Senior Billing Specialist

Air • Toronto, ON

46d • CA$62,000 - CA$100,000 • Hybrid

About The Position

Air is hiring a Senior Billing Specialist to own our billing operations end to end: Stripe administration, accounts receivable, enterprise vendor platforms, tax exemption processing, and invoice reconciliation. This is an accounting and finance-operations role first. You'll also be the person customers talk to when something billing-related needs to get resolved — but that customer-facing piece is secondary to your ability to run billing operations with precision and independence.

This role exists because billing at Air requires real financial expertise: Stripe fluency, AR reconciliation, enterprise payment platforms (Bill.com, Tipalti, Coupa, Ariba), tax exemption compliance, and vendor payment verification. Before flagging an issue, you've already pulled the Stripe record, reconciled it against Mode, and reviewed the relevant history. You come with context, not questions.

To be clear: this is not a general customer support or customer success role. You'll occasionally explain an invoice, resolve a dispute, or verify an account change directly with a customer — but the core of the job is accounting and billing operations work: reconciliation, Stripe administration, tax compliance, and vendor management. If your background is primarily in support/CS ticket queues without hands-on billing, AR, or bookkeeping experience, this role isn't the right fit.

You're the first Support team hire in our Toronto CS hub, so you need to operate independently from day one. We'll set you up with process, tooling, and context, but you'll own the inbox without someone looking over your shoulder. You take satisfaction in a clean inbox, a reconciled ledger, and a well-resolved billing issue.

You have strong written and verbal communication for the moments that require it — a frustrated customer disputing an invoice, or a past-due account that's been avoiding your messages. But this isn't a communication-first role: it's for someone who has done real billing/AR work before, picks up financial systems and context quickly, and gets things done without hand-holding.

Requirements

• Billing / AR / accounting background (2-4 years). You've worked a real billing or accounts receivable seat - reconciliation, invoicing, collections, or payments operations - not just a support ticket queue
• Financial fluency. You understand how invoices tie to a ledger, what AR aging means, and how to reconcile a payment processor against internal records
• Stripe fluency. You can find a customer, cancel a subscription, issue a refund, void an invoice, update a payment method, and apply a coupon without needing guidance
• Enterprise platform familiarity. Experience with Bill.com, Tipalti, Coupa, or Ariba - or a clear track record of picking up new financial tools fast
• AI-native workflow. You use AI tools in your daily work to gather context, draft responses, and resolve ambiguous situations without escalation
• Process ownership. You actively build your own systems, working with templates, saved replies, and checklists to stay consistent under high pressure and volume
• Clear, professional written communication. You can act as the bridge between a frustrated customer and a complex backend process when needed - tone and clarity matter in those moments
• Strong judgment. You know what to fix now, what to flag, and what to document for next time

Responsibilities

• Own the billing inbox. Triage and resolve inbound inquiries across invoice questions, unexpected charges, payment failures, subscription disputes, and cancellation requests - via Intercom and email inboxes
• Execute Stripe operations. Process subscription changes (cancellations, plan downgrades, seat changes), issue refunds, void and reissue invoices, apply credits and coupons, update payment methods, and retry failed charges
• Manage enterprise billing workflows. Complete vendor enrollment forms (Bill.com, Tipalti, Coupa, Ariba); reconcile incoming payments against open Stripe invoices; maintain platform credentials and workflows
• Handle tax exemption setup. Collect certificates from qualifying non-profit and university customers, upload to AvaTax/Avalara ECM, and apply correct discount codes and exemption adjustments in Stripe
• Verify vendor payment details. Confirm bank details and invoice legitimacy via phone before releasing funds - you understand why email alone isn't sufficient
• Investigate disputed and confusing invoices. Coordinate with the relevant AE or CSM to resolve billing edge cases; generate clear, accurate written explanations for customers
• Handle general CX tickets during billing downtime - product questions, access issues, account management
• Contribute to the help center and internal runbooks as recurring billing patterns surface
• Route non-billing tickets appropriately; collaborate cross-functionally with Product, Engineering, and Revenue as needed

Benefits

• Competitive medical, dental, and vision insurance, along with dependent coverage
• Generous work-from-home stipend
• Professional development reimbursement
• Unlimited vacation days

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed