In this episode of the Shift AI Podcast, Arnab Bose, Chief Product Officer at Asana, joins host Boaz Ashkenazy to explore how artificial intelligence is transforming the way teams collaborate and get work done. Bose shares his journey to becoming CPO at Asana and the company's ambitious vision for human-AI collaboration, including their groundbreaking AI Teammates and AI Studio products.

From the early days of smartphones reshaping work behavior to today's AI agents that can automate the "toil aspects" of project management, Bose offers a compelling look at where workplace productivity is heading. The conversation dives into how Asana is building a structured approach to work that enables AI agents to seamlessly collaborate alongside human teammates, what customers are actually asking for when it comes to AI tools, and how to build defensible enterprise products through security, governance, and simplicity.

If you're interested in understanding how AI is moving beyond individual productivity gains to transform entire team workflows, what it takes to build competitive moats in enterprise software, and what the future holds for managing AI agents in the workplace, this episode offers invaluable insights from a product leader at the forefront of the AI-powered future of work.
Chapters

[00:00] Journey to Asana: Embracing AI Collaboration

[06:22] Transformations in Work: AI's Impact on Productivity

[11:50] Asana's Vision: Human and AI Collaboration

[17:26] Industry Insights: Customer Needs and AI Adoption

[22:25] Building a Moat: Strategies for Competitive Advantage[

25:26] Future Predictions: The Evolution of Work and AI
Connect with Arnab BoseLinkedIn: https://www.linkedin.com/in/abosesf/
Connect with Boaz AshkenazyLinkedIn: https://linkedin.com/in/boazashkenazyEmail: [email protected]

In this episode of the Shift AI Podcast, Eilon Reshef, Co-founder and Chief Product Officer at Gong, joins host Boaz Ashkenazy to explore how artificial intelligence is revolutionizing revenue operations and transforming the future of sales teams. Reshef shares the decade-long journey of building Gong from a data-driven conversation platform into what they call an "AI OS for Revenue Teams," serving Fortune 10 companies and pioneering the use of AI in go-to-market workflows.

From capturing customer conversations to deploying AI agents that can automate mundane tasks, Reshef offers a compelling vision of where sales productivity is heading. The conversation delves into how AI is making revenue teams more efficient and effective, the transformation of traditional sales roles, and why the biggest shift isn't just in technology but in how quickly organizations can execute and adapt. If you're interested in understanding how enterprise AI is moving beyond hype to deliver measurable productivity gains, how unstructured data creates competitive advantages, and what the future holds for revenue professionals in an AI-driven world, this episode offers invaluable insights from someone building the infrastructure that's reshaping B2B sales.

Chapters

[00:00] Introduction and Welcome

[02:15] Eilon's Background and Journey to Gong

[05:30] The Origin Story: Starting Gong 10 Years Ago

[08:45] First and Worst Jobs

[11:00] The ChatGPT Moment and AI Acceleration

[14:30] Gong's Unfair Advantage with Unstructured Data

[17:00] Three Pillars of AI Transformation

[21:15] The Rev Ops Revolution

[24:00] Enabling Sales Teams with AI

[27:30] What's Hype vs. Reality in AI for Revenue

[31:00] The Future of Sales Roles and Team Structure

[33:45] The Platform Strategy and Integrations

[36:30] Security and Trust in Enterprise AI

[39:00] Gong's Growth Trajectory and Future Plans

[41:30] Voice Agents and the Future of Customer Interaction

[45:00] Two Words for the Future: Efficient and Exciting

[48:00] Connecting with Eilon and Hiring at Gong

Connect with Eilon Reshef

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

Connect with Boaz Ashkenazy

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

Email: [email protected]

In this episode of the Shift AI Podcast, Rob Lloyd, Chief Technology Officer of the City of Seattle, joins host Boaz Ashkenazy to discuss Seattle's groundbreaking approach to implementing artificial intelligence in municipal government. Lloyd shares his journey from serving multiple cities across America to spearheading one of the nation's most progressive urban AI initiatives, revealing how Seattle is transforming public services through thoughtful technology adoption.

From traffic safety innovations to permitting process overhauls, Lloyd offers a candid look at the successes and failures of Seattle's AI pilots, including the surprising revelation that 80% of initial experiments didn't stick.

The conversation takes an unexpected turn when Joe Nguyen, Director of Commerce for Washington State, joins to discuss statewide AI efforts, creating a rare dialogue between city and state technology leaders. If you're interested in understanding how government can responsibly deploy AI to serve communities better, this episode provides practical insights from leaders navigating the complex intersection of public service, technology, and trust.

