Shift AI

Boaz Ashkenazy

Shift AI explores how AI and ML is changing the way that we work in the digital age. The show's creator Boaz Ashkenazy interviews thought leaders who are redefining how businesses and employees will be impacted by emerging technology today and in the future | Visit shiftaipodcast.com

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Sunday · 34 min
Building Private Cloud Foundations for the Agentic Era with Broadcom and VMware's Sabina Anja
In this episode of Shift AI, Sabina Anja, Chief Technologist at VMware by Broadcom, joins host Boaz Ashkenazy for a wide-ranging conversation on why private, flexible infrastructure is becoming the foundation enterprises need for the agentic era. Sabina makes the case that most infrastructure and security thinking was built for a world where humans approve every step, and that world is already gone. An assistant waits for you. An agent, in her words, gets set loose and just goes. So what happens when nobody notices an agent doing something it was technically allowed to do, but shouldn't have? Sabina has a way of thinking about that question that most infrastructure teams haven't caught up to yet. This episode is for CIOs, CTOs, VPs of infrastructure, platform engineers, and security leaders who are trying to figure out what their environments need to look like before agents are running unsupervised inside them. Chapters [00:00] Welcome and introducing Sabina Anja [00:31] From Belgium to self-taught programmer: Sabina's first jobs [04:29] Why programming hygiene still matters with Cursor and Claude Code [06:24] Virtualization then and now: from vCPUs to vGPUs [08:52] What businesses are really asking for as AI costs spike [10:46] Inside NVMe tiering and the memory crunch [13:28] Private AI and the return of sovereign infrastructure [15:43] Data ownership, geopolitics, and the new value of stolen IP [17:48] Open source, small language models, and fit-for-purpose compute [20:59] Advice for CIOs: build flexible foundations, not two-year projects [24:40] Agents vs. assistants: why blast radius changes everything [27:26] Agentic security, guardrails, and the two words: platform matters, earned trust Connect with Sabina Anja LinkedIn: https://www.linkedin.com/in/sabinaanja/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
Wednesday · 58 min
Foundation Models Go Vertical with leaders from Open AI, Mistral, Clarify and Oumi
In this episode of Shift AI, Manos, CEO of Umi, Patrick Thompson, CEO of Clarify, Brian Hall, CMO of Mistral AI, and Ben Gaffney, Deputy General Counsel at OpenAI, join host Boaz Ashkenazy for a live panel recorded at Seattle Tech Week on who actually owns intelligence in the enterprise AI era. One panelist argues that any enterprise still treating a frontier model as its core intelligence layer is renting something it should own, and predicts that in two years we'll look back at CTOs defending that approach the way we look back at driving a Ferrari to the grocery store. Another panelist, sitting inside one of the most closely watched policy fights in AI right now, explains why the debate over open source models and national security is getting a lot less theoretical, and a lot more real, by the month. This one is for CTOs and CIOs deciding whether to build or rent their AI stack, product leaders at vertical AI startups thinking about fine-tuning their own models, and anyone tracking the open source AI security and policy debate. Chapters [00:00] Welcome and thanks to sponsors JP Morgan and Ascend [01:30] Introducing the panel: Manos, Patrick, Brian, and Ben [03:54] From foundation model hype to vertical AI, what actually changed [07:37] How Clarify balances owning the system of record with using frontier models [09:44] Rising model bills, local models, and the push toward open weights [11:30] Mistral AI, sovereign AI, and why owning your intelligence matters [14:32] Data retention, training, and what the privacy debate is really about [19:10] Chinese open models, national security, and the safety debate [26:18] Why fine-tuning beats prompting for real vertical AI companies [30:43] What enterprises actually want from foundation models right now [35:35] What CIOs and CTOs will laugh about in two years [44:47] The hundred million dollar question: where the panel would invest [51:44] Advice for a 22-year-old about to spend ten years building something [53:31] What each panelist is most excited about in AI's future Connect with the Panelists Manos (Umi) - https://www.linkedin.com/in/koukoumidis/ Patrick Thompson (Clarify) - https://www.linkedin.com/in/patrickt010/ Brian Hall (Mistral AI) - https://www.linkedin.com/in/brhall/ Ben Gaffney (OpenAI) - https://www.linkedin.com/in/bengaffney/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
August 25 · 19 min
Securing Identity in the Age of Agents with Newcore CEO Zohar Alon
In this episode of Shift AI, Zohar Alon, CEO and Co-Founder of Newcore, joins host Boaz Ashkenazy live from Black Hat 2026 for a conversation on why identity, not infrastructure, is the real fault line in agentic AI. Zohar has spent thirty years watching the same problem resurface in a new costume, from VPNs to IDPs to now agents that can act on your behalf for hours at a time. He describes a system where a single trusted identity point can unlock hundreds of connected apps, and where an AI agent chasing a vague instruction might decide, on its own, to read six months of email or start testing messages against real people to get results. What happens when you can't fully predict what the agent will try next, and the guardrails have to be built for that uncertainty rather than against it, is the question Zohar has built a company around. This one is for CISOs, identity and access management leads, platform engineers building with autonomous agents, and founders working in enterprise security who need to think past service accounts and static permissions. Chapters [00:00] Welcome to Shift AI, live from Black Hat 2026 [00:25] Thirty years in cyber, from Check Point employee 55 to founder [01:30] Founding Dome9 and convincing the world the cloud needed securing [02:25] The identity problem that never got solved, from VPNs to modern IDPs [04:50] Building Newcore: one identity fabric for humans and agents [06:15] Why a single IDP becomes a single point of catastrophic risk [07:13] Pilot school, electronics class, and Zohar's path into Check Point [09:36] Mentoring the next generation of Israeli cyber founders [10:45] Why an AI agent isn't a service account [11:59] Inside an agent's "creative" pursuit of a goal [14:10] Human-in-the-loop as protection, not friction [16:35] The closing two words: unknown unknown Connect with Zohar Alon LinkedIn: https://www.linkedin.com/in/zoharalon/ Company: Newcore -https://newcore.com/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
August 8 · 41 min
Rethinking Security Analytics with In-Place Intelligence, CEO of Vega, Shay Sandler
In this episode of Shift AI, Shay Sandler, CEO and co-founder of Vega, joins host Boaz Ashkenazy for a wide-ranging conversation on why the legacy SIEM is breaking down just as security teams need their data the most. Shay grew up in Israel studying math and physics in a famously competitive class of gifted kids, then spent six years in one of the country's most elite military intelligence units before joining Granulate, a cloud cost optimization company, as one of its first ten employees. Granulate was acquired by Intel for $650 million, and after a year inside Intel, Shay left with his former Granulate colleague Ellie to found Vega — a decision he says was pushed forward by a month of reserve duty after October 7th that reminded him how much he missed solving hard problems with his old team. The two dig into why traditional SIEMs, built for a pre-cloud world of centralized data, are collapsing under multi-cloud, multi-region, siloed telemetry — and why teams that once filtered data down to save on SIEM costs now need all of it to keep up with threat actors wielding frontier models. Shay walks through Vega's architecture: querying data in place in commodity storage like S3, federating across regions and clouds without duplication or egress costs, and a deterministic, auditable natural-language-to-KQL layer that lets AI agents run threat hunts a human could fully verify. This episode is for CISOs, security operations leaders, detection engineers, and startup founders building in cybersecurity who want to understand how AI-native architecture, not just AI features, is reshaping enterprise security. Chapters [00:00] Introduction: Shay Sandler's path to founding and leading Vega [02:07] Growing up gifted in math and physics, and finding cybersecurity [04:18] Six years in an elite Israeli intelligence unit, and the "everything is solvable" mindset [06:08] First paid job at 14: distributing meat before dawn in southern Israel [08:37] Granulate, the $650 million Intel acquisition, and missing the startup thrill [10:43] October 7th reserve duty and the spark to build Vega with co-founder Ellie [15:04] How legacy SIEM broke under multi-cloud, siloed security data [17:32] The post-Mythos era: frontier models as tools for threat actors [23:16] Vega's three primitives: commodity storage, federation, and an AI-native interface [27:50] Natural language to KQL as a transparent, auditable layer for AI agents [30:05] AI as a "scalable engineering capability" for lean security teams [36:40] Velocity as the new core metric, and the closing thought: creativity and engineering Connect with Shay Sandler LinkedIn: https://www.linkedin.com/in/shay-sandler-305508107/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: boaz@shiftai.fm
