Senior Billing Specialist

Air is a Creative Ops System for creative teams. Our product automates the mindless tasks that creatives and marketers do every day to manage content and unlocks creativity through image recognition, automated versioning, and approval workflows. We launched in March 2021 and have raised +$70m from world-class venture capital groups including Avenir, Tiger Global, Headline Ventures, Lerer Hippeau, WndrCo, and Slack Ventures. This role requires in-office attendance at least 3 days/week in Toronto. The Role Air is hiring a Senior Support Specialist to own inbound billing support and grow into general customer support as the first hire in our Toronto CS hub. This role exists because billing support at Air requires real expertise - Stripe, enterprise payment platforms, tax exemptions, vendor forms, nuanced invoice questions - and we need someone who can take full ownership of that inbox without relying on escalation. Before flagging an issue, you've already pulled the Stripe record, Mode account, and any relevant Slack/Intercom history. You come with context, not questions. At the same time, we're building out CS capacity in Toronto, so this role has room to grow into broader customer support responsibilities over time. Because you'll be our first hire in Toronto, 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'll be the person customers and internal teams rely on when something billing-related needs to get resolved now. You're AI-native - you use tools to gather context fast, work through complex billing histories independently, and close tickets without hand-holding. You know to verify who you're talking to before making account changes, and you don't let urgency from a customer override that check. You take satisfaction in a clean inbox and a well-resolved issue. You have strong written and verbal communication, including on difficult calls/emails. You're composed under pressure, clear without being robotic, and know how to move a conversation toward resolution — whether that's a frustrated customer disputing an invoice or a past-due account that's been avoiding your messages. This is not a strategy or process-design role. It's for someone who has done this before, picks up context quickly, and gets things done. Core Responsibilities Billing Support (Core) 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 General Customer Support (Stretch) 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 Requirements 2-4 years in billing support, accounts receivable, payments support, or a closely related customer-facing role - you've worked a real billing inbox and don't need a long ramp 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 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, writing saved replies, using checklists + step-by-step guides to stay consistent under high pressure and volume Clear, professional written communication. You're often the bridge between a frustrated customer and a complex backend process - tone and clarity matter Strong judgment. You know what to fix now, what to flag, and what to document for next time How We Work at Air Act like a driver : Take initiative and ownership without waiting to be told. Work in public : Share ideas openly, get feedback early, and collaborate across teams. Play to win : Aim high and bring creativity, adaptability, and focus to your work. Say the hard thing : Give and receive feedback with clarity and respect. Disagree and commit : Debate honestly, then align quickly to move forward together. Benefits Why Air? Growth and Impact: Join a rapidly scaling company with a mission to transform the creative ops space. Your work will have a direct, tangible impact on our ARR growth. Comprehensive Benefits: We offer competitive medical, dental, and vision insurance, along with dependent coverage. You’ll also enjoy a generous work-from-home stipend, professional development reimbursement, and unlimited vacation days. Commitment to Diversity: We believe in the power of diverse perspectives and strive to create an inclusive culture that welcomes individuals from all backgrounds and experiences. Competitive Compensation: The base salary for this position in Toronto is between CAD $62,000 - $100,000 + equity, commensurate with experience. At Air, we’re committed to building a world-class team and helping every individual reach their full potential. If you're passionate about solving big problems and growing with an innovative company, we’d love to meet you!