Director of Finance Strategy, Trilogy

Director of Finance Strategy, Trilogy (Remote) – $400,000/year USD Join to apply for the Director of Finance Strategy, Trilogy (Remote) – $400,000/year USD role at Crossover. Base pay range $200.00/hr – $200.00/hr You didn't build your expertise in private equity, investment banking, or Big 4 M&A to spend your days managing budgets and approving slide decks. Your role is to design, challenge, and drive forward—converting ambiguous strategy into robust execution frameworks, not decade-long projections that gather dust. You've honed financial modeling under intense conditions. Now you seek to apply that expertise where it influences real operating models, not merely investment pitches. This is that opportunity. Trilogy seeks a finance strategist with operational instincts and deal-making precision: someone who excels in uncertainty, takes ownership of results, and employs AI as a force multiplier. You'll collaborate directly with founders and senior leaders to define the trajectory of SaaS or education businesses, designing the financial infrastructure and capital allocation frameworks that enable intelligent scaling, not inefficient growth. If your ideal workweek involves dismantling a weak business case, reconstructing it with phased milestones and KPI safeguards, and delivering a brief that commands the executive team's full attention, this role fits. You won't be overseeing 30-person departments. You won't be enforcing budget compliance. You won't be waiting years to see results. You'll be driving strategy with velocity, discipline, and AI-powered accuracy, and your contributions will alter the course of ventures reshaping industries. What You Will Be Doing Constructing and maintaining 3-statement financial models with transparent drivers, integrated ERP data flows and AI-supported scenario analysis. Delivering complete investment packages—financial models, sensitivity frameworks, and board-ready documentation—within 72 hours. Stress-testing customer acquisition cost, retention rates, pricing structures, utilization metrics, and other critical levers to expose high-impact assumptions and drive strategic clarity. Transforming unstable business plans into structured, trackable execution roadmaps anchored by KPI controls. Managing and continuously improving live financial infrastructure that supports real-time decision-making across SaaS and education portfolios. What You Won’t Be Doing Managing month-end close, audit processes, or compliance activities—this is not a controller or FP&A management position. Building or supervising large teams or serving as a people manager—you drive impact through deliverables, not direct reports. Producing presentations that go unread—every strategic recommendation must be underpinned by rigorous models, validated assumptions, and actionable decision paths. Working at a steady, predictable pace—this is an intentionally fast-moving, AI-first, high-ambiguity setting. Waiting for approval to challenge convention—your mandate is to scrutinize strategy and refine it with speed and precision. Director Of Finance Strategy Key Responsibilities Design and manage an AI-enhanced financial infrastructure that informs critical investment choices, supports scalable expansion, and ensures executional precision across rapidly growing SaaS and education businesses. Basic Requirements 5+ years in private equity, investment banking, or Big 4 M&A/Corporate Finance (excluding audit/tax), with hands-on experience in deal modeling, board/client engagement, and investment analysis. CPA, ACA, ACCA, CFA, CIMA, or MBA, with comprehensive understanding of US GAAP/IFRS and integrated financial statement preparation. Prior hands-on experience with enterprise ERP platforms (e.g., NetSuite, Oracle, SAP). Proven ability to leverage AI as a productivity tool for financial modeling, scenario generation, research, memo creation, and process automation. Demonstrated history of delivering financial models and executive-level strategic recommendations with speed, quality, 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 using existing frameworks. Experience operating in ambiguous, founder-driven settings characterized by dynamic scope and direct, candid communication. 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