Division CFO, Trilogy (Remote) - $400,000/year USD

You didn’t earn your chops in PE, IB, or Big 4 M&A just to babysit budgets and bless PowerPoint decks.

What You Will Be Doing

• Building and operating 3-statement models with explicit drivers, integrated ERP outputs, and AI-enhanced scenario testing.
• Producing full investment packs — models, sensitivity analysis, and board-ready memos — in under 72 hours.
• Pressure-testing CAC, retention, pricing, utilization, and other levers to drive clarity and surface high-impact assumptions.
• Redesigning fragile business plans into sequenced, measurable execution paths with KPI guardrails.
• Owning and refining live financial systems that power real-time decisions across SaaS and education portfolios.
  
  

What You Won’t Be Doing

• Closing the books, filing audits, or spending your time on compliance — this is not a controller or FP&A manager role.
• Managing large teams or playing career counselor — you lead through output, not headcount.
• Creating decks that die in inboxes — every recommendation must be backed by models, tested assumptions, and a clear go/no-go path.
• Operating in cruise control — this is a high-tempo, AI-native, ambiguity-rich environment by design.
• Asking for permission to think big — your remit is to interrogate strategy and make it sharper, faster.
  
  

Division CFO Key Responsibilities

Architect and operate an AI-integrated financial system that drives high-stakes investment decisions, scalable growth, and executional clarity across fast-scaling SaaS and education ventures.

Basic Requirements

• 5+ years in PE, IB, or Big 4 M&A/Corporate Finance (not audit/tax), with direct exposure to deal modeling, client/board interaction, and investment decisions.
• CPA, ACA, ACCA, CFA, CIMA, or MBA, with deep knowledge of US GAAP/IFRS and integrated financial statements.
• Prior experience with enterprise-grade ERP systems (e.g., NetSuite, Oracle, SAP).
• Demonstrated use of AI as a co-pilot for modeling, scenario planning, research, memo drafting, and automation.
• Track record of producing models and board-level recommendations with speed, polish, and strategic clarity.
• Located within UTC-8 to UTC+3 time zones.
  
  

Nice-to-have Requirements

• Exposure to SaaS or EdTech business models.
• Experience architecting financial systems, not just modeling within them.
• Prior experience in ambiguous, founder-led environments with evolving scope and high-candor cultures.
  
  

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-GroupChiefFina.015