Corporate Financial Controller, Trilogy (Remote) - $400,000/year USD

Ready to revolutionize finance in education? This isn't about maintaining spreadsheets—it's about architecting the future.

At Trilogy, we're reimagining education across multiple breakthrough businesses. Behind every innovative K-12 school and cutting-edge EdTech platform stands a finance infrastructure that must be as visionary as our educational models. We need someone who can build that backbone.

As our Corporate Financial Controller, you'll create lean, AI-powered systems that render traditional finance departments obsolete. You'll own the financial architecture supporting millions of students while eliminating complexity at every turn. No bloated teams, no bureaucratic processes—just elegant systems that scale.

You'll collaborate directly with executive leadership, turning financial insights into educational impact. Your infrastructure decisions will directly influence how we expand, innovate, and transform learning experiences worldwide.

If you're ready to engineer financial systems that power education's future, we're waiting for you.

What You Will Be Doing

• Crafting next-generation finance infrastructure with AI at its core, supporting rapid educational business growth
• Authoring strategic Design Decisions that eliminate complexity and create scalable financial workflows
• Providing expert written feedback on Deep Dives and Improvement Plans to elevate both human and AI performance
• Engaging in strategic discussions around budgeting, business expansion, vendor relationships, and regulatory compliance
• Orchestrating seamless financial operations across tuition management, audit processes, and tax compliance at scale
  
  

What You Won’t Be Doing

• Overseeing a conventional finance department with numerous direct reports
• Micromanaging month-end close procedures or transaction approvals
• Settling for out-of-the-box ERP solutions without customization
• Pushing essential tasks downward—you'll be hands-on in system building
• Operating in a predictable, slow-moving environment—our pace is rapid and transformative
  
  

Corporate Financial Controller Key Responsibilities

Design, implement and maintain a streamlined, AI-enhanced financial ecosystem that drives multiple education ventures toward exponential growth—eliminating inefficiency while maximizing scalability.

Basic Requirements

• Professional finance certification (CPA, ACA, ACCA, CIMA, CFA, or MBA)
• Minimum 10 years in progressive finance leadership positions (Finance Manager, Controller, CFO or equivalent), demonstrating increasing scope and responsibility
• Proven track record in executive finance roles (SVP, CFO or similar) with comprehensive oversight of core finance functions
• Expert-level knowledge of US GAAP and integrated financial reporting
• Extensive experience implementing and optimizing ERP platforms (NetSuite, SAP, etc.) in multi-entity organizational structures
• Successfully managed or participated in 5+ Big 4 external audits, from either client or auditor perspective
• Superior written and verbal communication skills in English, capable of effective executive-level engagement
• Located within UTC-8 to UTC+3 time zones
  
  

Nice-to-have Requirements

• Knowledge of US K-12 education models, including private schools, charter systems, and ESA program structures
• Track record of building finance automation systems or implementing AI-driven financial workflows
• Prior experience navigating finance operations across multiple legal 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-CorporateFinan.020