In this episode of the Shift AI Podcast, Jeff Reihl, Technology Chairman at LexisNexis and former CTO, joins host Boaz Ashkenazy to discuss how one of the world's largest legal information companies executed a dramatic pivot to generative AI. Jeff shares the remarkable story of how LexisNexis transformed their entire 2023 strategy in response to ChatGPT's emergence, leveraging their 160 billion document repository to solve AI hallucination problems that plague the legal profession.

From modernizing mainframe systems written in IBM assembly language to implementing multi-model AI strategies using GPT and Claude, Jeff provides a masterclass in enterprise AI adoption. The conversation explores critical topics including maintaining trust and accuracy in legal AI applications, the evolving role of junior lawyers in an AI-augmented world, and how LexisNexis achieved 300% ROI for their customers while dramatically accelerating their own internal processes. Whether you're leading digital transformation at an established enterprise or simply curious about how AI is reshaping professional services, this episode offers invaluable lessons from the frontlines of the legal AI revolution.

Chapters

[01:40] Jeff's Background and Career Journey

[05:54] LexisNexis, RELX, and the Legal Information Industry

[07:21] The ChatGPT Revolution and Strategic Pivot

[10:17] Solving the Hallucination Problem with RAG

[13:26] Liability, Accountability, and the Role of Legal Professionals

[16:16] ROI Metrics and Customer Adoption

[21:02] Agentic Workflows and Strategic Partnerships

[26:18] The Future of Junior Lawyers and Legal Education

[29:05] The Future of Work and Software Development

[31:33] Framework for AI Integration in Organizations

[34:46] Two Words for the Future: Transformative and Personalized

Connect with Jeff Reihl

https://www.linkedin.com/in/jeffreihl/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Alvin Graylin, Digital Fellow at Stanford’s Institute for Human-Centered AI and creator of the Abundantism framework, joins host Boaz Ashkenazy for a bold and wide-ranging conversation on the future of AI and humanity. With a background that spans investing, international leadership, and advanced academic research, Alvin offers a rare, global lens on how we can — and must — steer AI toward positive societal outcomes.

Together, Boaz and Alvin explore three potential AI futures — from Mad Max to Star Trek — and discuss how we can avoid a descent into dystopia by reframing our economic systems, rethinking employment, and redefining human value. The conversation touches on the AI Bill of Rights, the risks of sovereign “gladiator AIs,” and how a new GI Bill for the AI age could help millions transition into a post-labor economy.

If you’re curious about AI’s geopolitical risks, employment disruption, or how we might architect a truly abundant society, this is an essential listen.

Chapters

[01:55] Alvin Graylin's Background: Stanford, XR, Global Ventures

[05:13] Why the Next 5–10 Years Matter for Humanity

[08:04] The Three Futures: Mad Max, Elysium, and Star Trek

[13:33] “Winning the Wrong Race” — The AGI Race and Policy Pitfalls

[17:02] The Real Threat: Bad Actors and Rogue AI Use

[18:40] AI and the Collapse of Traditional Employment

[20:39] What 15–25% Unemployment Could Mean for Society

[23:02] The AI Bill of Rights and the Need for New Protections

[27:10] Surveillance, Data, and Manipulation Risks

[29:52] From Scarcity to Abundantism: The Shift in Mindset

[32:40] Guardian AI vs Gladiator AI: What We Should Be Building

[35:04] The GI Bill for the AI Age and the Need for Soft Landings

[42:03] Start / Stop / Keep: Alvin’s Advice to Tech Leaders

[45:49] Redefining Value: The Two Words That Shape the Future

Connect with Alvin Graylin

LinkedIn: https://www.linkedin.com/in/agraylin/ X (formerly Twitter): https://twitter.com/agraylin

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy Email: [email protected]

The Shift AI Podcast is syndicated by Geekwire and produced by Crumpled Ink Media.

Special thanks to Augmented AI Labs and Clause for sponsoring this episode.

In this episode of the Shift AI Podcast, Court Lorenzini, the founding CEO of DocuSign and now founder of Founder Nexus, joins host Boaz Ashkenazy for a thought-provoking conversation about entrepreneurship, AI, and building a more balanced future for humanity. As a five-time entrepreneur who has experienced both spectacular success and instructive failure, Court brings a unique perspective on how artificial intelligence is fundamentally changing what it takes to build and scale companies today.

From the isolation of the founder's journey to reimagining education systems for an AI-driven world, Court shares his vision for creating abundance rather than scarcity. The conversation explores how AI could be humanity's greatest tool for leveling the playing field, the importance of founder communities, and why we need to rethink our approach to work, purpose, and human dignity. If you're interested in understanding not just the business implications of AI but its profound societal impact, this episode offers invaluable insights from someone dedicated to helping founders succeed while building the future we all want to live in.

