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

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/

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.

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.

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.