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

You didn't sharpen your skills in Big 4 M&A, IB, or PE to spend your days managing budgets and rubber-stamping slide decks.

You're here to design, challenge, and drive—transforming ambiguous strategy into disciplined execution frameworks, not multi-year projections that collect dust. You've honed the discipline of financial modeling in high-pressure environments. Now you're ready to apply that expertise where it influences real operating decisions, not just pitch books. This is that opportunity.

Trilogy seeks a finance strategist with operational instincts and deal-sharpened judgment: someone who excels in uncertainty, takes ownership of results, and uses AI as an extension of their thinking. You'll partner directly with founders and senior leaders to define the trajectory of SaaS and education businesses, creating the financial infrastructure and decision frameworks that enable intelligent scaling—not headcount bloat.

If your ideal workweek involves dismantling a flawed business case, reconstructing it with sequenced milestones and metric-driven safeguards, and delivering a memo that commands executive attention, you belong here.

You won't oversee 30-person departments. You won't enforce budget compliance. You won't wait years to see results. You'll be driving strategy with velocity, precision, and AI-augmented rigor—and your contributions will reshape ventures that are redefining their industries.

What You Will Be Doing

• Constructing and maintaining integrated 3-statement models with explicit assumptions, ERP-linked data, and AI-powered scenario analysis.
• Delivering complete investment packages—financial models, sensitivity frameworks, and executive-ready memos—within 72 hours.
• Stress-testing key business drivers like CAC, retention, pricing, and utilization to expose critical assumptions and clarify strategic direction.
• Transforming weak business plans into structured, milestone-driven execution roadmaps with KPI-based accountability.
• Managing and evolving real-time financial systems that support decision-making across a portfolio of SaaS and education companies.
  
  

What You Won’t Be Doing

• Managing month-end close, preparing audits, or dedicating time to compliance functions—this is not a controller or FP&A management position.
• Building or supervising large teams—your influence comes from the quality of your work, not the size of your org chart.
• Producing presentations that languish unused—every proposal must be grounded in robust models, validated logic, and clear decision criteria.
• Working at a leisurely pace—this role demands intensity, AI fluency, and comfort with ambiguity by design.
• Waiting for approval to challenge assumptions—you're expected to interrogate strategy and sharpen it relentlessly.
  
  

Division CFO Key Responsibilities

Design and maintain an AI-powered financial infrastructure that informs critical investment choices, supports scalable expansion, and brings operational precision to rapidly growing SaaS and education ventures.

Basic Requirements

• 5+ years in IB, PE, or Big 4 M&A/Corporate Finance (excluding audit/tax), including hands-on deal modeling, board or client engagement, and investment decision support.
• CPA, ACA, ACCA, CFA, CIMA, or MBA, with comprehensive understanding of US GAAP/IFRS and consolidated financial statements.
• Hands-on experience with enterprise ERP platforms (e.g., NetSuite, Oracle, SAP).
• Proven application of AI tools for modeling, scenario design, research, memo creation, and process automation.
• History of delivering models and executive-level recommendations with speed, professionalism, and strategic insight.
• Based in UTC-8 to UTC+3 time zones.
  
  

Nice-to-have Requirements

• Familiarity with SaaS or EdTech operating models.
• Background in designing financial systems, not only working within existing ones.
• Experience in fast-moving, founder-driven settings with fluid priorities and direct feedback 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-MY-KualaLum-GroupChiefFina.017