Strategic Finance Lead New Remote

Plooto is a Canada-born fintech company on a mission to give small and mid-sized businesses the financial power to succeed on their own terms. We make payments secure, accurate, and stress-free so businesses and their accountants can spend less time in the books, confidently manage cash flow, and make smarter decisions every day. We're a team that builds with integrity, agility, and heart, and we're looking for customer-minded pros who share our passion to join us as we scale.

About the Role

We’re hiring a Strategic Finance Lead to embed with the teams that drive our business — GTM, Product, and others as we grow — and raise the quality of decisions across the company. This is a partnering seat, not a reporting one: you’ll be in the room when a decision is being framed, not summarizing it afterward.

You’ll own the financial models for the areas you support, end to end. Because you own them, you’re in the decision rather than downstream of it. When a metric moves, your job isn’t to report that it moved — it’s to explain why, say whether that’s good or bad, and recommend what to do about it. When your business partners are weighing a decision, you’re the person quantifying the return.

You won’t inherit a playbook. You’ll write one — defining how finance partners with the business as the function grows.

The bar we’re setting

Today, a conversation about CAC often ends at “CAC went to $X because spend changed.” That’s arithmetic. We want a partner who asks the next questions: why did spend move — was it a deliberate test? What was the hypothesis, and how did it perform? How do we know our experiments are working? Is this a healthy shift or an early warning?

That’s the difference between reporting numbers and driving decisions, and it’s the heart of this role. We have good visibility into top-line trends; what we want is the ability to go a level deeper, consistently. That takes persistence — following the signal and going to find the data rather than waiting for it.

What you’ll cover

Today this role partners most closely with GTM — subscriber forecasting — and Product, where you’ll forecast TPV and revenue by product line and payment rail. As we grow, that will likely extend to Payments Strategy, Risk, and Operations.

We’ll be straight with you: we haven’t fully defined what finance support for those teams looks like yet, and we don’t expect one person to cover everything at once. Part of this job is helping us decide where finance partnership earns the most — and saying so when something should wait.

Your models serve two audiences: the teams they’re built for, and the company plan they roll into. We want models shaped to how each part of the business actually works that still connect cleanly to the central budget — so we plan from one picture instead of reconciling siloed models before a board meeting.

Build the system, not just the model

We’re not planning to solve capacity by adding people. We’d rather solve it with infrastructure: SQL pulling live from Databricks into models that refresh themselves, analysis that’s reproducible instead of rebuilt each month, and AI in the workflow where it genuinely saves time. You should be the kind of person who, faced with a manual process, gets slightly irritated and fixes it.

Much of our forecasting runs on Excel today, supported by live pipelines from our data warehouse. We know we’ll need something more scalable — and we’re deliberately open about what that is, whether a dedicated FP&A tool, a rebuild that leans harder on automation, or a different architecture altogether. You’ll help us decide and build it.

The team, and where this goes

Strategic finance is three people: the Senior Director (your manager), a Senior Financial Analyst, and you. The analyst owns the core FP&A engine — the company model, actuals, month-end performance analysis, and investor reporting. You’ll own the function-level models that feed it. You’re peers with distinct focus areas, and the expectation is that the two halves knit into one operating plan rather than running in parallel. Over time we want you cross-trained enough to cover for each other.

This is a senior individual-contributor role today, with no direct reports. We closed a funding round two months ago and are investing in growth — but we’re deliberately scaling this team through better systems and AI leverage rather than headcount. If we do add analysts, this is the person who’d oversee them. We’re not promising a management track; we’re telling you it’s a live possibility, and that the route to it is making the function work better, not bigger.

You’ll work closely with the CFO, with exposure to the CEO, and your work will feed directly into what we take to our board and investors.

What good looks like in your first year

• The model