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Why do so many financial institutions struggle to scale AI beyond pilots?

Amman, Chief Strategy Officer at Tribeca Softech, joins Ankur on Pioneers to unpack the realities of AI adoption in financial services. Despite widespread experimentation with AI, Amman explains why only a small fraction of organizations achieve enterprise-wide impact—pointing to misalignment, legacy system constraints, and cultural resistance as key blockers. The conversation explores how governance, compliance, and risk management can become competitive advantages, the differences in AI maturity between mid-market firms and large enterprises, and what lagging organizations can learn from early adopters. They also discuss generative AI’s growing influence and the strategic role AI plays in private equity decision-making.

Timestamps:

00:00 Introduction: AI Adoption and Scaling Challenges

02:33 Guest Introduction: Amman from Tribeca Soft Tech

03:44 AI as a Business Transformation Tool

04:35 Challenges in AI Implementation

05:50 Strategies for Financial Institutions

10:01 Mid-Market vs. Enterprise AI Adoption

23:18 Private Equity and AI Adoption

27:00 2026 AI Adoption Insights

35:09 Conclusion and Future Outlook

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How is AI bridging the gap between credit unions and FinTechs?

Julie Esser, founder of IgniteFI, joins Pioneers to discuss the rapid advancements in AI and its critical role in transforming credit unions. Julie explains how aligning values, scalability, and compliance can drive successful partnerships between credit unions and FinTechs. She also highlights the role of Credit Union Service Organizations (CUSOs) in providing smaller credit unions with access to modern digital solutions. The conversation delves into common obstacles in FinTech adoption, the importance of data readiness, and actionable advice for credit unions to stay relevant through innovative collaborations without losing sight of their member-first mission.

Timestamps:

00:00 Introduction to AI in Credit Unions

02:20 Meet Julie Esser: A FinTech Matchmaker

03:00 The Role of FinTech in Credit Unions

04:08 Challenges and Benefits of FinTech Partnerships

05:22 The Importance of CUSOs

07:51 Evaluating FinTech Partnerships

08:51 Future of Credit Unions with Emerging Technologies

12:43 Ignite FI: Bridging the Gap

18:33 AI Adoption in Credit Unions

34:39 Conclusion and Final Thoughts

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How can AI modernize insurance without losing the human element

Justin Hinson, Product Leader at CompSource Mutual, joins Pioneers to explore where AI truly fits, and where it doesn’t, in workers’ compensation insurance. Drawing on more than 25 years across claims, underwriting, and product, Justin explains why one of the most regulated and personal lines of insurance resists full automation, and why human judgment and empathy remain essential. He breaks down how AI creates real value today by preparing work for adjusters and underwriters, not replacing them, and why data readiness, workflow quality, and governance must come before any AI rollout. The conversation also covers how to cut through vendor noise, build trust and adoption internally, and introduce AI in a way that improves speed and insight without sacrificing care for injured workers.

Timestamps:

00:00 Introduction to AI in Insurance

02:16 Guest Introduction: Justin Hinson's Journey

03:16 Justin's Career Path and Technological Evolution

07:08 Challenges in Workers' Compensation

11:42 AI's Role in Enhancing Insurance Processes

22:24 Selecting the Right AI Vendor

27:51 CompSource's Approach to AI Adoption

33:14 Future Directions and Advice for Carriers

45:19 Concluding Thoughts and Final Remarks

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How is AI reshaping one of the most regulated industries in finance?

Jason Harris, Strategic Initiatives Manager at American Portfolio Mortgage, joins Pioneers to unpack how AI is transforming mortgage lending from the inside out. Drawing on deep industry experience, Jason explains why a highly commoditized, Dodd-Frank–regulated market is primed for disruption, and how automation is already changing everything from underwriting to borrower experience. He shares why reducing manual processes is no longer optional, what lenders risk by delaying AI adoption, and how today’s shift mirrors past industry shakeups. The conversation also explores the broader macroeconomic backdrop, the future of interest rates, and how lenders should think about building, buying, or partnering on AI to stay competitive and scale responsibly.