Chapters

[02:06] Court's Background and Entrepreneurial Journey

[04:27] The First Paycheck and Worst Job Stories

[07:34] Introducing Founder Nexus and the Founder's Journey

[11:31] How AI is Changing Startup Requirements

[14:04] The Challenge of Differentiation in the AI Era

[17:11] The Lifecycle of Employment and Societal Impact

[20:06] Rethinking Education for an AI Future

[26:16] Dystopian vs Utopian AI Futures

[30:25] What Court is Most Excited and Scared About

[33:30] Creating Abundance Over Scarcity

Connect with Court Lorenzini

LinkedIn: https://linkedin.com/in/court-lorenzini-333447/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

The Shift AI podcast is syndicated by Geekwire and produced by Crumpled Ink Media.

In this special live episode of the Shift AI Podcast recorded at Seattle AI Week, Dr. Andre Alfred, who leads threat operations and security for Google Cloud's Fortune 500 customers, joins host Boaz Ashkenazy for an eye-opening conversation about the intersection of AI and cybersecurity. With his remarkable journey from high school help desk operator to earning his PhD and leading security operations at Microsoft, Oracle, and Google, Andre brings a unique perspective on protecting critical infrastructure in an era where adversaries have access to the same powerful AI tools as defenders.

From data poisoning threats that could compromise healthcare diagnostics to the challenges of securing physical infrastructure like water systems and power grids, Andre shares what keeps him up at night and why two-factor authentication isn't optional anymore. The conversation explores how AI is transforming both offensive and defensive capabilities in cybersecurity, why the next generation of jobs will be defined by leaders rather than technology, and Andre's commitment to visibility as an African American leader in tech. Through his scholarship program at Western Governors University, Andre is opening pathways for the next generation of cybersecurity and healthcare professionals. If you're wondering about the real security threats we're not thinking about—and why the future of work requires "more focus"—this conversation offers crucial insights from someone defending some of the world's most critical systems.

Chapters

[00:00] Introduction and Boaz's Journey to the Shift AI Podcast

[02:37] Andre's Background and Role at Google Cloud Security

[03:44] The Non-Traditional Path: From Help Desk to PhD

[06:25] The Decision to Return to College and Transform Your Career

[08:41] From Capital One to Microsoft to Google

[12:03] What It's Like to Wake Up Every Morning in Threat Operations

[14:21] The Bittersweet Reality: When Innovation Can Be Weaponized

[15:31] Data Poisoning and Healthcare: The Threat We're Not Thinking About

[18:37] Teaching Kids to Question What They See Online

[20:06] Physical Infrastructure Vulnerabilities and Social Engineering

[24:09] The Future of AI and Cybersecurity in 2030

[26:24] Creating Jobs of the Future Through Education

[29:41] The Intersection of Cybersecurity and Healthcare

[32:29] Leaders Must Define the Next Jobs, Not Let Technology Define Them

[33:36] Being Visible as an African American in Tech

[36:11] Two Words for the Future: "More Focus"

Connect with Dr. Andre Alfred

LinkedIn: https://www.linkedin.com/in/aoalfred/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

Special thank you to Western Governers University for hosting and sponsoring this live episode at the Labor Temple in Seattle WA during AI Week.

In this episode of the Shift AI Podcast, Will Jung, Chief Technology Officer at nCino, joins host Boaz Ashkenazy to explore how artificial intelligence is revolutionizing the traditionally conservative banking and financial services sector. Jung brings a distinctive perspective from his extensive experience helping financial institutions transition from viewing technology as a cost center to embracing it as a strategic innovation driver, particularly in the highly regulated world of banking.

From fraud prevention using AI agents that actively lure scammers to context engineering that personalizes banking experiences, Jung offers compelling insights into how banks are deploying cutting-edge technology while maintaining trust and regulatory compliance. The conversation examines the delicate balance between rapid technological advancement and responsible innovation, the future of personalized banking relationships, and why staying human remains the most critical factor in an increasingly automated world. If you're interested in understanding how one of the most regulated industries is navigating the AI revolution while serving underbanked populations and protecting customer data, this episode delivers essential perspectives from a technology leader at the forefront of financial innovation.

