Most finance executives inherit a system. 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. 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.



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. Running finance as a reporting factory.

Closing the books and producing audit workpapers are the Controller's responsibilities. Building a large finance organization to handle complexity. 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.

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; 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. 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. Strong written and verbal English, with experience communicating directly with CEOs, boards, lenders, or capital partners.

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. Hundreds of software businesses run on the Trilogy Business Platform. Our technological innovation is spearheaded by a passion for simple customer-facing designs.

Our incubation of recent businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. 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.

📌 Deputy Chief Financial Officer, Trilogy (Remote) (Montreal)
🏢 Crossover
📍 Montreal