A tale of two innovations: Square’s AI edge for SMBs and Morgan Stanley’s code makeover

    From payments to investments: The divergent paths of AI transformation


    It’s a new week of the 10Q edition, and the conversation around AI isn’t slowing down. And judging by the pace of innovation, companies are in no mood to rest. 

    We track two new AI developments this week from well-known public companies: Square, the payments and commerce unit of Block, and legacy bank Morgan Stanley.

    AI In Payments: How Square’s Conversational AI Assistant signals a shift in SMB tech — and why it matters

    Square has introduced a conversational AI assistant, Square AI, to help sellers by answering questions about using Square’s business technology platform and providing insights into their own business trends.

    In a time when nearly every company is racing to slap AI onto a product label, Square’s latest move feels different, not because it’s more technically sophisticated, but because it directly addresses a chronic pain point for small business owners: decision paralysis in the face of complexity.


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    How Pagaya (PGY) and Upstart (UPST) are venturing deeper into AI to make fintech lending more intelligent

      Fintech lending dives deeper into the algorithm age


      Wall Street loves a good buzzword, but when AI appears on quarterly earnings calls and product roadmaps, it’s not just talk – it’s a pivot. Over the past week, some of the non-headline-grabbing public financial firms have moved their advanced AI efforts into production, beyond the lab phase and into frontline operations. 

      We look at how Pagaya and Upstart fit into today’s narrative, which goes beyond their AI initiatives to focus on how they are operationalizing those efforts and gradually integrating AI into their company architecture.

      Pagaya’s AI engine is now powering a $300 million BNPL push

      For anyone watching the mechanics of modern consumer finance, Pagaya is making an effort to become one of the critical AI players in the lending world.

      Founded in Israel and listed on the NASDAQ [PGY], Pagaya built its name on a very particular skill: using artificial intelligence to underwrite “second-look” loans, the kind traditional lenders might decline at first glance. The company’s bread and butter is partnering with financial institutions that want to expand credit access without eating a mountain of risk. Its AI models pore over alternative data and make fine-tuned credit decisions that don’t rely solely on FICO scores.

      Recent AI developments

      i) BNPL Bond Issuance: In the past week, Pagaya made a big move: it issued a $300 million bond backed by buy now, pay later (BNPL) loans, a first for the company. It did this in partnership with Klarna, the Swedish BNPL giant that’s been revamping its financials ahead of a possible IPO. The bond deal, arranged by J.P. Morgan Chase and Apollo’s Atlas, gives Klarna more flexibility to offload credit exposure while allowing Pagaya to flex its AI muscle in a hot but volatile space. The bond was oversubscribed and included AAA-rated tranches yielding about 1.75 percentage points above Treasury bonds, indicating strong investor demand despite higher risk premiums compared to competitors like Affirm.

      What makes this interesting is that Pagaya is applying its AI underwriting system to a new frontier, point-of-sale financing, where risks are nuanced, margins are thin, and speed is everything. Klarna handles the consumer touchpoints; Pagaya, behind the curtain, crunches the credit decisions and helps get the funding flowing.

      ii) Asset-Backed Securities (ABS) Issuances: This isn’t Pagaya’s first rodeo in asset-backed securities…

      What we’re seeing now is Pagaya expanding its model, not pivoting. The BNPL-backed bond is less about jumping on a trend and more about applying its proven tech stack to an adjacent product, one that’s booming in retail but increasingly scrutinized for risk.


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      Remitly’s Q1 in review — and why its WhatsApp integration could be a turning point for fintech UX

        A conversation on Remitly’s financial performance, platform integration, & conversational AI developments


        The tech world loves a good shake-up story, especially when it comes to payments. But when the goal is only to upend an industry, things can get lost in translation. While speed and innovation are great, and one of the essential aspects of payments, for many, even small barriers to sending money can feel like an insurmountable challenge. That’s the market Remitly has focused on. The payments firm is solving a more fundamental problem — how to make sending money home a little more predictable, a little less frustrating.

        Earlier this month, Remitly shared its Q1 2025 financial results. First quarter revenue was $361.6 million, up 34% YoY, and active customers increased to over 8 million, up 29%. 

        A week before its earnings release, the company announced its integration with WhatsApp. Through WhatsApp, Remitly users can send, monitor, and control their international transfers without downloading another app. Remitly’s goal isn’t necessarily to get users to only use the app — it’s to keep them in the Remitly ecosystem, regardless of channel.

        I spoke with Matt Oppenheimer, co-founder and CEO of Remitly, to discuss the Q1 earnings highlights, and with Ankur Sinha, Chief Product and Technology Officer, to learn more about the new WhatsApp integration and what this launch signals about the future of remittances and fintech UX.

        We also explore the role of Remitly’s conversational AI in enabling users to send money directly within WhatsApp, check live exchange rates and fees before sending, and track transfers — all while receiving support in a single conversation thread.

        Matt Oppenheimer, Co-Founder and CEO, Remitly

        Q: What key strategies contributed to Remitly’s Q1 2025 positive outcome?