Chapters:

[02:00] Will's Background in Banking Technology

[03:00] nCino's Mission in the FinTech Space

[04:30] Banks Embracing Technology as Innovation Driver

[06:50] Fighting Fraud with Advanced AI Technology

[09:00] Building Technical and Non-Technical Team Culture

[11:50] Context Engineering in Banking

[14:25] Privacy and Personalization Trade-offs

[19:20] The Future Customer Experience in Banking

[21:30] Societal Implications of AI Technology

[25:50] Cryptocurrency and Banking Technology

[27:50] Two Words for the Future: Stay Human

[30:00] The Human Element in Automated Banking Decisions

Connect with Will Jung

LinkedIn: https://www.linkedin.com/in/will-jung/?originalSubdomain=au

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Venky Veeraraghavan, Chief Product Officer at DataRobot, joins host Boaz Ashkenazy to explore the fascinating evolution from predictive AI to today's agentic workflows. With 20 years of experience at Microsoft working on everything from Azure Machine Learning to the early days of Azure OpenAI, Venky brings a unique perspective on how AI is truly transforming the enterprise landscape.

The conversation delves into the fundamental differences between predictive and generative AI, how agents will orchestrate complex business processes using multiple AI tools, and what the future holds for the agentic workforce. From warehouse management systems that adapt in real-time to supply chain planning agents that combine forecasting with live data, Venky shares insights on how the orchestration layer of multiple AI tools creates genuinely transformative possibilities.

If you're interested in understanding how enterprises are navigating AI adoption with appropriate caution and what it takes to thrive in an AI-driven workplace, this episode offers invaluable insights from someone at the forefront of enterprise AI transformation.

Chapters

[00:00] Introduction and Background

[02:00] Venky's Journey from Microsoft to DataRobot

[05:00] Predictive vs Generative AI Explained

[09:00] The Evolution of DataRobot's Platform

[13:00] Function Calling and Orchestration Layers

[15:00] The Future of Agentic Workflows

[18:00] Agent Workforce Management and UI Challenges

[23:00] The Human Impact of AI Transformation

[28:00] Enterprise Adoption and Brand Risk

[30:00] Two Words for the Future: Exciting and Disruptive

Connect with Venky Veeraraghavan

https://www.linkedin.com/in/venkyv

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

In this episode of the Shift AI Podcast, Vik Bajaj, CEO and Co-founder of Foresite Labs and Interim President at Xaira Therapeutics, joins host Boaz Ashkenazy to explore how AI is revolutionizing life sciences and healthcare. With a distinguished background spanning physics, structural biology, radiology at Stanford, and pioneering work at Google, Vik brings a unique perspective on the intersection of AI and medicine.

The conversation delves into the stark realities of drug discovery—where 2 million researchers globally struggle against success rates so low that most will be lucky to contribute to one or two successful drugs in their entire careers. Vik explains how AI, particularly David Baker's groundbreaking protein design work, is poised to transform this landscape by enabling drugs for previously "undruggable" targets and moving healthcare from reactive treatment to predictive, personalized medicine.

From genetic tests that could provide actionable insights for 75% of people to AI models that can predict 5-year mortality from a simple chest X-ray, this episode reveals how we're approaching a future where disease prevention replaces disease treatment. If you're interested in understanding how AI will fundamentally reshape healthcare economics and why Vik compares this transformation to the industrial revolution, this episode is essential listening.

Chapters:

[01:48] From Physics to Life Sciences: Vik's Interdisciplinary Journey

[04:13] The Google Years: Early AI Revolution in Science

[06:56] Xaira Therapeutics and David Baker's Protein Design Breakthrough

[09:28] The Optimistic Future of AI in Drug Discovery

[15:17] The Four-Stage Evolution of AI in Medicine

[19:53] Healthcare Cost Crisis and AI Solutions

[23:27] The Promise of Personalized Medicine

[28:39] Foresite Labs: Specializing in Science and Engineering AI

[32:00] Why Healthcare AI is Harder Than Software Engineering

[36:27] Two Words for the Future: Industrial Revolution

Contact Info:

Connect with Vik Bajaj

● LinkedIn: https://www.linkedin.com/in/drvikbajaj/

Connect with Boaz Ashkenazy

● LinkedIn: https://www.linkedin.com/in/boazashkenazy

● X: boazashkenazy

● Email: [email protected]

Shift AI is brought to you by Clause, a legal AI platform, and is syndicated by GeekWire.

In this episode of the Shift AI Podcast, Shalini Agarwal, VP of Product at Salesforce overseeing Slack's AI and search capabilities, joins host Boaz Ashkenazy to explore how AI is transforming workplace collaboration from the inside out. With 17 years of experience at Google and now leading AI innovation at one of the world's most widely used workplace platforms, Shalini offers unique insights into how billions of weekly messages are being augmented with intelligent agents and contextual AI.

