Deputy Chief Financial Officer, Trilogy; Remote

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, this is a $800K/year 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.

• 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.

• Running finance as a reporting factory. Closing the books and producing audit work papers 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.

Build a durable, AI-native finance function…