Chapters

[00:00] Introduction and Rob's Journey to Seattle

[03:30] Career Path Through Multiple Cities

[06:45] Growing Up in a Military Family

[09:15] First Jobs and Character Building

[12:00] Seattle's AI Plan Genesis and Evolution

[16:30] Policy Framework and Community Trust

[20:15] Pilot Programs: Success and Failure Rates

[24:45] Traffic Safety and Game Theory Applications

[28:00] Permitting Process Transformation

[32:30] Special Guest: Joe Nguyen from Washington State

[35:15] State-Level AI Implementation at Commerce

[38:45] Cultural Shifts and Future Vision

Connect with Rob Lloyd

LinkedIn: https://linkedin.com/in/rob-lloyd-cto-seattle/

Connect with Joe Nguyen

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

Connect with Boaz Ashkenazy

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

Email: [email protected]

In this episode of the Shift AI Podcast, Yash Wagh, Co-Founder and CEO of Gone, joins host Boaz Ashkenazy to explore how reverse logistics and AI are transforming the secondhand goods market into a sustainable circular economy. With a background as a rocket engineer, supply chain leadership at Amazon and A.T. Kearney, and a passion for sustainability, Yosh is building autonomous local commerce infrastructure that keeps valuable goods out of landfills and in circulation.

From his journey as a mechanical engineer designing rocket propulsion systems to pioneering AI-powered reverse logistics, Yosh shares how Gone is solving the complex challenges of secondhand commerce. The conversation explores the business economics of circular economies, the role of AI in automating pickups and pricing, and a bold vision for a future where autonomous systems connect millions of households through local meshes of commerce. If you're interested in climate-conscious innovation, AI-powered logistics, sustainable consumerism, and the future of work in an AI-driven world, this episode offers invaluable insights from an entrepreneur building the infrastructure of tomorrow's circular economy.

Chapters

[00:00] Introduction and Welcome

[03:15] From Rocket Science to Reverse Logistics

[06:30] First Jobs and Career Journey

[10:45] What is Gone - Reverse Amazon Explained

[16:20] The Problem with Current Donation Models

[19:40] Business Economics and Unit Economics

[24:15] AI Technology and Automation in Action

[29:50] The Entrepreneurial Journey and Challenges

[35:10] Negotiating the Gone.com Domain Name

[37:45] The Future of Autonomous Local Commerce

[43:20] How to Connect with Gone

Connect with Yash Wagh

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

Website: https://gone.com

Shop: https://shop.gone.com

Connect with Boaz Ashkenazy

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

Email: [email protected]

In this episode of the Shift AI Podcast, Christian Lund, Co-Founder of Templafy, joins host Boaz Ashkenazy to explore how cognitive collaboration between humans and AI is transforming enterprise document creation. Broadcasting from Copenhagen, Christian shares his unique journey from newspaper sales to building one of the leading document automation platforms serving over 800 enterprise clients worldwide, including KPMG and IKEA.

From navigating technology shifts spanning on-premise to cloud to AI, Christian offers invaluable insights on what separates successful AI implementations from the 40% of projects that fail. The conversation dives deep into why purpose trumps capability when deploying AI, how Templafy helps companies save millions annually while reducing risk, and the evolution from traditional templates to AI-powered document generation. Whether you're an executive trying to drive meaningful AI adoption or an entrepreneur building in the AI space, Christian's perspective on connecting human intent with AI intelligence offers a roadmap for the future of work.

Chapters:

[00:00] Introduction and Welcome

[02:00] Christian's Background and Journey to Templafy

[06:00] What Templafy Does: Enterprise Document Automation

[09:00] How AI Transformed Document Generation

[12:00] Why 40% of AI Pilots Fail and How to Succeed

[17:00] ROI and Multimodal Content Creation

[21:00] Advice for Deploying AI Agents

[26:00] Cognitive Collaboration: Humans and AI Working Together

[28:00] Job Displacement Concerns in Europe

[30:00] Two Words for the Future

Connect with Christian Lund

LinkedIn: https://dk.linkedin.com/in/christianlundcph

Website: https://templafy.com

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 episode of the Shift AI Podcast, Michael Domanic, Head of AI at UserTesting, joins host Boaz Ashkenazy to explore how companies can successfully transform their organizations with AI. With over 800 custom GPTs built across UserTesting and nearly every employee actively using AI tools, Michael shares the framework behind one of the most successful enterprise AI transformations happening today.

From his early days designing chatbots during the first AI hype cycle to leading transformation at scale today, Michael offers invaluable insights into why AI transformation is fundamentally a change management and creative challenge—not just a technological one. The conversation delves into the responsibility companies have to their workforce during this historic transformation, the importance of democratizing AI access, and why focusing on human creativity and experimentation is the key to unlocking real value. If you're looking to understand how to drive meaningful AI adoption in your organization while keeping humanity at the center, this episode is essential listening.

Chapters:

[00:00] The Human Side of AI and Creativity

[02:00] Michael's Background and the First Chatbot Wave

[04:00] First Jobs: From Lifeguard to Telemarketer

[05:00] What is UserTesting and How It Works

[08:00] The Challenge of Enterprise AI Adoption

[11:00] Why Multiple AI Models and 800+ Custom GPTs

[15:00] Change Management Over Technology

[19:00] AI's Impact on Jobs and Employee Responsibility

[22:00] Growth Mindset vs. Scarcity in AI Strategy

[24:00] Healthcare and the Future of AI

[27:00] Two Words for the Future: Human and Creativity

[29:00] Measuring ROI in AI Transformation

Connect with Michael Domanic

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

Connect with Boaz Ashkenazy

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

Email: [email protected]

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.