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Job summary

Build and own the finance and compliance functions, including monthly management reporting, CRA filings, and banking relationships. Lead the end-to-end SOC 2 compliance process and automate accounting workflows using AI and scripting tools.

Job details

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

What you’ll do

Build and own the finance and compliance functions, including monthly management reporting, CRA filings, and banking relationships. Lead the end-to-end SOC 2 compliance process and automate accounting workflows using AI and scripting tools.

Requirements

Requires a CPA designation with 4-6 years of post-designation experience and hands-on SOC 2 implementation experience within a company. Must have a background in startup environments and be legally entitled to work in Canada.

Listed skills

• Financial Reporting · Preferred
• Bookkeeping · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• Financial Controlling
• SOC 2 Compliance
• Cross-border Payments
• CRA Reporting
• QuickBooks
• Financial Reporting
• Bookkeeping
• Audit Management
• Process Automation
• Cash Positioning
• Accounts Payable
• Reconciliation

Job areas

• Finance & Accounting
• Management & Leadership
• Technology
• Software
• Legal