This Week in Fintech: Spotlight

This Week in Fintech

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This Week in Fintech: Spotlight is our opportunity to take a deep dive into real issues being faced by the fintech industry. Each season focuses on one topic and approaches it from multiple angles, speaking to the leaders at the forefront of innovation in fintech, payments and banking.

1d ago

Why Crypto Could Become the Payment Rail for AI Agents - With Coinbase's Jesse Pollak

In the first episode of the new season of Fintech X AI, host Jillian Williams sits down with Jesse Pollak, creator of Base and a longtime leader at Coinbase, to talk about what happens when AI agents start spending money. Jesse explains why he believes crypto could become a natural payment rail for AI: Agents are built to interact with software, and stablecoins and crypto wallets give them a programmable way to transact without relying on payment systems designed for humans. They discuss where agentic payments are already gaining traction, from micropayments for data and AI inference to the longer-term opportunity in everyday commerce. The conversation also covers Base’s evolution into what Jesse describes as a blockchain for global finance, the growing adoption of stablecoins and tokenized assets, and why major financial institutions have become much more serious about crypto over the past 18 months. Jillian and Jesse also get into one of the harder questions around agentic commerce: what happens when an AI spends the wrong amount, buys the wrong thing, or simply gets it wrong? Jesse shares how payments infrastructure may need to evolve to bring familiar protections like refunds, authorization and consumer safeguards into an agent-driven world. Plus, Jesse explains how AI is changing the way teams inside Coinbase actually work, why smaller teams can now ship dramatically faster, and his prediction that agentic commerce could account for a meaningful share of payments within the next five years. Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Aug 21 · Video

Robinhood Ventures’ Sarah Pinto on Opening Venture Capital to Everyone

What happens when venture capital stops being reserved for a small group of institutions and accredited investors? In this episode of This Month in Fintech, Sasha Pilch sits down with Sarah Pinto, Head of Robinhood Ventures, to discuss Robinhood’s push to open private-market investing to a much broader audience. Sarah explains the thinking behind Robinhood Ventures and its new RV2 fund, which is designed to give retail investors exposure to early-stage companies, including businesses coming out of the Y Combinator ecosystem. They discuss why so much wealth creation now happens before companies reach the public markets, the challenge of giving everyday investors access without sacrificing quality, and why Robinhood believes it can compete for allocations in some of the most sought-after private companies. Sarah also reflects on her path from Goldman Sachs and private equity to Emerson Collective and Robinhood, where her previous investments included companies such as Stripe and OpenAI. The conversation explores women’s participation in investing and wealth creation, the impact AI could have on the next generation of founders, and why Sarah believes expanding access to venture could create not only more investors, but more entrepreneurs. A conversation about venture capital, access, AI, entrepreneurship, and who gets to participate in the upside of the next generation of technology companies. Subscribe for more conversations with the builders shaping the future of fintech. Connect with the Hosts & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch Sarah Pinto: https://www.linkedin.com/in/sarah-pinto-peyronel/ About This Month in Fintech This Month in Fintech is our premiere showcase podcast. Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything again. Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Jul 14 · Video

Scaling Finance From Startup To IPO with Wealthfront's Alan Imberman

Sasha Pilch is joined by Alan Imberman, CFO at Wealthfront, to talk about what it really takes to scale a modern fintech from early scrappiness to a successful IPO, without losing the product instincts that got you there. The conversation starts with the finance leadership side: how the finance function changes across stages, why audits and regulation create discipline, and what the public-company jump demands behind the scenes, from bank selection to testing-the-waters meetings to the S-1 feedback loop. Alan shares what the “ring the bell” moment hides, and why telling the business story clearly becomes a core part of the job. We also cover custodial accounts and tax gain harvesting, plus the early push into a mobile-first mortgage and refinancing product. Finally, we look at AI financial advice, LLM referrals, and how conversational AI could reshape client education and service. Subscribe for more conversations with the builders shaping the future of fintech. Connect with the Hosts & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch Alan Imberman: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/ About This Month in Fintech This Month in Fintech is our premiere showcase podcast. Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything again. Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Jul 3 · Video

