Deputy Chief Financial Officer, Trilogy (Remote) - $800,000/year USD

Most finance executives inherit a system. You will redesign one, then decide where the capital goes. Trilogy is looking for the executive who can turn a portfolio of businesses into a capital allocation system: continuously ranking where the next dollar should go, backing those decisions with rigorous models, and moving capital toward its highest-return uses. You will own the calls that matter: fund or kill a business line; invest or hold; acquire or walk away; refinance or pay down debt. Every recommendation must connect strategy to cash, liquidity, covenants, risk, and enterprise value. Just as important, you will architect an AI-native finance function built to scale without decision bottlenecks. This does not mean sprinkling AI tools onto a traditional finance organization. You will redesign reporting, planning, controls, portfolio monitoring, and decision support around what AI and automation can now do. You won't need to personally build every workflow, but you must use AI deeply enough to know its edges: where it accelerates analysis, where it fails, and where expert judgment must take over. The result should be a smaller, more senior, higher-leverage finance organization rather than a growing pyramid of people and processes. You will operate directly with Trilogy's CEO, board, lenders, and capital partners, with personal accountability for the financial truth behind major decisions. As Deputy CFO, you will be the direct deputy carrying this mandate day to day. This is an $800K W-2 salaried role for someone who has already earned credibility at serious financial scale and now wants the mandate to compound enterprise value across an entire portfolio. If you want your impact measured by the quality of your capital decisions and the financial system you leave behind, apply. What You Will Be Doing • Allocating capital across the portfolio: Run capital and portfolio reviews, rank competing uses of capital on risk-adjusted return, and make clear fund, hold, restructure, exit, debt-paydown, or acquisition recommendations. • Architecting an AI-native finance system: Redesign planning, reporting, consolidation, controls, portfolio monitoring, and financial workflows around AI, automation, and scalable systems rather than additional headcount. • Driving investments and transactions: Build and defend the financial case for strategic investments, M&A, financing, and refinancing, including integrated models, downside scenarios, capital structure, covenant implications, and execution plans. • Owning board and capital-partner communication: Give the CEO, board, lenders, and capital partners fast, quantified, defensible truth, with recommendations that make the decision and trade-offs explicit. • Building a high-leverage finance leadership team: Set the bar for a small group of exceptional finance leaders while creating systems that allow new ventures and greater complexity to be absorbed without linear organizational growth. What You Won’t Be Doing • Running finance as a reporting factory. Closing the books and producing audit workpapers are the Controller's responsibilities. Your job is to turn financial information into better capital decisions. • Building a large finance organization to handle complexity. Scale should come from better systems, AI leverage, automation, and exceptional people, not layers of management. • Adding AI as a superficial productivity tool. You will architect workflows around its real capabilities and limitations, which requires substantial firsthand use. • Producing strategy decks without financial consequences. Major recommendations must carry the integrated model, downside case, capital implications, and execution guardrails behind them. • Managing the board through narrative. The numbers, assumptions, risks, and recommended action should be clear enough to withstand scrutiny. Deputy Chief Financial Officer Key Responsibilities Build a durable, AI-native finance function that compounds enterprise value across Trilogy's portfolio by allocating capital to its highest-return uses and creating financial systems and controls that scale without decision bottlenecks. Basic Requirements • Experience as the most senior finance decision-maker, or their direct deputy, for a business or portfolio with $100M+ in annual revenue across multiple legal entities. • Personal ownership of major capital-allocation decisions, including the ability to explain what was funded, reduced, or rejected; the dollars involved; the trade-offs; and your recommendation. • Decision ownership on at least one $25M+ closed M&A, financing, or refinancing transaction, with direct responsibility for negotiation, financing selection, board recommendation, or post-close integration. • Direct experience presenting to and taking live questions from a board of directors. • Ownership of an external audit relationship under US GAAP or IFRS, directly or through a Controller reporting to you. • Hands-on experience with a true enterprise ERP such as SAP, NetSuite, Oracle, Workday, or equivalent. • Recent experience re-architecting a finance workflow around AI, with enough regular personal AI use to understand where the technology is reliable, where it is not, and how those boundaries should shape finance-system design. • Ability to operate integrated 3-statement models and defend assumptions, downside scenarios, covenant math, capital structure, and recommendations under live questioning. • Strong written and verbal English, with experience communicating directly with CEOs, boards, lenders, or capital partners. • Located within the UTC−8 to UTC+3 time-zone range. Nice-to-have Requirements • CPA, ACA, ACCA, CIMA, CFA, MBA, or comparable finance credential. • Earlier career experience in private equity, investment banking, M&A, corporate finance, or another environment requiring rigorous modeling and high-stakes capital decisions. • Experience rebuilding a finance function rather than simply inheriting and operating one. • Experience across a portfolio, multi-entity, or PE-backed operating environment. 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 in 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 $400 USD/hour, which equates to $800,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faq

Experience as the most senior finance decision-maker, or their direct deputy, for a business or portfolio with $100M+ in annual revenue across multiple legal entities. Personal ownership of major capital-allocation decisions, including the ability to explain what was funded, reduced, or rejected; the dollars involved; the trade-offs; and your recommendation. Decision ownership on at least one $25M+ closed M&A, financing, or refinancing transaction, with direct responsibility for negotiation, financing selection, board recommendation, or post-close integration. Direct experience presenting to and taking live questions from a board of directors. Ownership of an external audit relationship under US GAAP or IFRS, directly or through a Controller reporting to you. Hands-on experience with a true enterprise ERP such as SAP, NetSuite, Oracle, Workday, or equivalent. Recent experience re-architecting a finance workflow around AI, with enough regular personal AI use to understand where the technology is reliable, where it is not, and how those boundaries should shape finance-system design. Ability to operate integrated 3-statement models and defend assumptions, downside scenarios, covenant math, capital structure, and recommendations under live questioning. Strong written and verbal English, with experience communicating directly with CEOs, boards, lenders, or capital partners. Located within the UTC−8 to UTC+3 time-zone range.

Allocating capital across the portfolio: Run capital and portfolio reviews, rank competing uses of capital on risk-adjusted return, and make clear fund, hold, restructure, exit, debt-paydown, or acquisition recommendations. Architecting an AI-native finance system: Redesign planning, reporting, consolidation, controls, portfolio monitoring, and financial workflows around AI, automation, and scalable systems rather than additional headcount. Driving investments and transactions: Build and defend the financial case for strategic investments, M&A, financing, and refinancing, including integrated models, downside scenarios, capital structure, covenant implications, and execution plans. Owning board and capital-partner communication: Give the CEO, board, lenders, and capital partners fast, quantified, defensible truth, with recommendations that make the decision and trade-offs explicit. Building a high-leverage finance leadership team: Set the bar for a small group of exceptional finance leaders while creating systems that allow new ventures and greater complexity to be absorbed without linear organizational growth.