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Shift AI with Boaz Ashkenazy

Boaz Ashkenazy

Weekly conversations with the executives putting AI to work inside the world's organizations: the tradeoffs, the failures, and the decisions that never make it into a keynote. Hosted by Boaz Ashkenazy, syndicated by GeekWire. shiftai.fm

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  • 27 episodes
  • Avg 35 min
  • English

Episodes 27

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  • April 17 · 33 min

    How AI is Rewriting Software Engineering with Amperity CTO Derek Slager

    In this episode of the Shift AI Podcast, Derek Slager, CTO and co-founder of Amperity, joins host Boaz Ashkenazy for a conversation that spans 10 years of company building, the evolution of AI-assisted software development, and what it really means to lead a technical organization through genuine disruption. Derek shares the founding story of Amperity, how he and co-founder Kabir Shahani stumbled into the customer data problem while building marketing automation at their previous company, Aperture, and how that experience became the thesis for building an entire platform around getting data right. The conversation moves into the heart of how AI has transformed Derek's work as a CTO and as an engineer. He describes the moment the shift felt real, the team dynamics of moving from individual AI exploration to a true team sport, and how Amperity is compounding the institutional knowledge locked in a decade of after-action reviews into something agents can now actually learn from. Derek addresses the "SaaS is dead" narrative head-on arguing that Amperity's data foundation is precisely the asset that makes agents genuinely useful for their customers. Boaz and Derek close with a forward-looking exchange on agentic workflows in marketing, the importance of redesigning process and what a learning mindset means for individuals and organizations navigating what comes next. This episode is essential listening for CTOs, data leaders, and operators who want to understand how the companies with the best data foundations are positioned to thrive in the agentic era. Chapters [00:00] Introduction: Derek's Path to Building Amperity [02:13] What Amperity Is and Why It Took 10 Years to Build [04:41] First Job: Early IT Work at Dad's Small Business in Monroe, WA [06:14] The Founders Club: How Amperity Went to Market in 2016 [08:20] Why They're Running a New Founders Club 10 Years Later [10:13] Both Sides of Claude Code: What Changed and When [13:30] Living Through Disruption as a CTO and Engineer [15:36] Making AI a Team Sport Instead of an Individual Pursuit [17:04] The Moment It Really Clicked: A Simple Tool That Took 5 Minutes to Build [19:09] Cultural Adoption: Skeptics to Believers Inside Amperity [21:50] Compounding Engineering: After-Action Reviews as AI Training Data [23:45] The Agent Wave Is Real: What It Means for a Customer Data Platform [25:09] Amperity's Data Foundation as the Perfect Agent Substrate [27:00] Redesigning Process, Not Just Adopting Tools [28:57] Systems Thinking and the Future of Work [30:04] Two Words: Learning Mindset [33:01] How to Connect with Derek and Amperity Connect with Derek Slager LinkedIn: https://www.linkedin.com/in/derekslager/ Website: amperity.com Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  • April 9 · 36 min

    Proving Your Humanity in the Age of AI Agents with Tools for Humanity World ID Head Ajay Patel

