Director of Finance Strategy, Trilogy

Director of Finance Strategy, Trilogy (Remote) - $400,000/year USDThe 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/hrOverviewYour experience in PE, IB, or Big 4 M&A was not meant for budget maintenance and deck approvals. You’re here to design, challenge, and drive momentum — transforming ambiguous strategy into robust execution frameworks, not multi‑year projections that collect dust. You've proven your ability to build financial models in high‑pressure environments. Now you’re ready to deploy that expertise where it directly influences operating decisions, not just pitch books. This role delivers that opportunity.Trilogy seeks a finance strategist with operational instincts and deal‑maker precision: someone who excels in uncertainty, takes ownership of results, and uses AI as a force multiplier. You’ll partner directly with founders and senior leaders to define the future of SaaS or education businesses, creating the financial infrastructure and investment logic that enable intelligent scaling, not unchecked 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 be overseeing large finance teams, enforcing budget compliance, or waiting years to see impact. You’ll be influencing strategy with velocity, discipline, and AI‑augmented rigor, and your contributions will redirect ventures that are reshaping industries.What You Will Be DoingConstructing and maintaining 3‑statement models with transparent drivers, integrated ERP data, and AI‑powered scenario analysis.Delivering complete investment packages — financial models, sensitivity frameworks, and board‑ready documentation — within 72 hours.Stress‑testing CAC, retention, pricing, utilization, and similar metrics to generate insight and expose critical assumptions.Transforming weak business plans into structured, trackable execution roadmaps supported by KPI thresholds.Managing and evolving live financial platforms that enable real‑time decision‑making across SaaS and education portfolios.What You Won’t Be DoingManaging month‑end close, audit filings, or compliance workflows — this is not a controller or FP&A management position.Building or supervising large teams — your influence comes from deliverables, not org charts.Producing presentations that go unread — every proposal must be supported by rigorous models, validated assumptions, and a clear decision framework.Working at a predictable pace — this is a fast‑moving, AI‑native, high‑ambiguity environment by intention.Waiting for approval to challenge convention — your mandate is to scrutinize strategy and sharpen its execution.Director Of Finance Strategy Key ResponsibilitiesDesign and manage an AI‑enhanced financial infrastructure that supports high‑impact investment decisions, scalable expansion, and operational precision across rapidly growing SaaS and education ventures.Basic Requirements5+ years in PE, IB, or Big 4 M&A/Corporate Finance (not audit/tax), with direct involvement in deal modeling, client/board engagement, and investment decisions.CPA, ACA, ACCA, CFA, CIMA, or MBA, with strong command of US GAAP/IFRS and integrated financial statements.Prior experience with enterprise‑grade ERP systems (e.g., NetSuite, Oracle, SAP).Demonstrated use of AI as a co‑pilot for modeling, scenario planning, research, memo drafting, and automation.Track record of producing models and board‑level recommendations with speed, polish, and strategic clarity.Located within UTC‑8 to UTC+3 time zones.Nice‑to‑have RequirementsExposure to SaaS or EdTech business models.Experience architecting financial systems, not just modeling within them.Prior experience in ambiguous, founder‑led environments with evolving scope and high‑candor cultures.About TrilogyHundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for three 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 usThis is a full‑time (40 hours per week) 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