How AI Shopping Moves From Chat To Checkout with Adyen's Karan Katyal

AI is changing how people shop, but the real story is what happens after the recommendation. When buying moves into ChatGPT-style interfaces, merchants suddenly face a new maze of platforms, protocols, and trust questions and nobody wants to rebuild checkout for every new “browser” of the AI era. We sit down with Karan, VP, Head of Agentic Commerce at Adyen, to get specific about what’s real today, what’s still early, and what infrastructure has to exist before agents can safely transact at scale. We break agentic commerce into four clear models: human-in-the-loop conversational checkout, consumer autonomous purchasing, machine-to-machine transactions, and B2B agentic procurement. Then we dig into the “universal translator” approach: real-time product feeds for discovery, cart creation that plugs into a merchant’s existing tax and fulfillment stack, and a payments trust layer that keeps transactions secure while preserving the merchant as merchant of record. Subscribe for more conversations with the builders shaping the future of fintech. Connect with the Hosts & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch Karan Katyal: https://www.linkedin.com/in/karan-katyal-14070438/ About This Month in Fintech This Month in Fintech is our premiere showcase podcast. Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything aga Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Jun 25 · Video

Why Finance Teams Are Moving From Cloud to AI

In this episode, host Sasha Pilch sits down with John Glasgow, CEO and CFO of Campfire, to explore what it takes to build an AI-native ERP for modern finance teams. John shares why the next major shift in accounting software is not from on-premise systems to the cloud, but from cloud tools to AI-native platforms. They discuss the reporting, consolidation, and planning challenges that still force finance teams into spreadsheets, along with Campfire’s approach to automating routine workflows while keeping governance and business context at the center. The conversation also covers John’s path from investment banking and corporate finance at Adobe to building Campfire through Y Combinator, plus his view on how AI agents and connected data can change the role of the general ledger. Subscribe for more conversations with the builders shaping the future of fintech. This episode is sponsored by Granola. Try it free for 3 months at granola.ai/thisweekinfintech using code THISWEEKINFINTECH. Connect with the Hosts & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch John Gasglow: https://www.linkedin.com/in/johnglasgow/ About This Month in Fintech This Month in Fintech is our premiere showcase podcast. Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything aga Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
May 28

How Experian Is Making Agentic Commerce Trustworthy

AI agents can already shop, compare prices, and check out for you — but would you actually trust one with your credit card? In this episode of This Month in Fintech host Sasha Pilch sits down with Kathleen Peters, Chief Innovation Officer at Experian, to explore the trust layer behind agentic commerce. From the shift from KYC to KYA (“Know Your Agent”) to Experian Agent Trust and digital identity tokens, they unpack how AI-driven payments could become safer for consumers, merchants, and the broader financial ecosystem. They also dive into fraud prevention, open standards, Cloudflare, Visa, stablecoins, and what trustworthy agentic transactions could look like in the real world. Subscribe for more conversations with the builders shaping the future of fintech. This episode is sponsored by Granola. Try it free for 3 months at granola.ai/thisweekinfintech using code THISWEEKINFINTECH. Connect with the Hosts & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch Kathleen Peters: https://www.linkedin.com/in/kathleenhpeters/ About This Month in Fintech This Month in Fintech is our premiere showcase podcast. Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything aga Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Apr 21