July 28 · 36 min
Governing Agent-to-Agent Trust at Scale with MuleSoft from Salesforce SVP and GM Andrew Comstock
In this episode of Shift AI, Andrew Comstock, Senior Vice President and General Manager of MuleSoft from Salesforce, joins host Boaz Ashkenazy for a wide-ranging conversation on governing, securing, and controlling the cost of agentic AI at enterprise scale. The conversation covers how MuleSoft's API-led integration playbook, built during the on-prem-to-cloud shift, is now extending into what the company calls Agent Fabric — bringing governance and controlled connectivity to agent-to-agent communication. Andrew walks through a concrete example of how two internal agents trusting each other by default can leak a customer's order history, and digs into prompt injection, impersonation, and why the security industry's people-focused compliance frameworks now have to account for reasoning software, not just people. He and Boaz also get into token economics, LLM gateways, intent-based routing between local and cloud models, and the emerging trend of companies repatriating some AI workloads on-premise. This episode is essential listening for CTOs, CISOs, platform and integration engineers, and IT and product leaders responsible for governing AI spend and agent security as their organizations scale past pilot projects into production. Chapters [00:01] Andrew Comstock's path to MuleSoft [02:06] First job: tax returns and trumpet reeds [03:21] What MuleSoft does and its extension into Agent Fabric [05:29] From consumer chatbots to enterprise agent connectors [07:22] Governance and security at the enterprise level [10:36] A real example: how two agents can leak an order number [13:45] Connect AI 2025 vs. 2026 — a year of night-and-day change [16:28] Mythos, Fable, and preparing for the LLM that breaks your systems [18:11] Token economics and the true cost of enterprise AI [20:38] The "AI savior" pattern vs. applying IT discipline to AI [22:40] Hybrid deployments, local models, and intent-based routing [27:13] Why AI's uneven acceleration makes prioritization more valuable [28:57] The two-word answer: "coming soon" Connect with Andrew Comstock LinkedIn: https://www.linkedin.com/in/andrewcomstock/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
July 25 · 25 min
Teaching Discernment in the Age of AI and Higher Education with UW Vice Provost for AI Noah Smith
In this episode of Shift AI, Noah Smith, Vice Provost for AI at the University of Washington and Senior Director of NLP Research at the Allen Institute for AI, joins host Boaz Ashkenazy for a wide ranging conversation on how universities are preparing for a workplace increasingly run by AI agents. Noah's path wound from a PhD at Johns Hopkins to a tenured professorship at Carnegie Mellon, until a call from UW pulled him west in 2015 to help build out its natural language processing faculty. A few years later he took on a second role leading a research team at the Allen Institute for AI, and this past November added a newly created role as UW's first Vice Provost for AI. The conversation covers how faculty across UW are experimenting with AI in the classroom, from an interactive logic textbook in the philosophy department to new AI literacy courses, and digs into OLMo, the fully open language model project Noah leads at Ai2, unpacking why releasing the weights, code, and training data together, not just an API, matters for regulated industries, universities, and anyone who wants to retrain a model rather than just prompt it. Noah lays out a scenario where 80 percent of entry level work gets done by autonomous agents and argues the skill universities need to double down on is not AI literacy so much as discernment, the ability to unwrap a problem and figure out what questions to ask. This one is for university administrators, provosts, and faculty grappling with AI policy, as well as founders and engineers building on open source models, and anyone curious how a major research university is trying to get ahead of the agentic era instead of just reacting to it. Chapters [00:05] Welcome to Shift AI, live from UW's Foster School of