--- title: 'Strategic Finance Lead at Plooto' canonical: 'https://feeny.ai/job/strategic-finance-lead-plooto-canada-daqa69fyc4zg' type: 'job' last_seen: '2026-10-20' --- # Strategic Finance Lead at Plooto - **Company:** Plooto - **Location:** Canada - **Work type:** remote - **Posted:** 2026-09-24 - **Last confirmed live:** 2026-10-20 - **Apply:** https://job-boards.greenhouse.io/plootocareers/jobs/5433788008 ## Job description ## About Plooto 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 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. ## 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. 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. 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. 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. Our Commitment to Inclusion 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. ## About Plooto ## Company Overview - **One-liner**: Plooto is an all-in-one payment automation platform that helps small and midsize businesses and their accountants streamline accounts payable and receivable in one secure, easy-to-use solution. - **Entity Type**: Private (Series B) - **Headquarters**: Toronto, Ontario, Canada - **Founded**: 2015 - **Founders**: Serguei Kloubkov (Co-Founder & Co-CEO), John McLane (CEO) ## Core Business - **Primary industry/industries**: Financial Services, Fintech, Payment Automation - **Target customers**: Small and Midsize Businesses (SMBs), Accounting Firms, Bookkeepers - **Mission or purpose statement**: To put businesses in control of their finances so they can build the future of their dreams. ## Products & Services - **Accounts Payable (AP) Automation**: Automates the entire bill payment process, from invoice receipt to approval and payment execution. Includes custom approval workflows, two-way sync with accounting software (QuickBooks, Xero, NetSuite), and real-time payment tracking. - **Accounts Receivable (AR) Automation**: Automates the invoicing and collections process, sending invoices, collecting payments, and syncing back to accounting software for full cash flow visibility. - **International Payments**: Facilitates cross-border payments with competitive exchange rates, clear fees, and built-in compliance for paying international vendors. - **Payment Options**: Supports EFT/ACH, credit card, foreign exchange, and instant payments via a pre-funded Plooto Instant account. - **Accounting Software Integration**: Two-way sync with QuickBooks, Xero, and NetSuite for seamless reconciliation and data entry reduction. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed - **Key Metric**: Annual Revenue of $35.0M (USD) and Total Funding of $29.4M (USD) - **Notable Investors/Partners**: Centana Growth Partners (led Series B), FINTOP Capital (led Series A). Key integrations with QuickBooks, Xero, and NetSuite. - **Growth Signals**: Supports 14,000+ businesses, processes 3.2M+ transactions annually, has grown headcount 5.6% year-over-year to 81 employees, and has a presence in Canada, the United States, India, and the United Kingdom. ## Competitive Advantages - **Deep Accounting Integration**: Two-way sync with QuickBooks, Xero, and NetSuite creates a sticky ecosystem for accounting firms and their clients, reducing manual data entry and errors. - **Unified AP & AR Platform**: Combines both accounts payable and receivable in a single platform, offering a complete cash flow management solution that competitors often split into separate tools. - **Customizable Approval Workflows**: Provides granular control over payment approvals, reducing firm risk and ensuring compliance, which is a critical need for accounting firms. - **Built-in Compliance for International Payments**: Simplifies complex cross-border payments with transparent fees and regulatory compliance, a key pain point for SMBs. ## Strategic Focus - **Deepening Accounting Ecosystem**: Continuing to strengthen integrations with major accounting platforms (QuickBooks, Xero, NetSuite) to become the default payment layer for accounting firms. - **Product Expansion**: Building out a more complete cash flow management platform that unifies payments, processes, control, reconciliation, and reporting. - **Scaling Customer Base**: Growing beyond 14,000 businesses by expanding sales and marketing efforts, particularly in the US and international markets. - **International Growth**: Expanding presence in the United States, India, and the United Kingdom to capture a larger share of the global SMB payment market. ## Why Work Here - **Meaningful Impact**: Employees directly shape how thousands of businesses run and grow, with a clear mission to empower SMBs. - **Growth Opportunities**: The company invests in learning and development, and the fast-growing fintech environment offers career advancement. - **Inclusive Culture**: Celebrated diverse perspectives, with 86% of employees rating it a great place to work (vs. 60% at a typical company) according to Great Place to Work® Canada. - **Flexibility and Balance**: Supports hybrid and remote-friendly ways of working, with many roles listed as "Remote - Canada" or "Remote - India." - **Forward Momentum**: Part of a fast-growing fintech that is constantly evolving, with a clear product roadmap and international expansion. - **Engineering Culture**: The engineering team is a core part of the business, with a Senior Backend Engineer role currently open. The company values data-informed learning and taking smart risks. - **Hiring Process**: A structured 4-step process: Screening interview → Take-home or on-call case study → Final interview → Reference & background checks → Offer. ## Sources 1. [plooto.com](https://www.plooto.com/) 2. [plooto.com/careers](https://www.plooto.com/careers) 3. [job-boards.greenhouse.io](http://job-boards.greenhouse.io/plootocareers) 4. [greatplacetowork.ca](https://www.greatplacetowork.ca/en/certified-company/z4870188000002257001) 5. [linkedin.com](https://ca.linkedin.com/company/plooto) ## Other roles at Plooto - [Account Executive, Channel Sales](https://feeny.ai/job/account-executive-channel-sales-plooto-canada-jc8a8kjrrf7n) — Canada - [Senior Accountant](https://feeny.ai/job/senior-accountant-plooto-canada-jyhgrr96akz1) — Canada - [Director, Growth Marketing](https://feeny.ai/job/director-growth-marketing-plooto-canada-5a4vgt502vet) — Canada - [Vice President, Commercial Growth](https://feeny.ai/job/vice-president-commercial-growth-plooto-canada-tdg04h1469z2) — Canada - [Senior Backend Engineer](https://feeny.ai/job/senior-backend-engineer-plooto-canada-4pjhyt1zsmvm) — Canada - [Account Manager, Direct Sales](https://feeny.ai/job/account-manager-direct-sales-plooto-india-x6js9eqyds78) — India - [Enterprise Customer Success Manager](https://feeny.ai/job/enterprise-customer-success-manager-plooto-toronto-ontario-canada-fjraqh0ba9aq) — Toronto Ontario Canada, India - [Manager, Privacy & Regulatory Compliance](https://feeny.ai/job/manager-privacy-regulatory-compliance-plooto-canada-cmv2q7kbtb9v) — Canada - [Decision Scientist, Risk](https://feeny.ai/job/decision-scientist-risk-plooto-canada-bw5x1rs2kqb9) — Canada - [Senior Manager, Event Marketing](https://feeny.ai/job/senior-manager-event-marketing-plooto-canada-r04dn6j1eec4) — Canada