Director of Finance Strategy $400,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
Your experience in PE, IB, or Big 4 M&A wasn't meant for budget maintenance and deck approvals.
You're here to design, challenge, and drive momentum — transforming ambiguous strategy into robust execution frameworks, not multi-year projections that collect dust. You've proven your ability to build financial models in high-pressure environments. Now you're ready to deploy that expertise where it directly influences operating decisions, not just pitch books. This role delivers that opportunity.
Trilogy seeks a finance strategist with operational instincts and dealmaker precision: someone who excels in uncertainty, takes ownership of results, and uses AI as a force multiplier. You'll partner directly with founders and senior leaders to define the future of SaaS or education businesses, creating the financial infrastructure and investment logic that enable intelligent scaling, not unchecked growth.
If your ideal workweek involves dissecting a flawed business case, reconstructing it with phased milestones and KPI boundaries, and delivering a memo that commands executive attention, this is your opportunity.
You won't be overseeing large finance teams. You won't be enforcing budget compliance. You won't be waiting years to see impact. You'll be influencing strategy with velocity, discipline, and AI-augmented rigor, and your contributions will redirect ventures that are reshaping industries.
What you will be doing
- Constructing and maintaining 3-statement models with transparent drivers, integrated ERP data, and AI-powered scenario analysis.
- Delivering complete investment packages — financial models, sensitivity frameworks, and board-ready documentation — within 72 hours.
- Stress-testing CAC, retention, pricing, utilization, and similar metrics to generate insight and expose critical assumptions.
- Transforming weak business plans into structured, trackable execution roadmaps supported by KPI thresholds.
- Managing and evolving live financial platforms that enable real-time decision-making across SaaS and education portfolios.
What you will NOT be doing
- Managing month-end close, audit filings, or compliance workflows — this is not a controller or FP&A management position.
- Building or supervising large teams — your influence comes from deliverables, not org charts.
- Producing presentations that go unread — every proposal must be supported by rigorous models, validated assumptions, and a clear decision framework.
- Working at a predictable pace — this is a fast-moving, AI-native, high-ambiguity environment by intention.
- Waiting for approval to challenge convention — your mandate is to scrutinize strategy and sharpen its execution.
Key responsibilities
Design and manage an AI-enhanced financial infrastructure that supports high-impact investment decisions, scalable expansion, and operational precision across rapidly growing SaaS and education ventures.
Candidate requirements
- 5+ years in PE, IB, or Big 4 M&A/Corporate Finance (not audit/tax), with direct involvement in deal modeling, client/board engagement, and investment decisions.
- CPA, ACA, ACCA, CFA, CIMA, or MBA, with strong command 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.
Nice to have
- Exposure to SaaS or EdTech business models.
- Experience architecting financial systems, not just modeling within them.
- Prior experience in ambiguous, founder-led environments with evolving scope and high-candor cultures.
Meet the hiring manager
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.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
Frequently asked questions
About the role
Reviews
Meet some people who've landed similar jobs
Recruitment sucks. So we’re fixing it.
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
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
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.
Join the world's largest community of 
AI-first remote workers.