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ᓄᓇᕗᑦ Nunavut, Canada
Remote only
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.
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.
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.
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.
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.
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.
If you're looking to make a meaningful impact, look no further. We're transforming the payments space in North America by delivering an unrivalled product experience to solve a real and pressing problem for SMBs.
The biggest reason small businesses fail is poor financial management and cash flow — and Plooto fixes that. We have strong product-market fit, a massive opportunity ahead, and the backing of experienced fintech leaders.
You'll join a team that cares deeply about customer impact, takes pride in our craft, and moves with urgency. We're just getting started — and you'll help shape the next chapter of our growth story.
Join Plooto and be part of a mission that matters.
Plooto is committed to building an inclusive workplace where people of all backgrounds, experiences, and perspectives can thrive. We know great teams are built through diverse thinking, and we encourage you to apply even if your experience does not align perfectly with every qualification listed.
Accommodation is available throughout the recruitment process in accordance with applicable accessibility legislation. If you require accommodation at any stage, please let us know—we’re happy to work with you.
This posting is for one available position. Compensation will be determined based on the successful candidate’s knowledge, skills, experience, and overall alignment with the role.
