Director of Finance Strategy, Trilogy (Remote) - $400,000 / year USD

Director of Finance Strategy, Trilogy (Remote) - $400,000 / year USD

This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$200.00 / hr - $200.00 / hr

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.

What You Will Be Doing

• Building and operating 3‑statement models with explicit drivers, integrated ERP outputs, and AI‑enhanced scenario testing.
• Producing full investment packs — models, sensitivity analysis, and board‑ready memos — in under 72 hours.
• Pressure‑testing CAC, retention, pricing, utilization, and other levers to drive clarity and surface high‑impact assumptions.
• Redesigning fragile business plans into sequenced, measurable execution paths with KPI guardrails.
• Owning and refining live financial systems that power real‑time decisions across SaaS and education portfolios.

What You Won’t Be Doing

Director Of Finance Strategy 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.

Basic Requirements

Nice‑to‑have Requirements

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things : Relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer‑facing designs. Our incubation of new businesses ranges from entirely new moon‑shot ideas to rearchitecting existing projects for today's modern cloud‑based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

Working with us

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. The compensation level for this role is $200 USD / hour, which equates to $400,000 USD / year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.

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