Cushion

Cushion AI, founded in 2016 by Paul Kesserwani, is a San Francisco-based financial technology company that has evolved its business model over time. Kesserwani, originally from Lebanon, drew upon his personal experiences with the complexities of consumer finance and a professional background that includes roles in revenue operations and product management at Twitter to establish the company.

Initially, Cushion's primary service was negotiating bank and credit card fees on behalf of its customers. Using an AI-powered bot, the platform would analyze users' transaction histories to identify various fees such as overdraft, ATM, and late fees, and then automatically negotiate with financial institutions to secure refunds. At one point, the business model involved taking a 25% cut of any refunded amounts. This service successfully secured millions in refunds for its users.

Over time, Cushion shifted its focus towards a more comprehensive bill management and credit-building solution. The company developed a platform that allows users to track, manage, and pay all their bills, including Buy Now, Pay Later (BNPL) installments, from a single dashboard. This service aims to help consumers avoid late fees and overdrafts by providing a consolidated view of their financial obligations. For a monthly subscription fee, users can access features like bill tracking, AI-powered spending insights, and calendar synchronization for payment due dates.

A key feature of the evolved platform was the introduction of a virtual card that enabled users to build their credit history. Payments made with the Cushion virtual card were reported to credit bureaus, allowing users to improve their credit scores through regular bill payments. The company has secured significant funding, raising a total of $22.5 million over several rounds, with a notable $17.4 million Series A in 2022 led by Rose Park Advisors. In early 2025, after ceasing its operations, Cushion's intellectual property and select talent were acquired by LendingClub.

Keywords: personal finance, bill management, credit builder, fintech, AI-powered finance, BNPL management, subscription management, overdraft fee negotiation, bank fee refunds, financial wellness, virtual card, credit reporting, spending insights, payment tracking, Paul Kesserwani, LendingClub acquisition, financial technology, consumer finance, bill payment, debt management, credit score improvement, automated finance