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SVP of Finance

$400,000 USD/year
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Director of Academics

$400,000 USD/year
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SVP of Technical Product Management

$400,000 USD/year
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AI-First Chief Product Officer

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AI-First VP of Sales

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AI-First Lead Product Owner

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Principal AI Engineer

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AI Super Engineer

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AI-First Senior QA Engineer

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AI-First Full-Stack Software Engineer

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Senior DevOps Engineer

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AI-Driven Social Studies Learning Strategist

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AI-Driven Math Learning Strategist

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AI-Augmented Product Engineer

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Software Engineer II

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Customer Support Representative

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Senior Admissions Specialist

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SVP of Finance @ Trilogy

$400,000 USD/year
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Fully-remote
Remote
full-time (40 hrs/week)
Flexible schedule
Long-term role

Key responsibilities

Architect and operate an AI-integrated financial system that drives high-stakes investment decisions, scalable growth, and executional clarity across fast-scaling SaaS and education ventures.

Description

You didn’t earn your chops in PE, IB, or Big 4 M&A just to babysit budgets and bless PowerPoint decks.

You’re here to architect, interrogate, and accelerate — turning messy strategy into bulletproof execution plans, not five-year forecasts that get ignored. You’ve mastered the art of financial modeling under pressure. Now you want to wield that skill where it shapes actual operating plans, not just investment memos. This is that role.

Trilogy is looking for a finance strategist with an operator’s instinct and a dealmaker’s clarity: someone who thrives in ambiguity, owns outcomes, and leverages AI like a second brain. You’ll work directly with founders and executives to shape the future of SaaS or education ventures, building the financial systems and investment frameworks that let these companies scale smart, not bloated.

If your ideal week includes tearing apart a shaky business plan, rebuilding it with sequenced milestones and KPI guardrails, and dropping a memo that makes the exec team shift in their seats, you’re in the right place.

You won’t be managing 30-person teams. You won’t be policing budgets. You won’t be waiting a decade for impact. You’ll be shaping strategy with speed, rigor, and AI-enabled precision, and your work will change the trajectory of ventures that are changing the world.

Candidate requirements

  • 5+ years in PE, IB, or Big 4 M&A/Corporate Finance (not audit/tax), with direct exposure to deal modeling, client/board interaction, and investment decisions.
  • CPA, ACA, ACCA, CFA, CIMA, or MBA, with deep knowledge of US GAAP/IFRS and integrated financial statements.
  • Prior experience with enterprise-grade ERP systems (e.g., NetSuite, Oracle, SAP).
  • Demonstrated use of AI as a co-pilot for modeling, scenario planning, research, memo drafting, and automation.
  • Track record of producing models and board-level recommendations with speed, polish, and strategic clarity.
  • Located within UTC-8 to UTC+3 time zones.

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.

Accept Job Offer.
STEP 5

Accept Job Offer.

Pass 
proctored test.
ONE LAST THING

Pass 
proctored test.

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.

Companies that trust Crossover

Hiring now

To find the best person in the world, not the best person in their zipcode.

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