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This Month in Fintech

This Month in Fintech

Written by: TWIF
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About this listen

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.


© 2026 This Month in Fintech
Economics
Episodes
  • Leading FIS Through A Fintech Reset with Stephanie Ferris
    Mar 19 2026

    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

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    32 mins
  • AI, Automation, and the Future of Fintech Platforms with Diya Jolly
    Mar 10 2026

    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/


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    30 mins
  • This Month in Fintech with Sasha Pilch
    Mar 6 2026

    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.

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    Less than 1 minute
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