Director of Investment Finance $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
You didn't build your expertise in PE, IB, or Big 4 M&A simply to oversee budgets and rubber-stamp presentation slides.
You're here to design, challenge, and drive forward—transforming ambiguous strategy into rock-solid execution frameworks, not multi-year projections that gather dust. You've honed your financial modeling skills under demanding conditions. Now you're ready to apply that expertise where it directly influences operating strategies, not merely investment documents. This role delivers exactly that.
Trilogy seeks a finance strategist with an operator's mindset and a dealmaker's precision: someone who excels amid uncertainty, takes ownership of results, and harnesses AI as an extension of their intellect. You'll collaborate directly with founders and senior leaders to define the trajectory of SaaS or education enterprises, constructing the financial infrastructure and investment frameworks that enable intelligent scaling without unnecessary expansion.
If your ideal workweek involves dissecting a flawed business case, reconstructing it with phased milestones and KPI safeguards, and delivering analysis that commands the attention of the executive team, this opportunity is for you.
You won't oversee 30-person departments. You won't enforce budget compliance. You won't wait years to see results. You'll craft strategy with velocity, discipline, and AI-powered accuracy, and your contributions will alter the course of ventures reshaping industries.
What you will be doing
- Constructing and maintaining 3-statement models with transparent drivers, integrated ERP data, and AI-augmented scenario analysis.
- Delivering complete investment packages—models, sensitivity frameworks, and board-ready memoranda—within 72 hours.
- Stress-testing CAC, retention, pricing, utilization, and additional metrics to establish clarity and identify critical assumptions.
- Transforming weak business plans into structured, quantifiable execution roadmaps with KPI checkpoints.
- Managing and iterating live financial systems that support real-time decision-making across SaaS and education portfolios.
What you will NOT be doing
- Managing month-end close, conducting audits, or dedicating time to compliance—this is not a controller or FP&A management position.
- Overseeing large teams or serving as a mentor—you influence through results, not staff size.
- Producing presentations that languish unread—every proposal must be supported by models, validated assumptions, and a definitive action pathway.
- Working at a leisurely pace—this is a fast-moving, AI-native, uncertainty-filled environment by intention.
- Waiting for approval to challenge convention—your mandate is to scrutinize strategy and enhance it with urgency.
Key responsibilities
Design and manage an AI-enabled financial infrastructure that informs critical investment choices, sustainable growth, and operational precision across rapidly expanding SaaS and education ventures.
Candidate requirements
- 5+ years in PE, IB, or Big 4 M&A/Corporate Finance (excluding audit/tax), with hands-on experience in deal modeling, client/board engagement, and investment evaluation.
- CPA, ACA, ACCA, CFA, CIMA, or MBA, with comprehensive understanding of US GAAP/IFRS and integrated financial statements.
- Previous experience with enterprise-grade ERP systems (e.g., NetSuite, Oracle, SAP).
- Proven application of AI as a co-pilot for modeling, scenario planning, research, memo drafting, and automation.
- History of delivering models and board-level recommendations with speed, polish, and strategic clarity.
- Located within UTC-8 to UTC+3 time zones.
Nice to have
- Familiarity with SaaS or EdTech business models.
- Experience designing financial systems, not merely modeling within existing frameworks.
- Background in ambiguous, founder-led settings with shifting priorities and direct-feedback 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.