About this role.
Tremendous is hiring a Head of Finance to lead a finance function centered on FP&A, strategic finance, and financial storytelling for a profitable, fully remote payouts platform. The role dedicates roughly 75% of its scope to core FP&A, including complex revenue modeling, scenario planning, forecasting, and automation. The remaining work includes enterprise deal pricing and structuring, performance analysis, external financial narratives, and eventually building the finance team. This is a hands-on leadership role for a startup finance operator who can work effectively with incomplete information and partner closely with data, sales, legal, product, and executive leadership.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would begin by defining the economic drivers for each revenue stream, such as customer cohorts, transaction volume, pricing, take rate, payout mix, and variable costs. I would create a documented driver-based model with separate assumptions, operating metrics, P&L outputs, cash implications, and base, upside, and downside scenarios. I would then establish a regular actuals-to-forecast cadence and automate data ingestion and variance reporting where reliable source data is available.
I would evaluate expected volume, pricing structure, implementation requirements, contribution margin, variable processing costs, service levels, contractual risk, and strategic value. I would model the deal under realistic utilization and downside assumptions, identify negotiation guardrails such as minimum margin or commitment levels, and clearly communicate trade-offs to sales, legal, and leadership. The goal is to support commercial flexibility without accepting economics that erode long-term value.
I tailor the message to the decision required rather than presenting every available metric. I lead with the key conclusion, quantify the drivers and risks, use a small number of clear visuals or scenarios, and connect financial outcomes to operational actions. I also document definitions and assumptions so stakeholders can understand the analysis and challenge it constructively.
In a fast-moving environment, I first identify which unknowns could materially change the decision and which can be estimated with reasonable assumptions. I build a decision-oriented range of outcomes, seek rapid input from relevant owners, and recommend a path with explicit guardrails and a review date. This enables progress while making the uncertainty transparent and ensuring the decision can be adjusted as better data arrives.
I would first assess the current model, reporting cadence, data quality, close process, forecast accuracy, and key decision points across the company. Next, I would align leadership on a common set of operating metrics, establish forecast ownership and scenario-planning processes, and identify the highest-value automation opportunities. By the end of the period, I would aim to deliver a trusted planning rhythm, a prioritized finance roadmap, and clear recommendations for team structure and controls as the company scales.
Tremendous is the global platform built for businesses to send thousands of payouts to anyone, anywhere, for free. We’re trusted by 20,000 organizations like Atlassian, MIT, and United Way to deliver gift cards and money to millions of recipients worldwide.
Our customers (researchers, marketers, HR teams, nonprofits, and platform businesses) rave about how fast and easy Tremendous is to use. Check out our ratings on G2.
Tremendous is profitable and growing without outside investors. We’re a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life. The team agrees– our employee NPS is in the high 80s.
About the role
As the Head of Finance, you will sit at the intersection of operational modeling, data-driven strategy, and narrative storytelling. This is a high-leverage role reporting directly to leadership, where your time is split is between roughly 75% core FP&A and 25% strategic finance.
You will be responsible for translating the operational complexity of our business into clear, defensible financial forecasts, while simultaneously building compelling financial narratives for internal decision-making and external stakeholders. We are profitable and growing without outside investors, meaning your time will be spent on actual business strategy and execution rather than investor relations or board presentation theater
What you’ll do
Own FP&A: Oversee and maintain detailed financial models that capture our complex revenue streams. Work with the Finance and Data teams to document assumptions, outputs, and scenarios in a way that’s both rigorous and understandable.
Drive forecasting and planning: Keep our financial forecasts updated, accurate, and defensible. Automate wherever possible.
Support deal desk: Help structure and price of complex enterprise deals. Work cross-functionally with sales, legal, and product to ensure deals are both financially sound and aligned with our strategic goals.
Explore and optimize: Dig into our data to identify trends, inefficiencies, and opportunities. Bring curiosity and analytical rigor to everything you do.
Create the external story: Package our business model and financials into clear, compelling narratives for external parties- whether that’s potential strategic partners, vendors, or long-term stakeholders.
Build the function: As we grow, you’ll have the opportunity to build out the finance team and establish best practices for financial operations.
About you
4+ years at growth-stage startups: You’ve led finance teams and owned the FP&A model at fast-moving startups and understand the pace and ambiguity that comes with it. You’re comfortable making decisions with incomplete information.
Strategic finance perspective: You can think about the business from a strategic angle and tell a compelling financial story, not just produce the numbers.
Modeling obsessive: You genuinely enjoy building financial models and can get lost in Excel or other modeling tools. You care about getting the details right.
Deal structuring experience: You’ve worked on pricing and structuring complex enterprise deals, ideally in a B2B context.
Transaction involvement: Hands-on involvement in startup transactions (investment or acquisition).
Naturally curious: You ask “why” and “what if” constantly. You’re drawn to complex problems and enjoy digging into data to find answers.
Low ego, high impact operator: You’re excited to do the work yourself rather than delegating everything.
What’s cool about the role
No board theater: We’re profitable with no outside investors, which means no board meetings and no wasted time on investor relations. Your work will focus on actual financial planning and analysis.
Complex, interesting business: Our revenue model is sophisticated and multi-faceted. If you like easy, simple SaaS businesses, this isn’t the role for you. If you like intellectual challenges, you’ll love it here.
Competitive pay and equity. Base salary for this role: $250,000 to $290,000.
Real benefits. 100% covered health (US), unlimited PTO, 12-16 weeks paid parental leave.
Fully remote. Work from anywhere in the Americas.
Great culture. Read more about how we work in our public handbook.
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