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

Your background in PE, IB, or Big 4 M&A wasn't earned to oversee budget cycles or rubber-stamp presentation slides.

You're positioned to design, challenge, and drive forward — converting complex strategy into execution frameworks that hold up under scrutiny, not multi-year projections that sit untouched. Financial modeling under high-stakes conditions is second nature to you. You're ready to apply that expertise where it directly influences operational roadmaps, beyond investment documentation alone. This role delivers that opportunity.

Trilogy seeks a finance strategist with operational instincts and deal-level precision: a professional who excels in uncertainty, takes ownership of results, and integrates AI as a core working tool. You'll collaborate directly with founders and leadership to define the direction of SaaS or education businesses, constructing the financial infrastructure and investment logic that enable intelligent scaling without excess.

If your preferred workweek involves dissecting a flawed business case, reconstructing it with phased objectives and KPI boundaries, and delivering analysis that commands executive attention, this is the environment for you.

You will not oversee 30-person departments. You will not audit budgets. You will not wait years to see results. You will drive strategy with velocity, discipline, and AI-supported accuracy, and your contributions will directly influence ventures that are reshaping industries.

What You Will Be Doing

• Constructing and maintaining integrated 3-statement models with transparent drivers, ERP system outputs, and AI-supported scenario analysis.
• Delivering complete investment packages — financial models, sensitivity frameworks, and executive-ready memoranda — within 72 hours.
• Stress-testing CAC, retention, pricing, utilization, and other operational levers to uncover clarity and identify material assumptions.
• Transforming unstable business plans into phased, trackable execution roadmaps with KPI control mechanisms.
• Managing and evolving live financial infrastructure that enables real-time decision-making across SaaS and education portfolios.
  
  

What You Won’t Be Doing

• Managing month-end close, audit filings, or compliance workflows — this is not a controller or FP&A management position.
• Leading large teams or handling personnel development — influence is delivered through work quality, not team size.
• Producing slide decks that never get acted upon — every proposal must be supported by models, validated assumptions, and a definitive decision path.
• Working at a steady, predictable pace — this is intentionally a high-speed, AI-native, ambiguity-heavy setting.
• Waiting for approval to challenge assumptions — your role is to interrogate strategy and refine it with urgency.
  
  

Director Of Finance Strategy Key Responsibilities

Design and maintain an AI-enabled financial infrastructure that supports critical investment decisions, scalable expansion, and operational precision across rapidly growing SaaS and education ventures.

Basic Requirements

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

Nice-to-have Requirements

• Familiarity with SaaS or EdTech operating models.
• Experience designing financial systems from the ground up, not only working within existing frameworks.
• Background in dynamic, founder-driven settings with shifting 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-SG-COUNTRY-DirectorofFina.007

Trilogy is known for relentlessly seeking top talent, innovating new technology, and incubating new businesses. Their technological innovation is spearheaded by a passion for simple customer-facing designs, and their incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack.