Director of Finance Strategy, Trilogy

Director of Finance Strategy, Trilogy (Remote) – $400,000/year USD Position is full‑time (40 hours per week), remote, and immediately available. Base pay range $200.00/hr – $200.00/hr You’ll architect, interrogate, and accelerate—turning messy strategy into bullet‑proof execution plans, not ignored forecasts. You’ve mastered financial modeling under pressure and now want to shape operating plans that drive real results. This is the role. Trilogy seeks a finance strategist with an operator’s instinct and a dealmaker’s clarity: someone who thrives in ambiguity, owns outcomes, and leverages AI as a second brain. You’ll work directly with founders and executives to build financial systems and investment frameworks that let these companies scale smart. What You Will Be Doing Build and operate 3‑statement models with explicit drivers, integrated ERP outputs, and AI‑enhanced scenario testing. Produce full investment packs—models, sensitivity analysis, and board‑ready memos—in under 72 hours. Pressure‑test CAC, retention, pricing, utilization, and other levers to drive clarity and surface high‑impact assumptions. Redesign fragile business plans into sequenced, measurable execution paths with KPI guardrails. Own and refine live financial systems that power real‑time decisions across SaaS and education portfolios. What You Won’t Be Doing Closing the books, filing audits, or spending time on compliance—this is not a controller or FP&A manager role. Managing large teams or playing career counselor—lead through output, not headcount. Creating decks that die in inboxes—every recommendation must be backed by models, tested assumptions, and a clear go/no‑go path. Operating in cruise control—this is a high‑tempo, AI‑native, ambiguity‑rich environment by design. Asking for permission to think big—the remit is to interrogate strategy and make it sharper, faster. Key Responsibilities Architect and operate an AI‑integrated financial system that drives high‑stakes investment decisions, scalable growth, and executional clarity across fast‑scaling SaaS and education ventures. Basic Requirements 5+ years in PE, IB, or Big 4 M&A/Corporate Finance (not audit/tax) with direct exposure to deal modeling, client/board interaction, and investment decisions. CPA, ACA, ACCA, CFA, CIMA, or MBA, with deep knowledge 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 Requirements Exposure 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 Trilogy Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our innovation is driven by a passion for simple, customer‑centric designs, and we grow together by tackling moon‑shot ideas to rearchitect existing projects for the modern cloud‑based stack. Working with Us This is a full‑time (40 hours per week) long‑term position, immediately available, and requires entering an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $200 USD per hour, equivalent to $400,000 USD per year, paid weekly. #J-18808-Ljbffr