Business [03:44] Noah's path from Carnegie Mellon to UW's Vice Provost for AI [06:08] Bagging groceries: Noah's first paid job [08:11] Six months in: what surprised Noah most about the role [09:22] How AI is reshaping teaching and pedagogy at UW [11:33] Preparing students for a world where agents do 80 percent of the work [14:08] Inside the Allen Institute for AI and the origins of OLMo [15:52] What "fully open" really means for language models [17:49] Specialized models versus general-purpose models for regulated industries [19:47] AI governance, security, and UW's new governance committee [24:35] The future of work in two words: human agency Connect with Noah Smith LinkedIn: https://www.linkedin.com/in/noah-smith-0322511a4/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
July 16 · 35 min
The End of DevOps and the Rise of Autonomous Cloud with Hyphen AI CEO Jared Wray
In this episode of Shift AI, Jared Wray, CEO and co-founder of Hyphen, joins host Boaz Ashkenazy for a wide-ranging conversation on how AI is poised to eliminate the complexity of cloud infrastructure and the DevOps role entirely. Jared shares his unconventional career journey from growing up in a small town in Idaho, where technology barely existed, to washing dishes at 15, teaching himself programming at the local ISP, and eventually founding five startups across cloud computing, energy tech, and developer infrastructure. From bootstrapping Tier 3 (acquired by CenturyLink) to co-founding Palmetto, now one of the largest energy lenders in the nation, Jared's path has been defined by a passion for solving infrastructure problems. The conversation dives deep into why DevOps has become painfully complex, with developers needing to glue together seven to thirteen different services just to deploy a single application across providers like AWS, Google Cloud, and Cloudflare. Jared explains how Hyphen is using AI to abstract away this complexity by asking developers only for business rules like uptime requirements and performance needs, then letting the AI determine the right architecture, deploy it, and operate it autonomously. Boaz and Jared explore why tools like Claude Code and other coding agents still cannot handle the full deployment lifecycle, what it would look like if AI agents replaced PagerDuty by calling you during an outage with a diagnosis and recommendation, and why the future of infrastructure is an autonomous cloud where humans are decision makers and agents handle everything else. The episode closes with a forward-looking discussion on agent-only companies, the death of cloud certifications, and why Jared believes DevOps was a good idea that we ran too long. This episode is essential listening for CTOs, platform engineers, and startup founders who want to understand how AI is moving beyond writing code to fundamentally transforming how software is deployed, operated, and scaled. Chapters [00:00] From Pocatello to Five Startups: Jared's Career Journey [02:49] Building Fonz, Co-founding Palmetto, and Finding Passion in Infrastructure [06:05] Why AI Led Jared Back to Infrastructure with Hyphen [07:05] First Job as a Dishwasher and Breaking Into Tech [08:46] What Is DevOps and Why Does It Exist [10:49] Why Cloud Infrastructure Has Become So Painfully Complex [12:36] How AI Can Apply Best Practices Without Reinventing the Wheel [14:35] The Hyphen Developer Experience: Business Rules Over Architecture [17:14] Why Claude Code and Coding Agents Cannot Solve Infrastructure Yet [20:26] The Full Context Problem: Operating Across Multiple Cloud Providers [23:07] Autonomous Cloud: When Agents Talk to Agents [24:17] Replacing PagerDuty: AI Agents That Call You During Outages [28:47] March Madness, Live Streaming, and Why Five Minutes Feels Like a Lifetime [30:59] Two Words for the Future of Work: Autonomous Cloud [33:20] Agent-Only Companies and Why Humans Will Be CEOs [35:12] DevOps Was a Good Idea We Ran Too Long [35:41] What Is Next for Hyphen Connect with Jared Wray LinkedIn: https://www.linkedin.com/in/jaredwray/ Email: jw@hyphen.ai Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
July 7 · 38 min
The Case for Deterministic AI with Logical Intelligence CSO Patrick Hillmann
