Chief Financial Officer
$800,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Worldwide
Semi-flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role

Chief Financial Officer   $800,000 USD/year

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 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 will NOT 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.

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.

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.

Nice to have

  • 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.

Meet a successful candidate

Watch Interview
Nadia Dan
Nadia  |  Senior Software Engineer
Romania

Your first time will be flawed. Your 100th time will be flawed. But it takes dedication to get to the 1,000th time and become good. The cons...

Meet Nadia

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.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

School sucks. So we’re fixing it.

The education Olympics

The education Olympics

It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game. 

Salary without side gigs

Salary without side gigs

Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.

Skills make the grade

Skills make the grade

Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join America’s largest community of  AI first education leadersAI-first education leaders.