Support Specialist, Subscriptions & Billing

ABOUT THE ROLE Cognition is building the AI software engineer of the future. As a Support Specialist focused on Subscriptions & Billing, you will own customer-facing resolution for billing, invoicing, payment, subscription, and account access issues across Cognition and Windsurf customers. This role requires excellent written communication, strong operational judgment, attention to detail, and the ability to manage sensitive customer issues with urgency and accuracy. You will help customers navigate everything from plan changes and payment failures to refunds, invoice blockers, purchase orders, renewal questions, and enterprise billing workflows. You will be the first line of response for subscription and billing issues, owning customer communication end-to-end while partnering closely with Finance, Engineering, and other internal teams to ensure issues are resolved accurately and efficiently. This is a customer-facing role with direct impact on revenue retention, customer trust, and the day-to-day experience of teams using Cognition and Windsurf. RESPONSIBILITIES - Own incoming subscription and billing issues from initial customer response through resolution, including renewals, upgrades, downgrades, refunds, payment failures, invoices, and billing-related account access. - Provide clear, empathetic, and accurate communication, especially when customers are blocked or dealing with sensitive billing situations. - Triage billing and subscription issues to determine whether they can be resolved within Support or require escalation to Finance, Engineering, or other internal stakeholders. - Partner with Finance on invoicing, purchase orders, tax/VAT questions, refunds, credits, payment reconciliations, and enterprise billing workflows. - Partner with Engineering on billing system bugs, product edge cases, account entitlements, internal tooling gaps, and subscription-related product behavior. - Track escalations to completion and keep customers updated with proactive, high-quality status updates. - Build internal playbooks, macros, tooling, and documentation that make future subscription and billing investigations faster and more consistent. Creatively apply AI tooling and agents to help improve deflection rate of billing issues. - Identify recurring ticket drivers and share actionable feedback with Finance, Engineering, Product, and Support leadership to reduce volume and improve customer outcomes. QUALIFICATIONS - 2+ years of experience in customer support, billing operations, revenue operations, customer success, account management, or a similar customer-facing operational role. - Familiarity with subscription billing platforms such as Stripe, Chargebee, or similar. - Familiarity with ticketing and customer support systems such as Zendesk, Pylon, Intercom, or similar. - Excellent written communication and customer judgment, especially when handling sensitive or high-stakes billing issues. - Strong attention to detail and ability to manage billing-related work accurately across multiple systems and workflows. - Strong organizational skills and ability to manage a high volume of concurrent tickets and escalations. - Ability to triage ambiguous customer issues, identify the right next step, and drive resolution with urgency and ownership. - Comfort working across support, billing, CRM, and internal admin tools; able to learn new systems quickly and maintain accuracy across workflows. - Ability to operate effectively in a fast-paced environment where processes, products, and tools are evolving quickly. - Interest in AI, developer tools, and the future of software engineering. NICE TO HAVE - Experience supporting enterprise customers through invoicing, procurement workflows, purchase orders, tax/VAT questions, and payment reconciliation. - Experience with refunds, credits, failed charges, disputes, proration, renewals, and other subscription billing concepts. - Experience writing help center articles, internal documentation, macros,