In this episode of Shift AI, Patrick Hillmann, Chief Strategy Officer at Logical Intelligence, joins host Boaz Ashkenazy for a conversation about why the next era of AI cannot be built on probability alone. Patrick shares his unconventional path into AI, from crisis communications and cybersecurity work at Edelman and General Electric, to steering Binance through its most turbulent years and a major DOJ settlement. At Logical Intelligence, Patrick now works alongside Yann LeCun, a Fields Medalist, and engineers from Meta, Google, and Cruise to build deterministic, energy-based reasoning models. Patrick explains why LLMs behave like a confident intern, fast and articulate, but wrong in ways you only catch if you already know the answer, and why critical systems like power grids, hospitals, and self-driving cars need a layer of certainty that probabilistic systems cannot provide. He and Boaz dig into Logical Intelligence's benchmark results, including a 98% score on the notoriously difficult Putnam math competition, and a public Sudoku test where their energy-based model, Kona, beat every major LLM combined while running on a fraction of the compute cost. This episode is essential listening for CTOs, technical leaders, and anyone trying to understand what comes after the current generation of large language models. Chapters [00:00] Patrick's Improbable Path: From Grad School to the Front Lines of a Geopolitical Crisis [02:43] From Binance to Chief Strategy Officer at Logical Intelligence [02:54] The First Paid Job: Unloading UPS Trucks in 100 Degree Heat [04:31] The UPS Lesson That Still Shapes How He Thinks About Work [04:47] Why LLMs Are Confident Guessing Machines, Not Truth Machines [07:14] The Team Behind Logical Intelligence: A Fields Medalist, Yann LeCun, and Math Olympiad Engineers [08:55] Is Logical Intelligence Betting Against LLMs? [10:32] The AI Sandwich: Where LLMs, Reasoning Layers, and World Models Fit [12:36] The Putnam Benchmark and Why Formal Proofs Don't Get Partial Credit [15:44] What Is an Energy-Based Model, Really? [19:54] Eve Badia's 15-Year Path to the Energy-Based Reasoning Model [22:04] Formal Verification and the Future of Secure Code Generation [23:33] When Unverified Code Fails: The Molson Coors Ransomware Story [25:39] Why AI Coding Tools Create Rat's Nests Engineers Can't Debug [28:53] The Sudoku Test: 98% Accuracy for $4 vs $14,000 for the Leading LLMs [31:13] ByteDance, China, and the Race for Formal Methods [33:42] Two Words for the Future of AI: Chaotic Determinism [37:12] Where to Follow Logical Intelligence and Founder Eve Badia Connect with Patrick Hillmann LinkedIn: https://www.linkedin.com/in/crisiscommunications Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
June 26 · 30 min
AI, Security, and the Courage to Reinvent with Smartsheet CTO Cynthia Tee
In this episode of the Shift AI Podcast, Cynthia Tee, former CTO of Smartsheet, joins host Boaz Ashkenazy for a wide-ranging conversation on what it really takes to integrate AI at enterprise scale responsibly, securely, and in a way that earns lasting customer trust. Cynthia shares her unconventional journey from growing up in Manila and working her first job at a library at age 12, to earning a computer science degree from MIT, building her career at Microsoft, running Ada Developers Academy, and ultimately leading engineering at Smartsheet through one of its most consequential chapters, including the company's transition from public to private and the rollout of its first generation of AI-powered features. The conversation dives deep into how Smartsheet approached AI integration: using generative AI to simplify formula generation and data visualization, being deliberate about what information was and wasn't sent to LLMs, and communicating transparently with enterprise customers who needed to trust the system before they would adopt it. Cynthia explains why trust, governance, and data classification aren't afterthoughts, they're the foundation that makes AI deployment possible at scale. Boaz and Cynthia explore the emerging role of MCP in connecting LLMs like Claude to applications like Smartsheet, translating user intent into real-world action across complex workflows. They also get into what SaaS executives often underestimate: that shipping AI features is the easy part, and evolving the rest of the organization, pricing, enablement, customer support, and role definitions is where companies get stuck. The discussion turns to the next generation of workers and the genuine tension young people face between learning a craft and leaning on AI to accelerate it. Cynthia shares a perspective on hustle, curiosity, and what it looks like when someone who's never written a line of code builds an inventory system for vintage clothing because a tool like Claude made it possible. This episode is essential listening for CTOs, engineering leaders, and product executives who want to understand what responsible AI deployment actually looks like inside a company operating at scale.
