Original job description
About Olive
Olive builds the card-linked loyalty infrastructure behind 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 payment-linked loyalty capabilities without having to build them from scratch. We serve customers across employee benefits, dining, consumer loyalty, and fundraising including US enterprise clients.
We're a small, flat team. Everyone owns outcomes, not tickets.
The Role
We're hiring a Financial Controller & Compliance Manager to build and own Olive's finance and compliance function.
Own is the operative word. This function doesn't exist in a finished form yet. You'll be creating the processes, not inheriting them, and you'll have room to bring in the tools and outside expertise you need to do it. You'll work directly with our CFO and the rest of the leadership team, who'll back you on the decisions that matter but the day-to-day design of how finance runs here will be yours.
Is This the Right Fit?
Startup or small-company experience. You've worked somewhere fast-moving and under-resourced, where processes were still taking shape and you were comfortable figuring things out without a playbook handed to you. You know how that differs from a structured finance department and you prefer it.
Hands-on SOC 2 experience. You've built, maintained, or carried a company through SOC 2 from the inside. This isn't something you'll be overseeing from a distance including the controls, evidence, documentation, and auditor relationships sit with this role.
Cross-border payments exposure. Olive operates a US entity and moves money across the border for US clients. Reconciling cross-border reward payments and payouts is part of the day-to-day, and experience with a rewards or rebate model is a real advantage.
What You'll Own
Financial operations
Monthly management reporting: accurate, on time, and useful to leadership
Quarterly financial statements and supporting analysis for leadership and board
CRA reporting and filings, federal and provincial, including remittances
Reconciliation of reward payments: matching program funding, network settlements, and merchant/partner payouts, including cross-border flows, and resolving variances
Banking relationships, cash positioning, and related administration
Accounts payable: supplier and partner payments
Expense reimbursement, end to end
Day-to-day bookkeeping in QuickBooks (a simple, well-organized environment we intend to keep that way)
Compliance
SOC 2: ongoing controls, evidence, documentation, and audit readiness
Internal and external audits across tax, SOC 2, and partner/customer requirements
Financial and compliance obligations tied to our network and channel partner agreements
Process
Automate where it makes sense, using scripting and/or AI to cut manual work. We want someone who's AI-capable, not AI-dependent. These tools should sharpen your judgment, not stand in for it.
Contribute beyond your lane. On a team this size, "not my job" doesn't come up.
What You Bring
Required
CPA designation with 4–6 years of post-designation experience
Hands-on SOC 2 experience gained inside an operating company
Experience owning finance at a startup or small, fast-growing company: bookkeeping through reporting through compliance, with you as the person doing it
Working knowledge of CRA reporting requirements for Canadian corporations
Experience using scripting tools and/or AI to automate accounting or business processes
Comfort with a high degree of autonomy, direct C-suite exposure, and direct accountability
Excellent judgment, discretion, and precision
Strong communication: you can translate financial and compliance detail into clear, actionable information for non-finance leaders
Legally entitled to work in Canada and Canada-based (this is a Canada-only hire)
Nice to have
Fintech, payments, or SaaS experience
Exposure to other compliance frameworks (ISO 27001, PCI DSS)
Exposure to cross-border payments and reconciliation: reward, rebate, cashback, or similar payouts flowing between multiple parties
How You'll Be Measured
Reporting timeliness:** management reports within an agreed number of business days of month-end; quarterly reporting on schedule
Compliance performance: on-time CRA filings, SOC 2 milestones met on schedule, zero material findings on internal or external audits
Invoice and payment turnaround: supplier and partner invoices issued and payments processed within target
Cash and reconciliation discipline: bank and reward payment reconciliations completed within target turnaround with no unexplained variances
Expense reimbursement turnaround; processed within target of submission
Automation impact: manual processes automated or streamlined, and measurable time saved
