Director of Finance Strategy, Trilogy

Director of Finance Strategy, Trilogy (Remote) - $400,000/year USD 1 day ago Be among the first 25 applicants This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range $200.00/hr - $200.00/hr Your experience in private equity, investment banking, or Big 4 M&A wasn’t meant for budget maintenance and PowerPoint approval cycles. Your role is to design, challenge, and drive forward — transforming unclear strategy into rigorous execution frameworks, not multi-year projections that never get revisited. Financial modeling under time constraints is a skill you’ve honed. Now you’re ready to apply it where it influences real operational roadmaps, not solely deal documentation. This opportunity delivers exactly that. Trilogy seeks a finance strategist with operational instincts and transaction-level precision: someone comfortable with uncertainty, accountable for results, and fluent in using AI as an analytical partner. You’ll collaborate directly with founders and leadership to define the trajectory of SaaS and education businesses, designing the financial infrastructure and investment logic that enable intelligent scaling, not unchecked expansion. If your preferred workweek involves dissecting a flawed business case, reconstructing it with phased targets and performance thresholds, and delivering analysis that commands executive attention, this is your environment. You won’t oversee large finance departments. You won’t enforce budget compliance. You won’t wait years to see measurable impact. You’ll drive strategy with velocity, discipline, and AI-augmented tools, and your contributions will redirect the course of ventures reshaping industries. What You Will Be Doing Constructing and maintaining integrated 3-statement financial models with transparent assumptions, ERP data integration, and AI-powered scenario analysis. Delivering comprehensive investment packages — financial models, sensitivity cases, and executive-ready memoranda — within 72 hours. Stress-testing customer acquisition cost, retention rates, pricing structures, capacity utilization, and similar drivers to expose critical assumptions and clarify decision points. Transforming weak business plans into phased, trackable execution roadmaps anchored by performance indicators. Managing and iterating on dynamic financial systems that enable real-time decision-making across SaaS and education holdings. What You Won’t Be Doing Managing month-end close processes, audit filings, or compliance workflows — this is not a controllership or FP&A management position. Supervising large teams or performing people management functions — influence comes from the quality of your deliverables, not team size. Producing presentations that never drive action — every proposal must be grounded in tested models, validated assumptions, and explicit decision criteria. Working at a steady, predictable pace — this role is intentionally fast-moving, AI-enabled, and structured around ambiguity. Waiting for approval to challenge assumptions — you are expected to interrogate strategy and elevate its quality proactively. Director Of Finance Strategy Key Responsibilities Design and maintain an AI-enabled financial operating system that supports critical investment choices, sustainable expansion, and operational precision across high-growth SaaS and education companies. Basic Requirements 5+ years in private equity, investment banking, or Big 4 M&A/Corporate Finance (excluding audit/tax), including hands‑on deal modeling, stakeholder engagement, and participation in investment evaluation. CPA, ACA, ACCA, CFA, CIMA, or MBA qualification, with comprehensive understanding of US GAAP/IFRS and fully integrated financial statements. Practical experience working with enterprise ERP platforms (e.g., NetSuite, Oracle, SAP). Proven application of AI tools to support financial modeling, scenario development, research, memo preparation, and process automation. Documented ability to deliver polished financial models and executive-level recommendations rapidly and with strategic insight. Based in time zones ranging from UTC‑8 to UTC+3. Nice-to-have Requirements Familiarity with SaaS or EdTech operating models. Background in designing financial infrastructure, beyond simply building models within existing systems. Experience working in fluid, founder-driven settings characterized by shifting priorities and direct communication norms. 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. 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