June 11, 2026
This is a special live episode of Barefoot Innovation, recorded at the 2026 American Bankers Association’s Risk and Compliance Conference, where AI was very much at the center of the agenda.
I had the pleasure of sitting down on stage with two longtime friends and colleagues: Raj Date, Managing Partner of Fenway Summer LLC and my very first podcast guest, and Konrad Alt, Co-Founder and Managing Partner of Klaros Group. Between the three of us, we have spent decades working at the intersection of banking, regulation, technology, risk, and innovation.
Our topic was one that is quickly becoming unavoidable for everyone in compliance and risk management: what AI is going to mean for banks, regulators, and the people trying to keep these complex systems safe and sound.
We talked about why compliance and risk management are so hard today, and why AI is arriving at exactly the moment when the industry most needs better tools for seeing into large, complex, fast-changing systems. Raj made the point that AI is already being used, often quietly, to speed up existing workflows, while also raising difficult questions about explainability, auditability, and how deeply these tools can be trusted in a regulated environment. Konrad emphasized that many of the strongest early use cases involve discovery: taking large amounts of unstructured information and turning it into something people can actually use to make decisions.
We also explored where the hype may be outrunning the reality. AI can draft things that look convincing, but that does not mean they are right for a particular institution, risk appetite, culture, or operating model. That will be one of the hardest challenges ahead: combining the power of AI with the judgment, context, and accountability that financial regulation requires.
The conversation ranged from first-line risk management, examiner tools, and the possibility of catching problems earlier, to agentic AI, consumer protection, financial crime, disclosure, liability, vendor risk, and what these changes may mean for community banks and industry consolidation.
My biggest takeaway is that AI is going to bring both tremendous promise and very real danger. It can make compliance faster, smarter, and more proactive. It can also create new risks, new dependencies, and new failures that may be hard to anticipate. As Raj and Konrad both stressed, the most important thing leaders can do now is get their hands dirty: experiment, learn, understand what these tools can and cannot do, and keep returning to first principles about what can go wrong and how to manage it.
One thing is certain: this work is not going to be boring.
Coming up on Barefoot Innovation, we have some wonderful conversations ahead. I’ll be talking with Saket Narayan of AWS, Yaya Fanusie of Aleo, and Greg Ruppert of FINRA, who will give us a glimpse into the regulator of the future.
AIR also has a busy season of events and speaking engagements. We’re now accepting applications for our virtual Global Design Sprint on harnessing gender data for inclusive regulation, beginning July 20, and hosting a closed-door roundtable on the future of financial regulation in a modern economy on June 30 in collaboration with SoFi. I’ll also be speaking at the AWS Summit in Washington, D.C. on July 1. Later in July, AIR’s Shelley Anderson will speak at the Perspectives on Financial Inclusion webinar, and in October, I’ll be joining Nat Weber at Money 20/20 USA in Las Vegas.
As always, you can find more about all of AIR’s work and upcoming events at regulationinnovation.org.
Konrad Alt
Konrad Alt leads enforcement action compliance, risk governance & board advisory services at the Klaros Group.
Konrad has been a trusted advisor to the boards and senior executives of financial institutions and fintech companies ranging from small startups to multinational banking organizations, assisting them with their most complex regulatory, corporate governance and risk management challenges, including helping numerous companies explore and pursue strategies for entering the banking business via both de novo charters and acquisition. Before co-founding Klaros, Konrad served as Chief Banking Officer of the Green Dot Corporation, and Vice-Chairman of the Green Dot Bank board of directors. Immediately before joining Green Dot, he was Chief Operating Officer of Merlon Intelligence, Inc., a regtech startup. Konrad founded and led the Promontory Financial Group’s San Francisco office from 2004-2015, and served as Promontory’s COO from 2014-2016. Before joining Promontory, Konrad served as Executive Vice President and Chief Public Policy Officer at Providian Financial Corp., and as a Senior Vice President at Golden West Financial Corp. From 1989-1996, Konrad was in public service, first as counsel to the U.S. Senate Banking Committee and later as Chief of Staff and Senior Deputy Comptroller at the Office of the Comptroller of the Currency.
Konrad received his BA in Political Science from Reed College, where he is currently a trustee, his JD from Harvard Law School, where he was an editor of the Harvard Law Review, and his MPP in Public Policy from the Kennedy School of Government.
Raj Date
Raj Date is the Managing Partner of Fenway Summer, a Washington, DC-based venture investment firm focused on the financial services sector. He is also the co-founder of FS Vector, an advisory firm that counsels financial services companies on regulatory strategy, compliance and public policy.
Raj has served on the boards of directors of a number of public and private companies across financial services — spanning sectors including banking, payments, insurance, and consumer finance.
For Raj, Fenway Summer is the latest chapter in a long and varied career in and around U.S. financial institutions — as a senior policymaker, as a bank executive, and on Wall Street.
Raj was the first-ever Deputy Director of the U.S. Consumer Financial Protection Bureau (CFPB). As the Bureau’s second-ranking official, he helped steward the CFPB’s strategy, its operations, and its policy agenda. He also served on the senior staff committee of the Financial Stability Oversight Council, and as a statutory deputy to the FDIC Board.
Before being appointed Deputy Director, Raj acted as the interim leader of the new agency, serving as the Special Advisor to the Secretary of the Treasury. He led the CFPB for most of the first six months after its launch.
Before his time in public policy, Raj was a Managing Director in the Financial Institutions Group at Deutsche Bank Securities, where he led the firm’s investment banking coverage for the largest U.S.-based banks and thrifts. His client work focused on calibrating credit deterioration, evaluating capital-raising alternatives, and generating liquidity. Before that, Raj was Senior Vice President for Corporate Strategy and Development at Capital One Financial, where he led M&A development efforts across the U.S. banking and specialty finance markets. He began his business career in the financial institutions practice of the consulting firm McKinsey & Company. He has also served as an attorney in both private practice and government service.
He is a graduate of the College of Engineering at the University of California at Berkeley (highest honors) and the Harvard Law School (magna cum laude).
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