        Matt Oppenheimer: Our strong Q1 results reflect the compounding effect of three core drivers: 


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        Affirm and Robinhood’s Earnings: The story so far and the road ahead

          The growth paths of 2 fintechs through their recent quarterly earnings


          The earnings cycle has commenced, and companies are beginning to report their first set of financial results for this year.

          A week ago, Affirm disclosed its financial results. We assess the firm’s performance, tracing its evolution and exploring what likely lies ahead for the BNPL provider.

          AFFIRM

          Affirm’s roots run deep in the desire to rethink how we interact with money, specifically when it comes to buying stuff we want, but perhaps can’t always afford upfront.

          In an increasingly digital world, it’s a business model that resonated with consumers seeking flexibility.

          A look at Q3 2025: Still on the up and up
          Now, let’s talk shop. For Q3 2025, Affirm posted strong numbers that got the analysts sitting up a bit straighter. The company reported a revenue increase of 36% to $783 million in revenue, topping expectations. GMV growth accelerated, up 36% YoY to $8.6 billion. The active consumer base reached approximately 22 million, with nearly 2 million new users in the last quarter. Repeat users still accounted for 94% of all transactions.

          What stands out about Affirm’s performance this quarter is the momentum they’ve built in key growth areas. Consumer spending is bouncing back, and Affirm’s BNPL service is benefiting from that as people are increasingly seeking more control over their finances. But there’s more going on under the hood.


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          Green Dot lends real-world reach to Crypto.com’s digital ambitions

            Crypto meets convenience with Green Dot’s Retail Network


            Green Dot and Crypto.com are teaming up to expand banking and money management features for Crypto.com’s US users — a move that brings traditional financial tools closer to the crypto world. The partnership gives Crypto.com customers new ways to fund and manage their Cash Accounts, including earning interest and depositing US dollars digitally or with cash at Green Dot’s nationwide retail network.

            At the core of the collaboration is Green Dot’s embedded finance platform, Arc, which will power a new interest-earning savings vault and streamline the movement of money into and out of Crypto.com accounts. 

            For Crypto.com, which offers access to more than 350 cryptocurrencies, the added infrastructure could help make digital assets more accessible to mainstream users. And with several locations in the Green Dot Network — ranging from Walmart to CVS — the companies are betting that the real-world utility of crypto begins with meeting customers where they are.

            Why partnerships like these matter: The gap between fiat currencies and digital assets continues to be a major obstacle to broader cryptocurrency adoption. This challenge presents an opportunity for banking-as-a-service (BaaS) providers that already operate within established regulatory frameworks and payment infrastructures to step in and deliver value.


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            While no one was looking, Intuit has built a fintech empire

              Intuit isn’t loud — but it ain’t sleeping either


              If you’ve been keeping tabs on Silicon Valley’s power players lately, you might have noticed something interesting: Intuit has been unusually quiet. No flashy keynotes. No viral product demos. No crypto moonshots or AI-fueled promises to change the world (at least not too loudly IMO). 

              But silence doesn’t mean stasis. The company has been playing its cards close to the chest lately.

              If you zoom out and squint a little, there’s a quiet — but deliberate — transformation underway. Behind the scenes, Intuit is doing what many seasoned companies with established customer bases aim to do: build out an end-to-end ecosystem so sticky and essential that customers don’t want — or need — to leave.

              The firm is likely on that trajectory, making a shift from that tax company into something more expansive: a full-spectrum financial operating system. And it’s doing that through carefully chosen, strategic acquisitions.

              The acquisition spree: In April, Intuit announced plans to acquire Deserve, a mobile-first credit card platform, and also signed an agreement to acquire HR platform GoCo. The press releases were tidy, but the impact of these moves is anything but small.

              They signal a clear thesis: Intuit is doubling down on owning more of the financial lifecycle, especially for small to midsize businesses (SMBs), where it already holds a strong foothold with QuickBooks. But instead of reinventing the wheel, it’s opting to buy the ones that are already spinning efficiently.

              GoCo: The back-office glue


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              The AI Agents are here — and NVIDIA’s sending them to finance

                Inside NVIDIA’s Vision: Deploying Agentic AI in Financial Markets


                The tariff war is throwing punches at the stock market, leaving it dazed and confused, while IPOs — Klarna included — are nervously tiptoeing back into the shadows. It’s a moody scene out there. But instead of wallowing in unstable economic times, let’s take a breather and pivot to something more exciting: AI. Within this broader narrative, we’ll zero in on a California tech firm moving deeper into financial services with its new AI systems.

                Nvidia (NASDAQ: NVDA) has long been recognized for its expertise in designing and producing high-performance graphics processing units (GPUs) — chips that are key components in gaming, professional visualization, data centers, and AI. The firm has seen its technology adopted across a wide range of sectors, from deep learning and autonomous vehicles to scientific research. 

                Now, Nvidia is playing a very different game: it’s quietly becoming one of the influential back-end partners to the financial world’s artificial intelligence (AI) awakening.

                Today, the company is increasingly positioning itself as a foundational infrastructure provider for AI development, with growing influence in financial services beyond its traditional tech roots.