From her journey as a seasoned product manager to spearheading Slack's evolution into an agentic work operating system, Shalini reveals how teams are already using AI search, channel experts, and multiplayer agents to unlock institutional knowledge and streamline productivity. The conversation dives into the future of human-agent collaboration, the importance of contextual AI that works in the flow of work, and how Slack is positioning itself as the perfect platform for the next generation of workplace intelligence.

If you're curious about how AI agents will reshape team productivity and what the future holds for contextual, collaborative AI experiences, this episode provides invaluable insights from someone building the future of work today.

Chapters:

[02:00] Shalini's Background and Product Management Evolution

[04:43] Slack's AI Vision and Work Operating System

[09:17] Real-World AI Integration Examples at Slack

[12:26] The Power of Contextual AI in Workflow

[13:56] Customer Adaptation and AI Journey Patterns

[16:02] Agents vs Assistants: Understanding the Difference

[18:14] Surprising Customer Use Cases and Open Text Box Innovation

[21:22] Multiplayer AI Experiences and Team Collaboration

[25:20] Security, Privacy, and Enterprise Data Protection

[25:49] Multiplayer Native Agents Preview

[27:44] The Future of Work: Agentic and Contextual

Connect with Shalini Agarwal

LinkedIn: https://linkedin.com/in/shaliniprofile/

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: [email protected]

Shift AI is brought to you by Clause, a legal AI platform, and is syndicated by GeekWire.

In this episode of the Shift AI Podcast, Sanjna Parulekar, SVP of Product Marketing at Salesforce, joins host Boaz Ashkenazy to explore the reality of enterprise AI adoption beyond the media hype. With her psychology background and eight years at one of the world's leading enterprise software companies, Parulekar offers a grounded perspective on how large organizations are actually implementing AI agents and what the human side of AI transformation really looks like.

From discussing the courage required to transform workflows to the importance of data strategy foundations, Parulekar shares insights on why some companies are succeeding with AI while others struggle with pilots. She also explores how voice technology fits into enterprise solutions, the evolving role of humans in AI systems, and why the future of work will be both more exciting and more intentional. If you're interested in understanding where enterprise AI adoption actually stands versus the narrative, this conversation provides valuable insights from the trenches.

Chapters:

[00:00:35] Introduction and Background

[00:01:56] Sanjna's Journey from AI Startups to Salesforce

[00:03:52] Enterprise AI Adoption Reality vs. Hype

[00:07:16] How Jobs Are Changing with AI Agents

[00:10:30] The Human Experience in AI Transformation

[00:11:25] Voice Technology in Enterprise Solutions

[00:13:56] Humans in the Loop: When and How

[00:18:08] The Truth About AI Hype Cycles

[00:22:13] Big Enterprise Customer Conversations

[00:26:35] Leadership Changes in the AI Era

[00:29:56] Two Words for the Future of Work

Contact Information:

Connect with Sanjna Parulekar

● LinkedIn: https://www.linkedin.com/in/sanjna-parulekar-0248a537/

● Company: Salesforce

Connect with Boaz Ashkenazy

● LinkedIn: https://www.linkedin.com/in/boazashkenazy

● X: boazashkenazy

● Email: [email protected]

In this episode of the Shift AI Podcast, Dr. Vanja Josifovski, CEO of Kumo and former CTO of Airbnb and Pinterest, joins host Boaz Ashkenazy to explore how artificial intelligence is transforming the way businesses unlock value from their structured data. Josifovski shares his journey from building recommendation systems for millions of users to founding Sequoia-backed Kumo, which is tackling one of AI's biggest challenges: turning business data into actionable insights.

From his early days witnessing the evolution of embeddings and vector representations to today's transformer revolution, Josifovski offers a unique perspective on the AI landscape. The conversation delves into why the current AI boom has largely overlooked structured business data, the future of personalized consumer experiences, and how coding tools are democratizing software development. If you're interested in understanding how enterprise data can drive better business decisions and what the future holds for work in an AI-driven world, this episode offers invaluable insights from someone who's been at the forefront of the AI revolution for two decades.

Chapters:

[02:00] Vanja's Background and AI Journey

[04:00] The Evolution of Embeddings and Vectors

[07:00] Silicon Valley's AI Revolution

[09:00] Founding Kumo and the Enterprise Data Problem

[12:00] The Future of Personalization

[15:00] How AI is Changing Software Development

[18:00] The Optimistic Future of Work

[21:00] Societal Changes and Abundance

[25:00] From Big Tech to Startup Life [00:28:00] Two Words for the Future: "Lots of Fun"

Contact Info:

Connect with Vanja Josifovski:

● Website: kumo.ai

Connect with Boaz Ashkenazy:

● LinkedIn: https://www.linkedin.com/in/boazashkenazy

● Email: [email protected]