Group Finance Director, Trilogy (Remote) - $400,000/year USD - #449735

Picture this: You've conquered the financial summit. You've orchestrated complex audits, tamed unwieldy ERPs, and transformed financial disarray into pristine compliance. Now, what if you could channel that mastery into creating a financial ecosystem so robust and intelligent that it propels a billion-dollar education enterprise forward—even when you're not at the helm?

This isn't your standard financial leadership position. At Trilogy, we're transforming education through our diverse portfolio of schools, cutting-edge EdTech solutions, and innovative learning frameworks like 2 Hour Learning. We need a financial visionary whose innovative spirit matches our ambitious trajectory. Your mission? Transform our finance function into an AI-driven powerhouse of automation, scalability, and pinpoint accuracy.

We're seeking an architect, not a traditional manager. You'll dive deep into platforms like NetSuite and Ramp, identifying opportunities to enhance or completely reimagine them with more intelligent, streamlined AI solutions. From tuition collection to ESA reimbursements, tax documentation to audit preparation—you'll ensure every financial process runs flawlessly and invisibly. We're not interested in someone who merely "streamlines processes." We want someone who eliminates them entirely. If you believe conventional finance departments are inherently inefficient and see AI as the solution, here's your chance to prove it.

You'll not only witness our formula for building billion-dollar enterprises—you'll document it, perfect it, and replicate it repeatedly.

Are you prepared to engineer tomorrow's financial paradigm? Submit your application today.

What You Will Be Doing

• Architecting AI-powered financial systems that eliminate human touchpoints across revenue collection, reporting, compliance, and internal controls
• Developing sophisticated automations and implementing LLM technologies to replace error-susceptible manual tasks in NetSuite, Ramp, and complementary financial platforms
• Orchestrating frictionless execution of critical financial operations including tuition processing, ESA payments, tax documentation, and audit preparation at enterprise scale
• Developing audit-ready financial statements and reporting mechanisms capable of seamless expansion across multiple educational business verticals
• Persistently refining and reconstructing financial infrastructure to support billion-dollar business units without expanding headcount
  
  

What You Won’t Be Doing

• Overseeing a substantial finance department—your focus will be on systems architecture, not personnel management
• Monitoring routine month-end closings or manually reviewing transaction approvals
• Settling for "industry standard" ERP workflows—your mandate is to identify inefficiencies and eliminate them
• Assigning tedious tasks to subordinates—your leadership style is hands-on and example-setting
• Maintaining status quo operations—we operate in an environment of explosive growth, not steady-state management
  
  

Group Finance Director Key Responsibilities

Create an autonomous, AI-integrated financial ecosystem capable of supporting multiple billion-dollar educational ventures with zero manual intervention, ensuring complete scalability and operational excellence across all financial functions.

Basic Requirements

• Professional financial certification (CPA, ACA, ACCA, CIMA, CFA, or MBA)
• Demonstrated financial or accounting leadership in an organization with $100M+ revenue
• Either 5+ years as an auditor with a top 10 global accounting firm, or direct experience managing at least 5 audits by such firms
• Proven expertise with enterprise-grade ERP platforms (such as NetSuite, SAP)
• Demonstrated application of generative AI tools (ChatGPT, Claude, Gemini, etc.) in professional financial contexts
• Geographic location within UTC-8 to UTC+3 time zones
  
  

Nice-to-have Requirements

• Knowledge of U.S. K-12 education models and structures (private schools, charter institutions, ESA programs)
• Track record of developing finance automation solutions or AI-enhanced workflows from conception to implementation
• Prior experience with financial operations in complex multi-entity, multi-jurisdiction corporate structures
  
  

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.015