    In this episode of the Shift AI Podcast, Ajay Patel, Head of World ID at Tools for Humanity, joins host Boaz Ashkenazy for a timely and wide-ranging conversation on the identity crisis facing the internet in the age of AI agents. Ajay shares his career journey from hardware engineering to product and sales, through years at Google leading payments identity infrastructure managing how legal identity, verification, and payment data move across the entire company globally and ultimately to Tools for Humanity, where he saw the chance to tackle the root-level problem that his work at Google kept circling: if you don't know who you're dealing with, everything downstream breaks. The conversation digs into why the entire internet was built with the assumption that users are human and why that assumption is now collapsing as AI agents multiply. Ajay walks through the founding principles of World ID: privacy-preserving proof of humanity, uniqueness without revealing identity, and an open-source, decentralized architecture designed to have no single point of failure. He covers the challenge of making this system easy enough for non-technical users while still being cryptographically robust, and why inclusivity ensuring the billion people without legal identity can still participate is a core design constraint, not an afterthought. Boaz and Ajay explore the partnership with Coinbase and Cloudflare, how agent delegation will work in practice, what agentic commerce means for coupon fraud and chargebacks, and what a world with a hundred agents acting on your behalf could actually look like. The episode closes with a forward-looking discussion on new builders, mobile-first parallels, and why the certainty World ID brings to online interaction will unlock things we can't yet imagine. This episode is essential listening for anyone thinking about identity, trust, agentic systems, and what the infrastructure of the next internet needs to look like. Chapters [00:00] Introduction: Ajay's Journey from Hardware Engineer to World ID [02:02] The Identity Problem at the Heart of Google Payments [05:15] What Led Ajay to Tools for Humanity [07:33] The World ID Origin Story and Sam Altman's Vision [08:17] Why Every Internet System Assumes You're Human and Why That's Breaking [10:46] What World ID Is and How the Real Human Network Works [12:18] Open Source, Decentralized, and the Principles Behind the Architecture [13:37] Privacy, Security, Performance, and Inclusivity as Design Constraints [14:08] The Billion People Without Legal Identity [15:03] The Aadhaar and UPI Example: What Identity Unlocks at Scale [16:11] World ID 4.0 and the New Architecture for Key Management [17:56] Coupon Fraud, Free Trial Abuse, and Why This Is the Baseline Problem [19:50] How Agents Should Interface Differently Than Humans [21:00] The Coinbase and Cloudflare Partnership: Micro-Payments and Bot Rate-Limiting [21:48] Agent Delegation: Which Human Is Behind These Hundred Bots? [24:37] Government Use Cases, Polling, and Community Verification [25:13] Tinder, Gaming, Dating, and the Places Certainty Changes Everything [27:18] Painting the Picture: What Life Looks Like with 100 Agents Working for You [29:17] Mobile-First Parallels and What AI Natives Will Look Like [31:14] The Downside Is Real But the Upside Is Bigger [33:36] The Future in Two Words: Builders and Abundance [35:20] How to Learn More and Connect with Ajay Connect with Ajay Patel LinkedIn: https://www.linkedin.com/in/ajayppatel/ Wesite: https://www.world.org Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  • April 2 · 42 min

    When Agents Write the Code with Taskrabbit CTO Scott Porad

    In this episode of the Shift AI Podcast, Scott Porad, CTO at TaskRabbit, joins host Boaz Ashkenazy for a wide-ranging conversation on how AI is reshaping software engineering and the future of technology leadership. Scott shares his career journey across some of the internet's earliest gig marketplaces from Rover to Dolly to TaskRabbit and how TaskRabbit's relationship with parent company IKEA came about from a simple observation: people were using the platform to assemble furniture. From there, the conversation dives deep into how AI coding tools have swept through engineering organizations, tracing the evolution from early skepticism to prompt engineering to plan mode to today's spec-driven development. The conversation explores how TaskRabbit is using AI agents for code review, the challenge of adapting AI to legacy codebases, and what happens when designers and product managers can write code themselves. Scott addresses the blurring of roles and decision rights across engineering teams, the shadow IT challenge of citizen developers building internal tools with lovable.dev and similar platforms, and why security — unlike everything else — is a one-way door that can't be undone with people and money. This episode is essential listening for engineering leaders, product managers, and anyone trying to understand how the practice of building software is being fundamentally rewritten in real time. Chapters Connect with Scott Porad LinkedIn: https://www.linkedin.com/in/scottporad/ Podcast: howmanyctos.com Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  • March 17 · 17 min

    Conversation and Context Define the Future of Commerce with Salesforce CMO Commerce Gordon Evans

    In this episode of the Shift AI Podcast, Gordon Evans, CMO of Commerce Cloud at Salesforce, joins host Boaz Ashkenazy live from Dreamforce in San Francisco for a conversation on how AI agents are reshaping commerce across both B2C and B2B. Gordon breaks down the full scope of Salesforce’s commerce portfolio—from the well-known B2C platform powering brands like Pandora and L’Oréal, to B2B commerce, order management, and the recently acquired PredictSpring point-of-sale capability. Together, these pieces deliver what Salesforce calls unified commerce: the same product, inventory, and customer view whether you’re engaging online or in-store. The conversation dives into how AgentForce Commerce is bringing AI-powered personalization to retail. Gordon shares how Pandora’s Gemma agent has driven a 10% increase in NPS by handling customer service with the nuance of a knowledgeable store associate, and how Williams Sonoma’s Olive agent helps shoppers plan everything from Thanksgiving dinner to table decor. The discussion explores why great data is the foundation for effective agents, how B2B buyers deserve the same seamless experience as consumers, and why natural language interfaces are collapsing the technical barrier between businesses and their customers. Boaz and Gordon also examine the evolving trust dynamic around AI in commerce—how the pandemic accelerated consumer willingness to trade data for speed and convenience, and how that same value exchange is now driving adoption of AI agents. Gordon shares how his own team uses internal LLMs and Slack bots to move faster, and why learning to ask the right questions is becoming the most important professional skill. This episode is essential listening for commerce leaders, retail strategists, and product teams who want to understand how AI agents are moving beyond customer service into full shopping experiences—and why conversation and context are the two words that define what comes next. Chapters [00:00] What It Means to Be CMO of Commerce at Salesforce [02:15] AgentForce Commerce and the Unified Commerce Vision [03:37] PredictSpring, Point of Sale, and Bringing It All Together [04:20] Personalization Powered by Data and AI Agents [05:58] Why B2B Buyers Deserve the Same Experience as Consumers [07:30] First Job, Worst Job with Gordon Evans [09:30] How AI Tools Are Changing the Daily Work of Marketing [11:20] Pandora, Williams Sonoma, and the Rise of Brand Agents [13:50] Trust, Credit Cards, and the Speed-Convenience Value Exchange [15:00] Two Words for the Future of Work: Conversational and Context Connect Connect with Gordon Evans LinkedIn: https://www.linkedin.com/in/gordonmevans/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  • March 11 · 20 min