From Screen Scraping to Open Banking with Ximena Aleman

In this episode of This Month in Fintech, Sasha Pilch sits down with Ximena Aleman, Co-founder and Co-CEO of Prometeo, to unpack what it really takes to build a single banking API across Latin America and the US. They dig into the realities of cross-border fintech infrastructure, from early workarounds like screen scraping to the impact of Brazil’s open banking movement, and how Prometeo is pushing banks toward API adoption. Ximena also shares lessons from scaling across fragmented markets, raising a Series A during a downturn, and navigating the challenges founders face in LATAM. They also explore where LATAM fintech could gain ground in the US, from cross-border payments and remittances to new approaches to credit for underserved populations. Subscribe for more conversations with the builders shaping the future of fintech. This episode is sponsored by Granola. Try it free for 3 months at granola.ai/thisweekinfintech using code THISWEEKINFINTECH. Connect with the Hosts & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch Ximena Aleman: https://www.linkedin.com/in/ximena-aleman/?locale=en_US About This Month in Fintech This Month in Fintech is our premiere showcase podcast. Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything again. Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Mar 19

Leading FIS Through A Fintech Reset with Stephanie Ferris

We talk with FIS CEO Stephanie Ferris about building a career by leaning into risk, leading teams through complex M&A, and simplifying a legacy fintech business to focus on financial institutions. We also dig into why trust is the real infrastructure of banking, how tokenization is evolving, and why AI should make fintech leaders more optimistic, not fearful. • Career path from PwC to Fifth Third to Vantiv to FIS, prioritizing tough roles and high learning curves • How major M&A really happens, from long strategy conversations to relationship-driven execution • Why FIS separates Worldpay and what the three-party transaction changes operationally • Build versus buy in payments, and the scarcity of scaled credit card processing assets • Trust as the foundation of financial services, lessons from SVB, 9/11, and COVID-era stress • How banks and fintechs compete and partner, including shifting regulatory dynamics • Stablecoins and tokenized deposits, practical use cases and what remains nascent in the US • Imposter syndrome, coaching, and doing the reps as a leadership skill • Generative AI as a strategic accelerant, and what it means for product delivery and speed Connect with the Host & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch Stephanie Ferris: https://www.linkedin.com/in/stephanieferris Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Mar 10

AI, Automation, and the Future of Fintech Platforms with Diya Jolly

We sit down with Xero’s CTO/CPO Diya Jolly to unpack how AI, product conviction, and human judgment are reshaping small business finance. From JAX, Xero’s financial superagent, to passwordless lessons at Okta, we dig into saving time, making better calls, and building faster. • Xero vs QuickBooks and why orchestration matters • Jax as a unified financial superagent • Transparent automation that invites human override • Data moats and domain depth as AI advantages • Focus markets across ANZ, US and UK • Auto bank reconciliation and 22 hours saved per month • One leader across product and technology • Reversible vs one-way-door decisions and speed • Career jumps for learning over brand • Betting on passwordless and proving security with less friction • Google lessons on pairing data with intuition • The next decade of fintech UX beyond dashboards Connect with the Host & Guest Sasha Pilch: https://www.linkedin.com/in/sasha-pilch Diya Jolly: https://www.linkedin.com/in/diyajolly/ Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Mar 6

This Month in Fintech with Sasha Pilch

Announcing the next chapter of the This Month in Fintech Podcast. We are excited to welcome Sasha Pilch as the new host, leading conversations with the founders, operators, and thinkers shaping the future of fintech. Each episode will explore the ideas, products, and decisions driving the next generation of fintech, from AI and financial infrastructure to the platforms redefining how businesses and consumers interact with money. Join Sasha as she sits down with leaders across the ecosystem to unpack what is working, what is changing, and what comes next for the global fintech community. Tune in for thoughtful conversations, practical insights, and a front row seat to the people building the future of finance. Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Feb 26

