Strategic Finance Lead in Winnipeg

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 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.

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 is high. 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.

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. 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.

The team consists of 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.

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.

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.

Key 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.

Qualifications

• 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.
• 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.
• 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.
• Using AI tools to automate analytical workflows and work faster.
• Experience helping select or implement FP&A planning tooling.

Why Become a Plootonian?

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. Join Plooto and be part of a mission that matters.

Our Commitment to Inclusion

Plooto is committed to building an inclusive workplace where people of all backgrounds, experiences, and perspectives can thrive. Accommodation is available throughout the recruitment process in accordance with applicable accessibility legislation.