – it's about demolishing it and building something extraordinary in its place.

Think of this as your chance to write the playbook for how billion-dollar education ventures should operate financially in the AI age. No bureaucracy, no unnecessary headcount, just pure, elegant efficiency.

Are you ready to turn financial operations into a symphony of automation? Your canvas awaits.

What You Will Be Doing

• Orchestrate a revolution in financial processes by weaponizing AI to eliminate human intervention in billing, reporting, and compliance
• Transform NetSuite, Ramp, and other systems into a seamless, AI-enhanced ecosystem that runs on autopilot
• Design and implement bulletproof systems for handling tuition, ESA payments, and tax documentation that scale effortlessly
• Create a financial reporting infrastructure so robust it can handle multiple education ventures without breaking a sweat
• Engineer financial systems that laugh in the face of traditional scaling limitations, supporting billion-dollar operations without bloating the team
  
  

What You Won’t Be Doing

• Playing traditional finance director – we're not building an army of accountants
• Getting bogged down in routine month-end procedures or transaction approvals
• Accepting mediocrity in any form – if a process can be automated, it will be
• Managing from the sidelines – you'll be in the trenches, leading the automation charge
• Maintaining the status quo – we're building for hypergrowth, not steady-state operations
  
  

Group Finance Director Key Responsibilities

Build and deploy an AI-powered financial ecosystem capable of autonomously managing multiple billion-dollar education ventures with zero human intervention required.

Basic Requirements

• Professional certification in finance (CPA, ACA, ACCA, CIMA, CFA, or MBA)
• Battle-tested experience in $100M+ business finance operations
• Deep understanding of audit processes (either 5+ years at a top 10 firm or equivalent experience being audited)
• Mastery of enterprise ERP systems like NetSuite or SAP
• Proven track record of leveraging generative AI tools in professional finance settings
• Your time zone must fall between UTC-8 and UTC+3
  
  

Nice-to-have Requirements

• Inside knowledge of U.S. K-12 education landscape (private, charter, ESA programs)
• Track record of building AI-enhanced finance automation systems
• Experience navigating complex multi-entity, multi-jurisdiction financial environments
  
  

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.012