Strategic Finance Lead at Plooto in Remote - Canada

Job description

• 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.
• The models for your areas are rebuilt on clear drivers, with sensitivities and scenarios that leadership actually uses when making a call.
• Finance is in product and GTM decisions early enough to shape them — not brought in to forecast something already decided.
• We can trace what specific initiatives contribute against a base case, so “did that work?” has an answer.

Responsibilities

• Own driver-based financial models for the business areas you support, built around how each team actually operates.
• Embed with those teams — challenge assumptions, frame tradeoffs, and bring a return-on-investment lens to decisions before they’re made.
• Explain the why behind the numbers — investigate what moved a metric, judge whether it’s good or bad, and turn that into a recommendation. Help teams get closer to their own KPIs and the data behind them.
• Connect your models to the company plan so each area rolls cleanly into the central budget.
• Build and maintain live data pipelines — write SQL against our data warehouse (Databricks) to keep models refreshing on live data rather than manual pulls.
• Help modernize our planning infrastructure with the Senior Director — tooling, automation, or architecture.
• Distill complex analysis into crisp stories for executive and board audiences.
• Partner with the Senior Financial Analyst to keep forecasting, budgeting, and reporting coherent as Plooto scales.

Requirements

• 7+ years in strategic finance, FP&A, or business analytics — ideally in fintech, SaaS or another recurring-revenue business.
• Payments or transaction economics — take rate, transaction mix across rails, cost per transaction, and how volume converts to revenue. This is core to how Plooto makes money, and you’ll be modeling it.
• SaaS metrics in practice — ARR, MRR, churn, CAC, payback, LTV — and the judgment to know when a movement matters.
• Hands-on SQL against a warehouse (Databricks or similar) wired into Excel, building live-refresh workflows rather than static exports.
• Advanced Excel and driver-based modeling, with the ability to rebuild as the business and your understanding change.
• Comfort reasoning about cause, not just correlation — you can tell a deliberate test from a drift, ask what the hypothesis was, and judge whether a result is real.
• Exceptional communication — you can make a complex analysis simple and persuasive for technical and non-technical audiences, and hold your own with business leaders.
• A partnering instinct, and the judgment to prioritize. With fluid scope and a lot of inbound, you’ll need to decide what earns your time and say no clearly.
• Using AI tools to automate analytical workflows and work faster.
• Experience helping select or implement FP&A planning tooling.

Skills

Required

• Strategic finance
• FP&A
• Business analytics
• Payments or transaction economics
• Hands-on SQL (Databricks or similar)
• Advanced Excel
• Driver-based modeling
• Cause reasoning
• Exceptional communication
• Partnering instinct
• Judgment to prioritize

Benefits

• 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.