This is a remote first position for candidates based only in Canada. Olive is not in the position to sponsor work permits or visas.

Starting salary of $110,000 / year CAD + perks + stock options

About OliveOlive builds the card-linked loyalty infrastructure that powers rewards, rounding, and matching programs for some of North America's most recognizable brands. Operating on established Visa and Mastercard network partnerships, we give our customers the payment-linked loyalty capabilities they need without having to build them from scratch.

We're a flat, fast-moving team where everyone's work has a visible impact. If you like owning outcomes rather than tickets, you'll fit right in.

The RoleOlive is looking for a Financial Controller & Compliance Manager to own the company's financial operations and compliance function end-to-end. This is a hands-on, roll-up-your-sleeves role at a growing company — you won't be managing a team of analysts or delegating the close. You'll run it.

For all financial reporting responsibilities, you will report principally to our CFO — a seasoned software industry veteran with 30+ years of experience and multiple successful technology exits — who will mentor you directly as you build and scale Olive's finance function. On the Compliance Operations side, you will work with and support the senior leadership team to ensure the company's audit, security, and partner compliance obligations are met. This is a rare opportunity for a post-designation CPA to take real ownership of a company's books, reporting, and compliance posture, with direct exposure to C-suite decision-making and strategic planning.

If you're entrepreneurial-minded, comfortable wearing multiple hats, and excited by the idea of using automation and AI to make finance operations faster and more reliable — not to replace your judgment, but to sharpen it — this role is built for you.

What You'll DoFinancial Operations• Own monthly management reporting. Prepare and deliver accurate, timely management reports that give leadership a clear read on the business.

- Drive quarterly financial reporting. Produce quarterly financial statements and supporting analysis for leadership and board use.
- Manage annual budgeting and quarterly forecasting. Own the process of building the annual budget and refreshing quarterly forecasts, working closely with the CFO and department leads.
- Report quarterly to the board and senior leadership team. Present the company's financial results and performance, as well as the senior team's progress against annual and quarterly objectives.
- Manage CRA reporting and filings.



Ensure all federal and provincial tax filings and remittances are accurate and on time.
- Implement and manage international tax planning and compliance. With direction from the CFO, manage functions such as transfer pricing and US state and federal taxes.
- Own banking relationships. Manage day-to-day banking operations, cash positioning, and related administration.
- Run accounts payable. Manage supplier and partner payments, ensuring accuracy and timeliness.
- Manage expense reimbursement. Own the expense reimbursement process end-to-end, from submission through payment.
- Own the books. Maintain Olive's day-to-day bookkeeping in QuickBooks — this is a simple, well-organized environment, and we expect it to stay that way.

Compliance Operations• Own internal and external audits. Lead audit processes across SOC 2 and partner/customer compliance requirements — from readiness through to completion.

- Maintain SOC 2 posture. Own the ongoing controls, evidence, and documentation needed to achieve and maintain SOC 2 compliance.
- Manage partner compliance requirements. Ensure Olive meets the financial and compliance obligations tied to our network and channel partner agreements.

Process & Contribution• Automate where it makes sense. Identify and implement opportunities to automate accounting and finance processes using scripting tools and/or AI — you should be AI-capable, not AI-dependent, using these tools to move faster without losing command of the underlying numbers.

- Contribute beyond your lane. As part of a small, flat team, pitch in wherever you can add value to Olive's success — this isn't a role where “not my job” exists.

What You Bring• CPA designation, with 4–6 years of post-designation experience.

- Demonstrated ownership of end-to-end financial operations at a small or growing company — bookkeeping through reporting through compliance.
- Experience with (or strong working knowledge of) CRA reporting requirements for Canadian corporations; exposure to international tax matters such as transfer pricing or US tax filings is an asset.
- Exposure to audit processes — ideally including SOC 2 or similar compliance frameworks; if not direct experience, a explicit ability to pick it up quickly.




- Experience using scripting tools and/or AI to automate accounting or business processes. You know how to use these tools to work faster, and you know when to trust your own judgment over the output.
- An entrepreneurial mindset — you're energized by building a function from the ground up, not maintaining one that already exists.
- Comfort operating with a high degree of autonomy in a small, flat organization, with direct exposure to and accountability to the C-suite.
- Excellent judgment, discretion, and precision — you're handling the company's financial reality and its compliance obligations, and both demand accuracy.
- Strong communication skills — you can translate financial and compliance detail into clear, actionable information for non-finance leaders.

How You'll Be Measured• Reporting timeliness — management reports delivered within an agreed number of business days of month-end; quarterly reporting delivered on schedule.

- Budgeting and forecasting discipline — annual budget and quarterly forecasts delivered on schedule and to an agreed standard of accuracy.
- Invoice issuance timing — supplier and partner invoices issued and payments processed within target turnaround.
- Compliance performance — on-time CRA and international tax filings, SOC 2 milestones met on schedule, zero material findings on internal or external audits.
- Cash and reconciliation discipline — bank reconciliations completed within target turnaround with no unexplained variances.
- Expense reimbursement turnaround — reimbursements processed within target turnaround of submission.
- Process automation impact — number of manual finance/accounting processes automated or streamlined, and measurable time saved.

Why Olive• Direct mentorship from a CFO with 30+ years of industry experience and multiple successful technology company exits.

- Real ownership, not a seat in a large finance department — the scope of this role is genuinely yours to shape.
- A flat, fast-moving team where your work has a visible, immediate impact on the business.
- Remote-first, North America-based team.
- A fintech building on real infrastructure — Olive operates on established Visa and Mastercard network partnerships, serving customers across employee perks, dining, consumer loyalty, and fundraising verticals.

Olive Group Ltd. is an equal opportunity employer. We welcome applications from all qualified candidates.

This is a remote first position for candidates based only in Canada. Olive is not in the position to sponsor work permits or visas.

Starting salary of $110,000 / year CAD + perks + stock options

📌 Financial Controller & Compliance Manager (Canada)
🏢 Olive Fintech
📍 Canada