You didn’t hone your skills in Private Equity, Investment Banking, or Big 4 M&A just to manage spreadsheets and rubber-stamp presentations.You're here to design, question, and accelerate—transforming chaotic strategies into flawless execution plans, not just crafting five-year forecasts that gather dust. You've perfected financial modeling under pressure. Now, you're eager to apply that expertise to shape real operational plans, not just investment summaries. This is that opportunity.Trilogy seeks a finance strategist with an operator's mindset and a dealmaker's precision: someone who thrives amidst uncertainty, owns results, and uses AI as an extension of their intellect. You'll collaborate directly with founders and executives to define the future of SaaS or education ventures, constructing financial systems and investment frameworks that enable smart, scalable growth.If your ideal week involves dismantling a fragile business plan, reconstructing it with strategic milestones and KPI safeguards, and delivering a memo that makes the executive team take notice, you're in the right place.You won't be leading a 30-person team. You won't be overseeing budgets. You won't be waiting years for results. You'll be crafting strategy with speed, precision, and AI-enabled accuracy, and your work will alter the course of ventures that are reshaping the world.
What You Will Be Doing
- Crafting and managing 3-statement models with clear drivers, integrated ERP outputs, and AI-enhanced scenario analysis.
- Generating comprehensive investment packages — including models, sensitivity analyses, and board-ready memos — in less than 72 hours.
- Scrutinizing CAC, retention, pricing, utilization, and other levers to enhance clarity and reveal impactful assumptions.
- Transforming weak business plans into structured, measurable execution paths with KPI safeguards.
- Managing and improving live financial systems that enable real-time decision-making in SaaS and education portfolios.
What You Won’t Be Doing
- Handling book closures, audits, or compliance tasks — this role is not for a controller or FP&A manager.
- Managing large teams or serving as a career coach — you lead through deliverables, not team size.
- Creating presentations that go unnoticed — every suggestion must be supported by models, validated assumptions, and a definitive go/no-go approach.
- Operating on autopilot — this is an environment rich in ambiguity and driven by high tempo and AI.
- Seeking permission to innovate — your mission is to challenge strategy and refine it, quickly and effectively.
Portfolio Finance Director Key Responsibilities
Design and manage an AI-powered financial system that informs critical investment decisions, scalable growth, and executional clarity 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 interaction, and investment decision-making.
- CPA, ACA, ACCA, CFA, CIMA, or MBA, with comprehensive understanding of US GAAP/IFRS and integrated financial statements.
- Experience with enterprise-grade ERP systems (e.g., NetSuite, Oracle, SAP).
- Proven use of AI as an assistant for modeling, scenario planning, research, memo drafting, and automation.
- History of delivering models and board-level recommendations swiftly, with precision and strategic depth.
- Residing within UTC-8 to UTC+3 time zones.
Nice-to-have Requirements
- Familiarity with SaaS or EdTech business models.
- Experience in designing financial systems, beyond just modeling within them.
- Previous experience in ambiguous, founder-led environments with evolving roles and high-transparency 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-IN-COUNTRY-PortfolioFinan
