You didn't refine your expertise in private equity, investment banking, or Big 4 M&A advisory to spend your days policing spreadsheets and rubber-stamping presentation decks.Your role is to design, challenge, and drive forward—transforming ambiguous strategy into resilient execution frameworks, not multi-year projections that gather dust. You've honed the discipline of financial modeling in high-pressure environments. Now you're ready to deploy that expertise where it directly influences live operating strategies, not just deal books. This is that opportunity.Trilogy seeks a finance strategist with operational instincts and transactional precision: someone who excels in uncertainty, takes ownership of results, and uses AI as an integrated thinking tool. You'll collaborate closely with founders and senior leaders to define the trajectory of SaaS and education ventures, constructing the financial infrastructure and decision frameworks that enable intelligent scaling without excess.If your ideal workweek involves dissecting a flawed strategic plan, reconstructing it with phased milestones and rigorous KPI controls, and delivering a memo that commands executive attention, this role is designed for you.You will not be overseeing large teams. You will not be enforcing budgets. You will not be waiting years to see results. You'll be influencing strategy with velocity, discipline, and AI-augmented precision—and your contributions will alter the course of ventures reshaping entire markets.
What You Will Be Doing
- Constructing and maintaining integrated 3-statement financial models with transparent drivers, ERP system integration, and AI-powered scenario analysis.
- Delivering complete investment packages—including models, sensitivity frameworks, and executive-ready memos—within 72 hours.
- Stress-testing customer acquisition cost, retention metrics, pricing structures, utilization rates, and other critical levers to expose key assumptions and drive strategic clarity.
- Transforming unstable business plans into structured, milestone-driven execution roadmaps with embedded KPI safeguards.
- Managing and continuously improving live financial systems that support real-time decision-making across SaaS and education portfolios.
What You Won’t Be Doing
- Handling month-end close, audit preparation, or compliance workflows—this is not a controller or FP&A management position.
- Building or supervising large teams—your influence stems from the quality of your work, not the size of your org chart.
- Producing slide decks that languish unopened—every strategic recommendation must rest on tested models, validated assumptions, and actionable decision paths.
- Working at a comfortable, predictable pace—this is a high-intensity, AI-first environment deliberately designed for complexity and speed.
- Waiting for approval before challenging direction—you are expected to interrogate strategy and sharpen it proactively.
Portfolio Finance Director Key Responsibilities
Design and operate an AI-enabled financial infrastructure that informs high-impact investment choices, sustainable growth, and operational precision across rapidly scaling SaaS and education businesses.
Basic Requirements
- 5+ years of experience in private equity, investment banking, or Big 4 M&A/Corporate Finance (excluding audit/tax), with hands-on involvement in deal modeling, client/board engagement, and investment analysis.
- Professional certification (CPA, ACA, ACCA, CFA, CIMA) or MBA, combined 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 tools to support modeling, scenario development, analytical research, memo creation, and workflow automation.
- Demonstrated ability to deliver polished financial models and board-level strategic recommendations with speed and clarity.
- Based within UTC-8 to UTC+3 time zones.
Nice-to-have Requirements
- Familiarity with SaaS or EdTech operating models.
- Background in designing financial systems and infrastructure, beyond modeling alone.
- Experience working in founder-driven, fast-evolving organizations with direct feedback cultures and fluid responsibilities.
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.005
