Senior Billing Lead: Stripe & AR Operations

Monograph; Toronto; Hybrid; CAD 62,000 - 100,000; Full time

Job summary

Air is hiring a Senior Billing Specialist to own our billing operations end to end in Toronto. This role focuses on Stripe administration, accounts receivable, enterprise vendor platforms, and tax exemption processing.

You will be the primary billing contact with customers, but the core work is accounting and billing operations, reconciliation, and ensuring accuracy in invoices and payments.

Qualifications

• Billing / AR / accounting background (2-4 years).
• Fluency with Stripe and payment processing.
• Experience with enterprise billing platforms like Bill.com, Tipalti, Coupa or Ariba.
• Ability to use AI-native workflows to gather context and draft responses.
• Strong ownership and process discipline under high volume.
• Clear, professional written communication.

Responsibilities

• Own the billing inbox and triage inquiries via Intercom and email.
• Execute Stripe operations: subscriptions, refunds, invoices, credits, updates.
• Manage enterprise billing workflows and vendor enrollment.
• Handle tax exemption setup and certificate collection.
• Verify vendor payment details before releasing funds.
• Investigate disputed invoices and provide explanations to customers.
• Occasional CX tickets handling and help center contributions.

Skills

Billing/AR

Financial fluency

Stripe fluency

Communication

Problem solving

Tools

Bill.com

Tipalti

Coupa

Ariba

Job description

Air is hiring a Senior Billing Specialist to own our billing operations end to end in Toronto. This role focuses on Stripe administration, accounts receivable, enterprise vendor platforms, and tax exemption processing.

You will be the primary billing contact with customers, but the core work is accounting and billing operations, reconciliation, and ensuring accuracy in invoices and payments.