Timestamps:

00:00 Introduction to AI in the Mortgage Industry

02:12 Guest Introduction: Jason Harris

02:39 Evolution of Mortgage Technology

04:33 Automation and AI in Mortgage Processes

07:32 Current Applications of AI in Lending

10:34 Impact of AI on Mortgage Professionals

16:33 Macro Environment and Market Trends

22:22 Strategic Investments in AI

25:50 Build vs. Buy: AI Solutions for Lenders

29:53 Conclusion and Final Thoughts

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How do enterprises move from AI experimentation to real, scalable impact?

Tim Piemonte, President and Co-Founder at Tribeca Softech, joins Ankur Patel to break down what it actually takes to implement AI successfully inside large organizations. Drawing from hands-on enterprise experience, Tim explains why aligning key stakeholders early is non-negotiable, how security and governance shape every AI decision, and why education and skill development often matter more than tooling. He also shares how leaders can communicate AI value to the C-suite, evaluate internal capabilities, balance quick wins with long-term strategy, and cut through the noise in an increasingly crowded AI vendor landscape.

Timestamps:

00:00 Introduction to AI and DevSecOps

02:03 Guest Introduction: Tim Piemonte

02:43 The Importance of AI Strategy

03:48 Challenges in AI Adoption

05:21 Interdependencies in AI Implementation

08:08 Shadow IT and AI

09:40 People, Process, and Platform

15:40 Quick Wins and ROI in AI

27:14 Build, Buy, or Partner: Navigating AI Solutions

34:11 The Role of the CISO in AI Implementation

37:27 Conclusion and Final Thoughts

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How are traditional banks reinventing themselves for the fintech and AI era?

Izge Cengiz Ercan, Director of Strategic Innovation at Valley Bank, joins Ankur Patel to share how she’s bridging legacy banking with emerging technologies, from agentic AI to startup partnerships and responsible innovation frameworks. She reveals why speed and governance don’t have to conflict, and how collaboration with risk and compliance teams can actually accelerate adoption.

Timestamps:

00:00 Introduction: AI in Banking

00:09 Future of Commercial Lending

00:18 Build vs Partner: The Next Five Years

00:28 Defining Innovation in 2026

00:37 Common Mistakes with Fintechs

00:49 Overhyped AI Trends

01:03 Key KPIs for Innovation

01:11 Challenges in Scaling Innovation

01:22 Misconceptions About Bank Innovation

01:34 Future of Strategic Innovation

01:45 Conclusion

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How is AI reshaping one of the world’s largest energy companies?Mubina Dunn, Enterprise AI and Innovation Strategy Leader at NextEra Energy, joins Ankur Patel to discuss how her team is driving adoption across 80-90% of employees, blending predictive analytics, generative AI, and agentic systems to transform operations. From predictive maintenance to internal GPTs, she shares how innovation can thrive, even in a regulated industry.

Can AI make brokers superhuman instead of obsolete?

Cheynna Massie, Managing Partner & CFO at Massie Risk and Founder of Agent 3, joins Ankur Patel to discuss how generative AI is reshaping commercial insurance, from automating back-office tasks to scaling broker intelligence. She breaks down why the real profit bottleneck isn’t technology, but human bandwidth, and how Decision AI can change that equation.

Can AI finally fix the broken economics of fleet insurance?

Felix Kuhlmann, co-founder of Drive-In and Insurance Executive in Residence at Accenture’s FinTech Innovation Lab, unpack why commercial fleet insurance has been unprofitable for decades and how agentic AI, telematics, and better data pipelines could change that. From underwriting to risk sharing, Felix explains where AI can truly deliver impact for carriers and fleet operators alike.onomics of fleet insurance?

Why is AI adoption in financial services so slow?

According to NayaOne’s Managing Director, Scott Sambucci, it’s the bureaucracy, not technology gaps.In this episode, he joins Ankur Patel to unpack what’s really stopping organizations from adopting AI, like endless committees, and share frameworks for testing AI responsibly, yet quickly. Tune in to learn why you should run structured validations and build a “fail fast” internal culture.