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Chief Financial Officer @ Trilogy

$1,600,000 USD/year
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Worldwide
Semi-flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role

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.

Description

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. This is a $1.6M/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. If you want your impact measured by the quality of your capital decisions and the financial system you leave behind, apply.

Candidate 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.

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Why Crossover
Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.

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