    The Revolutionary Mindset Transforming Government with Salesforce Global AI GTM Leader Nadia Hansen

    In this episode of the Shift AI Podcast, Nadia Hansen, Global AI Go-To-Market Leader and Industry Advisor for Public Sector at Salesforce, joins host Boaz Ashkenazy for a live conversation recorded at Dreamforce in San Francisco on how AI agents are fundamentally reshaping government services. Nadia shares her unconventional career journey—from serving as the Chief Information Officer for Clark County in Las Vegas overseeing 2.3 million residents and 10,000 employees, to leading public sector go-to-market strategy at Salesforce. From there, the discussion dives deep into how today’s government agencies are navigating digital transformation with resilience, experimentation, and a growing openness to AI-driven innovation. The conversation explores how AgentForce and agentic AI are enabling government agencies to deliver seamless digital front doors for residents—automating intake processes, streamlining permit requests, breaking down departmental silos, and providing multilingual access to public services. Nadia explains why voice technology is poised to become the next major interface for government, how co-creating AI use cases with employees drives real adoption, and why the biggest barrier to transformation is mindset, not technology. Boaz and Nadia also examine the growing challenge of shadow AI in government, why bottom-up adoption workshops outperform top-down mandates, and how cities like Kyle, Texas are experimenting with AI in safe, compliant environments. The episode closes with Nadia’s powerful two-word vision for the future of work: revolutionary mindset. This episode is essential listening for public sector leaders, civic technologists, and anyone who wants to understand how AI is moving beyond individual productivity gains to transform the way government serves its communities. Chapters [00:00] From Home Depot to the C-Suite: Nadia’s Career Journey [04:07] Landing at Salesforce and Repositioning CRM for Government [07:50] First and Worst Jobs: Lessons from Selling Manure [10:22] The Digital Front Door: Seamless Government Services [12:37] Selling to Government: Speak in Outcomes, Not Products [15:03] AgentForce and the Rise of Voice-First Government [17:24] Augmentation Over Replacement: Addressing the Fear of AI [19:47] Bottom-Up Adoption: Co-Creating AI Use Cases with Employees [21:13] Public Safety, Multilingual Access, and the World Cup [23:30] The Future of Work: Revolutionary Mindset Connect with Nadia Hansen LinkedIn: https://www.linkedin.com/in/nadiakhansen/ Newsletter: Hack to the Future (on LinkedIn) Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  • February 21 · 34 min