                We explore how.

                AI Agents: Financial firms’ new (non-unionized) analysts


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                Paymentus (US: PAY) CEO Dushyant Sharma on how his firm is modernizing enterprise bill payments with a single code

                  Discover how Paymentus uses AI to navigate industry-specific bill payment demands and compliance


                  For large enterprises, transitioning to cloud-based bill payment systems is no longer just an upgrade — it’s becoming a necessity. Legacy payment infrastructures are often patched together with outdated systems. These systems face challenges with:

                  • Meeting the growing demand for real-time payments.
                  • Adopting AI-driven automation.
                  • Ensuring consistent interoperability across fragmented financial networks.

                  Paymentus, a publicly traded company with the stock ticker PAY, is tackling these challenges head-on. It provides cloud-native bill payment solutions tailored to enterprises across various industries. 

                  Paymentus caters to large enterprises across industries such as utilities, government, finance, healthcare, insurance, and retail. With a focus on high-volume bill payments, the platform is designed to support organizations that handle large transaction volumes and require scalable, automated solutions. The firm also extends its services to mid-sized businesses seeking to upgrade their payment infrastructures.

                  Helping enterprises transition to and scale cloud-based bill payment systems while handling high-volume and sensitive transactions presents its own set of challenges.

                  I spoke with Paymentus CEO Dushyant Sharma about how his company uses AI to meet industry-specific demands and regulatory standards, the hurdles businesses face when adopting cloud-based solutions, and Paymentus’ plans for ongoing tech refinement.

                  Dushyant Sharma, CEO of Paymentus

                  Q: What bill payment challenges does Paymentus solve for large enterprises that traditional systems can’t?


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                  Banks tackle the growing issue of investment banking burnout — But is it actually working?

                    More doing, less debating


                    In the high-stakes world of finance, where metrics move and profits respond, it’s easy to forget that behind every ledger lies a legion of employees. 

                    The financial sector isn’t exactly renowned for its leisurely pace. Historically, junior investment banking jobs have been synonymous with grueling hours, often eclipsing the 100-hour mark in a week, worn like badges of honor. This relentless grind, while lucrative, is a double-edged sword, leading to employee burnout, attrition, and the occasional existential crisis. 

                    In May of last year, advocates loudly criticized the fact that a frazzled employee is about as useful as a screen door on a submarine. The uproar stemmed from the tragic death of Bank of America associate Leo Lukenas, highlighting the need for urgent change. In response, legacy institutions began adopting measures like limiting weekly hours and assigning senior bankers to oversee the well-being of junior staff.

                    While we frequently criticize rigid policies, it’s equally important to acknowledge baby steps some legacy banks are taking to improve employee well-being. Whether these measures are sufficient is another question.

                    We dive into the steps banks have taken to improve work-life balance for employees following the infamous Bofa employee incident, assess whether these initiatives are effective, and where more can be done, all served with a bit of wit and a dash of insight.

                    ​Bank of America implements measures to address junior banker burnout

                    Bank of America had some measures in place to address employee mental health and prevent overwork when the Lukenas incident happened.

                    Post-incident, the bank has implemented additional measures:


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                    BNPL players turn up the heat: Affirm and Klarna compete for banks, growth, and market leadership

                      Where does BNPL belong in the bigger financial picture?


                      The buy now, pay later (BNPL) race has shifted into a new phase. BNPL providers, Affirm and Klarna, initially grew by integrating into e-commerce checkouts, and are now contending for partnerships with major banks. This is also a sign that financial institutions are warming up to the idea of installment-based lending. 

                      Both firms are making big moves to solidify their positions, but their distinct approaches, business models, and competitive strategies bring them advantages, combined with challenges. With Klarna moving toward a public debut and Affirm strengthening its alliances, the two are in the game not just for consumers but also for the financial ecosystem players themselves.

                      A new seeding ground: Big bank partnerships

                      For years, traditional banks dismissed BNPL as an unsustainable lending model, prone to high default rates and regulatory scrutiny. That stance is shifting. With consumer adoption of BNPL surging, major banks are rethinking their position – they are not just tolerating BNPL now but actively making moves to integrate it into their ecosystems. 

                      Affirm’s recent partnership with J.P. Morgan Payments last month is a clear signal that BNPL is no longer just another alternative lending model — it’s mature enough to become embedded within traditional banking. Through this deal, merchants using J.P. Morgan’s Commerce Platform can now offer Affirm’s BNPL loans at checkout, integrating short-term financing directly into the bank’s payment ecosystem. This collaboration puts Affirm in front of a massive merchant base of one of the world’s largest banking networks, solidifying its position as a key BNPL provider in North America.

                      In February, J.P. Morgan also teamed up with Klarna to roll out a B2B BNPL offering, bringing installment payment options to its business customers. Through this partnership, companies using J.P. Morgan Chase’s payments commerce platform will be able to split payments over time, later this year, marking a significant step in BNPL’s expansion beyond consumer retail.

                      How Affirm and Klarna compare — and where they differ


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