Portfolio Finance Director, Trilogy (Remote) - 400,000/year USD

You didn\’t build your expertise in PE, IB, or Big 4 M&A just to review budgets and approve slide decks.

You\’re here to design, challenge, and drive forward — transforming ambiguous strategy into airtight execution roadmaps, not multi-year projections that collect dust. You\’ve honed the discipline of financial modeling in high-pressure settings. Now you\’re ready to apply that capability where it informs real operational plans, not merely investment decks. This role delivers that opportunity.

Trilogy seeks a finance strategist with operational instincts and dealmaker precision: someone who excels amid uncertainty, takes ownership of results, and uses AI as a force multiplier. You\’ll collaborate directly with founders and senior leaders to define the trajectory of SaaS or education businesses, establishing the financial infrastructure and investment logic that enable intelligent scaling, not wasteful growth.

If your ideal workweek involves dissecting a flawed business case, reconstructing it with phased milestones and KPI boundaries, and delivering a memo that commands executive attention, this is your opportunity.

You won\’t oversee 30-person departments. You won\’t police expense lines. You won\’t wait years to see results. You\’ll drive strategy with velocity, discipline, and AI-amplified rigor, and your contributions will alter the course of ventures with global impact.

What You Will Be Doing

• Constructing and maintaining 3-statement models with granular drivers, integrated ERP data, and AI-powered scenario analysis.
• Delivering complete investment packages — models, sensitivity frameworks, and board-ready documentation — within 72 hours.
• Stress-testing CAC, retention, pricing, utilization, and other critical levers to generate insight and expose key assumptions.
• Transforming fragile business plans into phased, trackable execution frameworks with defined KPI thresholds.
• Managing and refining dynamic financial systems that enable real-time decision-making across SaaS and education portfolios.

What You Won\’t Be Doing

• Closing monthly books, managing audits, or dedicating time to compliance work — this is not a controller or FP&A manager position.
• Building or managing large teams or serving as a mentor figure — you influence through deliverables, not org chart size.
• Producing presentations that go unread — every proposal must be grounded in models, validated assumptions, and actionable decision paths.
• Working at a steady, predictable pace — this is a fast-moving, AI-native, ambiguity-heavy environment by intent.
• Waiting for approval to challenge the status quo — your role is to scrutinize strategy and strengthen it with urgency.

Portfolio Finance Director Key Responsibilities
Design and operate an AI-enhanced financial infrastructure that supports critical investment decisions, sustainable growth, and operational precision across rapidly expanding 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 evaluation.
• CPA, ACA, ACCA, CFA, CIMA, or MBA, with comprehensive understanding of US GAAP/IFRS and consolidated financial statements.
• Prior hands-on experience with enterprise-grade ERP platforms (e.g., NetSuite, Oracle, SAP).
• Proven application of AI as a productivity partner for modeling, scenario development, research, memo creation, and process automation.
• Verifiable history of delivering models and board-level insights with efficiency, precision, and strategic impact.
• Based within 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 ambiguous, founder-driven organizations 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