    Securing Agentic Automation in the Enterprise with UiPath CISO Scott Roberts

    In this episode of the Shift AI Podcast, Scott Roberts, CISO at UiPath, joins host Boaz Ashkenazy for a deep dive into how agentic AI is reshaping enterprise security and automation—both for customers and inside UiPath itself.Scott shares his 25-year security journey spanning Microsoft’s early Security Response Center days (including the era that produced Patch Tuesday and the Security Development Lifecycle), product security work across Windows and Xbox, time at AWS, and leadership roles at Google where he helped build the Android Security Assurance and Pixel Security teams and the Android Monthly Security Update process. He also discusses his work in security standards across IPsec, HTML5 encrypted media, GSMA device security, and most recently, contributions to emerging agentic AI security standards.The conversation then explores UiPath’s evolution from traditional RPA into a unified platform that combines deterministic automation with agentic workflows. Scott walks through a real-world healthcare billing example where agentic automation increased deduplication accuracy dramatically by handling complex, variable inputs that classic RPA struggled with—while still keeping humans in the loop and feeding outcomes back into the system to improve over time.Boaz and Scott go deep on what’s changed for CISOs in the post-LLM world: the need for guardrails, identity and entitlements for AI agents, and the challenge of end users copying sensitive information into consumer AI tools. Scott explains UiPath’s approach: enable adoption while using nudges and policy controls to redirect sensitive workflows into enterprise-safe environments rather than relying solely on blocks.The episode closes with an eye-opening look at UiPath’s internal “agentic threat analyst” system—an orchestration of 60+ agents that can investigate SIEM alerts end-to-end, generate structured incident writeups, and compress hours of analyst work into roughly a minute and a half. Scott’s future-looking takeaway: as AI models evolve beyond “read-only” into potentially “read-write” systems that can update their foundational knowledge, the acceleration could be truly mind-blowing.This episode is essential listening for security leaders, enterprise operators, and automation teams trying to understand how agentic systems change not just productivity, but the entire security operating model.Chapters[00:01] Scott’s Security Journey: Microsoft, Google, Coinbase, UiPath[01:33] Security Standards Work: From IPsec to Agentic AI Standards[04:08] What UiPath Does: Process Orchestration, RPA, and Enterprise Automation[06:28] RPA vs Agentic Automation: A Healthcare Billing Deduplication Example[09:17] The Agentic Stack: Canvas, Guardrails, and the AI Trust Layer[10:31] How LLMs Change Security: Data Controls, Access, and Governance[12:14] Internal Adoption at UiPath: AI Tooling by Persona (Legal, Finance, Engineering)[13:13] Code Velocity and Security: Agents Generating Code, Agents Verifying It[15:53] Two AI Security Worlds: Orchestration Platforms vs End-User Chat Interfaces[17:11] Securing End Users: Enterprise LLMs, Nudges, and Browser-Based Controls[19:07] Sovereign AI and Data Boundaries: Keeping Data in the Right Region[21:00] Over-Permissioning Meets Agents: Why AI Makes Old Problems Obvious Fast[22:21] The Next Wave: AI Transforming the Entire SDLC End-to-End[24:53] Security Pitfalls in Agentic SDLC: Misaligned Incentives and Permissions[26:02] UiPath’s Agentic Threat Analyst: 60+ Agents, SIEM to Writeup Automation[30:07] What Changes for Humans: Faster “Time to Truth” and Higher-Leverage Work[32:09] Two-Word Future: “Mind Blowing” and Read/Write ModelsConnect with Scott RobertsLinkedIn: https://www.linkedin.com/in/scottroberts6/Connect with Boaz AshkenazyLinkedIn: https://www.linkedin.com/in/boazashkenazy/Email: info@shiftai.fm

  • February 13 · 26 min

    AI Policy and the Future of Small Business with SBA Chief Counsel Casey Bryant Mulligan

    In this episode of the Shift AI Podcast, Casey Mulligan—former Chief Economist of the White House Council of Economic Advisers and current Chief Counsel for Advocacy at the U.S. Small Business Administration—joins Boaz Ashkenazy for a timely conversation on how AI is reshaping small businesses, regulation, and the broader labor market. Casey shares his path from University of Chicago professor to serving in two presidential administrations, where he introduced automated reasoning tools into economic policy work well before the rise of large language models. He explains how his office now uses AI to review thousands of federal regulations and ensure small business voices are represented in Washington. The discussion explores accelerating AI adoption among small firms, the recent surge in new business formation, and why smaller companies may benefit more from AI than large incumbents. Casey also addresses concerns about job displacement, drawing lessons from past waves of automation and outlining why he believes the long-term impact will be increased productivity and opportunity. The episode closes with a forward-looking perspective on education, entrepreneurship, and why the “human touch” will remain a critical advantage in the future of work. Chapters [00:00] From University of Chicago to the White House[03:05] Advocating for Small Businesses in Washington[07:29] AI and the Labor Market: Lessons from Economic History[12:14] The Startup Surge and Small Business Formation[13:48] Using AI Inside the Federal Government[17:20] Vibe Coding, APIs, and Custom Productivity Tools[18:07] Automated Reasoning and Microsoft’s Z3[21:23] AI in Education and Learning[24:31] Two Words for the Future of Work: Human Touch Connect with Casey Bryant Mulligan LinkedIn: https://www.linkedin.com/in/casey-bryant-mulligan/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

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