Anthropic's Kate Earle Jensen: Enabling AI in the Enterprise

In today’s episode, Ryan Zauk sits down with Kate Earle Jensen, Head of Americas for Anthropic. Kate joined Anthropic in 2023 after 8 years helping scale GTM at Stripe. Over the last 2 years, she has had a front row seat to the AI revolution at one of the fastest-growing companies in history. In this episode, Kate dives into how Claude is being used by major enterprises to revolutionize their businesses, the state of Anthropic’s products and MCP, why they built in the application layer for financial services, what key blockers remain for enterprise adoption, why AI’s market size allows them to approach partnerships in a unique way, transitioning from Stripe to Anthropic, why siblings make great leadership teams, and much more. #Anthropic, #FinTech, Software, #ai , #MCP, Claude, #Go-to-Market, #Leadership, #Innovation, #financialservices , #Partnerships, #Coding, #vibecoding , #Stripe, #hackathon n Takeaways The AI market is unquantifiably large, which helps you play non-zero sum games in GTM, partnerships, and product. It helps breed greater collaboration because you know there is more than enough revenue opportunity to share. Hackathons, though not new, have proven to be one of the best sources of discovering novel AI applications in the enterprise. We host them internally and encourage our clients to do host them to get employees experimenting and uncover the art of the possible. Financial Services + Healthcare are proving to be the best industries for AI. They have huge data sets, antiquated technology systems, and manual workflows that make them prime candidates. AI is only as good as the quality of data and context that you feed it. It is as important as anything you choose, which is why MCP became so popular. Siblings often make the best cofounding teams. The Collisons and Amodeis both have very strong working styles that allow them to be brutally honest with each other while not breaking relationships. Follow This Week in Fintech Linkedin X Instagram TikTok YouTube
Feb 26

Sierra CEO & OpenAI Chair Bret Taylor - Live at M2020. AI Bubbles, SaaS Future, and Why Sierra WinsUntitled Episode

In today’s episode, Ryan Zauk sits down with Bret Taylor, Co-Founder & CEO of Sierra and Chairman of the Board at OpenAI. Bret’s career is the stuff of valley legend…he is the former Co-CEO of Salesforce, former CTO of Facebook, and has been credited with building products like Google Maps and Facebook's 'Like' button. There may not be anyone closer to AI, spanning the app layer all the way down to its core foundation. In this episode, Bret and Ryan explore several topics including how Sierra has transformed customer service, the agentic era and its consequences for software, why we ‘might’ be in an AI bubble, how Sierra differentiates to win customers like Ramp, Rocket, and Brex, where AI moats will accrue, the 3 AI megatrends he’s leaning into, and much more. Key Takeaways “Every company’s AI agent will be as important as their mobile app or their website.” Bret sees a future where AI agents replace apps and websites as the first point of contact for customers. Agents will handle workflows end to end (fraud reports, mortgage refis, account changes) across all channels, languages, and modalities. CS agents are showing immediate ROI on both the top and bottom line…For example, Rocket’s customers who engage with a Sierra agent are 3x as likely to complete a transaction vs. traditional service. At Ramp, their self-service resolution rate with Sierra’s agents is over 90%. Healthcare giant Cigna is replatforming its IVR with Sierra…using AI will help businesses rethink their operating model. Outcome pricing raises the stakes for software, morphing them into true business partners. Outcome pricing will create accountability, transparency, and measurable ROI in an era of vague productivity claims. The Future of AI is 3 things. 1) Multimodal - seamless voice experience. 2) Personalized - knowing your context, preferences, and intent. 3) Proactive - solving a problem before it arises or before the customer knows it has occurred. It’s an AI bubble, but a healthy one. The fundraising hype is alarming, but the underlying transformation is real. Similar to 1999, many firms will fail, but some will become generational winners. If you bought pets.com you lost your money. If you bought Amazon, you made history. Follow This Week in Fintech Linkedin X Instagram TikTok YouTube

12 Episodes

This Week in Fintech: Spotlight is our opportunity to take a deep dive into real issues being faced by the fintech industry. Each season focuses on one topic and approaches it from multiple angles, speaking to the leaders at the forefront of innovation in fintech, payments and banking.

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This Week in Fintech
Years Active

2026
Episodes

12
Rating

Clean
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© 2026 This Week in Fintech: Spotlight
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This Week in Fintech: Spotlight