Flywire offers Smart Chasing, an AI system within Invoiced by Flywire that automatically selects the optimal channel, message, and timing for following up with overdue accounts based on each customer's payment history. The platform also uses generative AI to compose personalized collection messages referencing specific invoices and customer context.

Smart Chasing analyzes customer-level payment behavior and adjusts collection outreach cadences in real time, selecting among email, letter, phone, and SMS channels. High-risk accounts escalate to human collectors; accounts with clean payment histories process automatically. Separately, a generative AI feature composes personalized dunning messages tailored to specific invoices and relationship context rather than sending generic templates. Both features are part of Invoiced by Flywire, which was acquired by Flywire in August 2024.