Affirm claws back into Walmart's orbit with an exclusive Sam's Club deal. Affirm signed an exclusive, multi-year pay-over-time deal with Sam's Club on October 22, nearly two years after losing the main Walmart contract to Klarna in March 2025. Shares barely budged, closing down 1.51% at $72.40. Nineteen months after Klarna took Walmart away from Affirm, Affirm just landed Walmart's other chain, Sam's Club, as its exclusive installment partner right before the biggest shopping season of the year. Affirm announced on October 22 that it signed an exclusive, multi-year deal to become the pay-over-time provider for Sam's Club, the warehouse club chain Walmart owns. The service goes live on SamsClub.com within weeks, according to PYMNTS, with a rollout to physical club locations following in 2027. Terms of the deal were not disclosed, so there's no public number yet on what it's worth to either company. Here's the part that makes this interesting instead of routine: Walmart already picked a buy-now-pay-later partner, and it wasn't Affirm. In March 2025, Klarna announced it would replace Affirm as Walmart's exclusive BNPL provider in the US, running installment loans through Walmart's in-house fintech app OnePay. Affirm had held that Walmart relationship since 2019. Losing it wasn't a footnote. According to Affirm's own disclosures, the integrated Walmart program had made up roughly 5% of the company's gross merchandise volume and about 2% of adjusted operating income in the six months through December 2024. Affirm's stock fell as much as 8% to 11% on the day Klarna's win became public. So the Sam's Club deal reads less like new territory and more like a rematch. Walmart owns both chains, which makes this Affirm's way back into a retailer that spent a year and a half running its payments through a rival. Eligible Sam's Club shoppers will be able to apply for financing at checkout, get a real-time decision, and pick a monthly payment plan before committing, with Affirm saying as it always does that it charges no late fees and no compound interest. If this were the triumphant comeback Affirm might want it to look like, the market would have said so. It didn't. Shares closed down 1.51% at $72.40 on announcement day, according to figures reported by TIKR. That's not a rejection of the deal. It's closer to indifference, and the likely reason is that Wall Street had already priced in the Walmart loss back in 2025 and isn't ready to treat a warehouse-club contract, with undisclosed terms, as proof that the hole has been filled. Klarna's stock fell 5% to $13.94 on August 20, its second sharp drop in a week that began with a strong Q2 report and a cut full-year forecast. Affirm slipped 3% despite having already lost, then Klarna having won, the Walmart BNPL contract, while PayPal climbed 1.4% on the same day. - why klarna stock price keeps falling despite wins - buy now pay later industry stock market trends Context matters here too. Affirm's shares are down roughly 9.5% year to date in 2026, trailing a S&P 500 that's up about 7.6% over the same stretch, even as the underlying business keeps growing. Affirm's fiscal third-quarter revenue hit $1.04 billion, up 33% year over year, with gross merchandise volume up 35% to $11.6 billion and earnings per share of $0.30, well ahead of the $0.17 analysts expected. Frankly, that's a disconnect worth sitting with: a company growing GMV at 35% a year whose stock still trails the market. The Sam's Club deal is a chance to close some of that gap, not a guarantee that it will. The timing is deliberate on both ends. Launching on SamsClub.com "in the coming weeks" puts Affirm's new financing option live in time for the holiday shopping window, the single biggest volume period of the year for any BNPL provider. And the announcement lands two weeks before Affirm reports earnings on November 5, giving the company a tangible win to point to going into that call, even without a number attached to the deal's size. Klarna, for its part, has had its own rough stretch since the Walmart win. The company priced its IPO at $40 a share in September 2025 and briefly traded above $52 on debut, but the stock has since fallen hard, down to roughly $17.66 by June 2026, a decline of about 56% from its offer price as investors soured on its path to profitability. Winning Walmart didn't insulate Klarna's stock from scrutiny, and losing it didn't permanently sideline Affirm either. Both companies are still fighting for the same shoppers at the same checkout screens, just at different Walmart-owned storefronts now. What the Sam's Club deal actually proves is narrower than either company's press release suggests: Affirm found a real distribution channel inside the one retail family that had shut it out, and it got there before the holidays. Whether that's a toehold back into Walmart's full ecosystem or the extent of the comeback is a question that won't get answered until Affirm's next few earnings reports show whether Sam's Club shoppers actually use the thing. Join the discussion. No replies yet. Start the discussion. Elroy is a digital marketer and developer from Goa, with over a decade of experience web development and marketing. He has been associated with several startups and serves currently as an Editor to the Asia Pacific Industrial magazine. He occasionally writes on Startup Fortune about technology and automation.

