AI-First Finance Specialist | Payments, Risk & Automation

AI-First Finance Specialist | Payments, Risk & Automation
CapeShore Group  •  Well-Funded Startup  •  Full-Time, Permanent  •  Remote (BC or Ontario)

Build the AI-powered finance function of a growing payments business.

If you have ever thought “this reconciliation should run itself,” this is the role to build it. CapeShore is a well-funded startup building Merchant of Record businesses for e-commerce and telehealth. We want a hands-on finance professional who combines sharp financial judgment with AI, automation and payment operations. You will help design the systems, not just operate them.

What you’ll own

• Reconcile transactions across payment processors, merchant IDs (MIDs), banks and merchants, including fees, reserves, refunds and chargebacks.
• Build AI-assisted reconciliation workflows, exception alerts and chargeback and reserve dashboards.
• Own month-end close, merchant liabilities, settlement accuracy, cash forecasts and multi-entity reporting.
• Turn payments data into clear profitability and risk insights for leadership.
• Automate repetitive finance work with AI, SQL, Python or scripts, while validating every result against source records.

What you bring

• 4+ years in finance, accounting or payment operations, with hands-on responsibility for financial reconciliations and controls.
• Experience reconciling card, processor, marketplace, wallet or other transaction data to bank settlements.
• A real example of finance automation you personally built using AI and SQL, Python, scripts or similar tools.
• Sound judgment around refunds, chargebacks, reserves, exposure and payout controls.
• CPA, subscription billing and payment-acquiring experience are advantages, not prerequisites.

Why join CapeShore?

• Excellent base salary + performance bonus.
• Real ownership and direct access to decision-makers in a well-funded startup.
• Freedom to build better AI and automation tools, with room to grow into finance and payments-risk leadership.

How we hire
A short application, two practical written examples, a paid skills exercise for finalists and a leadership interview.We use AI tools to help screen and assess applications. People make the hiring decisions. This is an existing vacancy. Accommodation is available on request during recruitment.