Affirm, Sam's Club strike exclusive buy now, pay later deal. Bloomberg Tech 1 day ago 104 Affirm Holdings Inc. is teaming up with Walmart Inc.'s Sam's Club as the retailer's exclusive buy-now, pay-later partner, just weeks before the key holiday shopping season kicks off. BankBit shares this Content always with CC License Screenshot generated in real time with SneakPeek Suite

Kalepa appoints former Affirm executive Garrett Schlesinger as chief technology officer. October 22, 2026 Kalepa, an artificial intelligence technology company serving the insurance industry, has appointed Garrett Schlesinger as chief technology officer, bringing in a former Affirm engineering executive to lead its AI development and technology operations. Schlesinger joins Kalepa after spending 12 years at Affirm, where he most recently served as vice president of software engineering. He will oversee applied AI, research, engineering, data and infrastructure as Kalepa expands its technology platform and relationships with insurers globally. The appointment comes as Kalepa reports significant growth in demand for its AI-powered insurance solutions, which support underwriting, pricing, portfolio management and operational workflows. Schlesinger played a key role in developing Affirm's real-time underwriting infrastructure and scaling its technology systems as the financial technology company grew from an early-stage startup into a publicly traded business. During his tenure, he led engineering teams through multiple stages of expansion and oversaw major product initiatives, including the launch of the Affirm Card. He also directed the restructuring of core technology systems to improve scalability, performance and reliability as Affirm's transaction volumes increased. Affirm now processes more than $50 billion in annual transaction volume, according to Kalepa. "Garrett is an exceptional leader with a deep understanding of what it takes to deliver massive value from AI in production, at scale, and how to grow the teams behind it," said Paul Monasterio, co-founder and CEO of Kalepa. Monasterio said Schlesinger's experience building financial risk systems and managing engineering organizations through rapid growth will support Kalepa's next phase of development. "He brings a rare combination of technical depth, operating experience, and a proven record of scaling systems through hypergrowth," Monasterio said. Founded in 2018, Kalepa develops AI software designed for insurance carriers, managing general agents, reinsurers and program administrators. Its platform uses AI agents to execute and coordinate insurance workflows, including underwriting analysis, pricing decisions, operational processes and portfolio management. The technology is designed to integrate automated processes with human oversight, providing insurers with controls, traceability and verification capabilities for decisions involving financial and underwriting risk. As CTO, Schlesinger will be responsible for advancing the technology and data infrastructure supporting these applications while extending the platform into additional insurance functions. His experience at Affirm is relevant to Kalepa's focus on applying AI and data-driven systems to complex financial decisions, where reliability, accuracy and operational controls are important. "Kalepa is at the stage every company hopes to reach, with technology proven in production and a market ready for it," Schlesinger said. He pointed to his experience helping Affirm grow from a 12-person startup into a public company valued at more than $20 billion as preparation for his new role. "Kalepa has designed its business for the long run, and I'm looking forward to helping it scale," he said. Kalepa reported that its revenue and client count each tripled over the past year, while the number of workflows executed through its platform nearly quadrupled. The company also said it has remained cash flow positive for more than two years. Its customers include insurance companies and managing general agents such as W.R. Berkley, Bowhead and Paragon. The growth reflects increasing interest among insurers in applying AI to business processes that traditionally require substantial manual review, data analysis and specialized underwriting expertise. Kalepa's technology is intended to help insurers evaluate risks, maintain pricing discipline and improve operational efficiency while retaining human involvement in consequential decisions. Schlesinger's appointment follows several additions to the company's senior leadership team, including Chief Revenue Officer David Meister, Head of Product Audrey Howell and Head of Talent Tim Khoo-Jones. The expanded leadership team will support Kalepa's efforts to scale its operations, develop additional AI capabilities and serve a growing customer base. With Schlesinger leading its technology organization, Kalepa is positioning its engineering and research operations for further expansion as insurers evaluate broader deployment of AI across underwriting, pricing and portfolio management.