June 16 · 40 min
Building the AI-First City with San Jose Chief Innovation Officer Stephen Caines
In this episode of the Shift AI Podcast, Stephen Caines, Chief Innovation Officer and Budget Director at the City of San Jose, joins host Boaz Ashkenazy for a wide-ranging conversation on how AI is reshaping city government, public services, and the workforce at one of America's most technologically ambitious cities. Stephen shares his unconventional path from pre-med at Case Western to digital privacy law at the University of Miami, a Stanford fellowship researching surveillance AI ethics, and ultimately landing at San Jose's Mayor's Office where he now leads both innovation strategy and the city's budget. From there, the conversation dives into how San Jose is positioning itself as the AI-first city in the nation, leveraging proximity to Adobe, Cisco, Zoom, Nvidia, Apple, and Google to advance meaningful community-level change. The discussion explores the city's AI for All initiative, a public-private partnership with Anthropic, Google, and OpenAI to provide free AI education to residents and city employees alike. Stephen walks through the city's dual-track upskilling program, its approach to employee training that is purposely non-mandatory, and how San Jose is balancing top-down innovation mandates with bottom-up experimentation. Boaz and Stephen also dig into real-world deployments: object detection cameras on fleet vehicles that proactively identify potholes and road hazards before residents report them, AI translation tools expanding Spanish and Vietnamese participation in city council meetings, and the 311 customer service redesign aimed at reducing resident burden while improving satisfaction. Stephen is candid about the ROI question, how to distinguish pilots worth operationalizing from ones that generate noise without value and the long-term financial risks of AI infrastructure built on VC-subsidized pricing. The episode closes with a discussion of the GovAI Coalition, a San Jose-founded network now spanning over 900 public agencies, and Stephen's two-word vision for the future of work: chronic adaptability. Chapters [00:00] From Pre-Med to Chief Innovation Officer: Stephen's Career Journey [04:12] San Jose as the AI-First City: Population, Geography, and the Lean City Challenge [07:49] Proximity as Advantage: Partnering with Anthropic, Google, OpenAI, and Nvidia [08:23] AI for All: Free Community Education and In-Person Training Sessions [11:10] Upskilling City Employees: Voluntary Training, Two Tracks, and Retention Strategy [14:38] Balancing Top-Down and Bottom-Up Innovation [16:14] The 311 Network and Customer Service Vision: A 360-Degree View of the Resident [17:13] Object Detection on Fleet Vehicles: Proactive Pothole and Road Hazard Detection [19:34] Surprising Community Feedback and the Case for Keeping Humans at the Front Door [22:04] ROI in Government: How to Evaluate Pilots and Decide What Gets Operationalized [24:24] The Hidden Costs of AI: Staffing Realignment, Drone Programs, and VC Subsidies [26:14] Building Infrastructure You Own: The Road Safety Images Database [27:24] The GovAI Coalition: 900 Public Agencies, Shared Contracts, and Peer Learning [32:04] The Future of Work in Cities: Chronic Adaptability and the Individual Journey Connect with Stephen Caines LinkedIn: https://www.linkedin.com/in/stephen-caines/ City of San Jose Innovation Hub: https://www.sanjoseca.gov/your-government/departments-offices/information-technology/city-innovation/it-innovation-hub Connect with the GovAI Coalition Website: https://www.sanjoseca.gov/your-government/departments-offices/information-technology/ai-reviews-algorithm-register/govai-coalition Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
June 9 · 33 min
Unprompted Intelligence in High-Stakes AI with Hebbia CTO Aabhas Sharma
In this episode of the Shift AI Podcast, Aabhas Sharma, CTO at Hebbia, joins host Boaz Ashkenazy for a deep conversation on what it actually takes to deploy AI in high-stakes institutional environments — and why the bar is far higher than most tools can meet. Aabhas shares his path from running engineering at Postmates through its Uber acquisition, to a five-year stint as CTO at fintech startup Found, to his current role at Hebbia which began as a year-long advisory engagement before he joined formally. From there, the conversation dives into the core problem Hebbia solves: knowledge workers at the world's top investment banks, asset managers, and private equity firms buried in thousands of documents, needing multi-step analysis that existing tools simply can't handle. The discussion covers how Hebbia thinks about the interplay between deterministic software and large language models using LLMs only where generative reasoning is truly needed and keeping everything else rules-based, auditable, and fast. Aabhas explains the company's "forward deployed banker" model, where former investment bankers and transaction lawyers embed with customers to encode each firm's unique institutional methodology into Hebbia's platform. Boaz and Aabhas also explore what trust actually means in practice in regulated industries: explainability at the clause level, consistency across runs, and deliberate human checkpoints built into every workflow. They dig into the adoption dynamics at junior versus senior levels, the governance challenges that come with agentic systems, and why earning autonomy must be incremental in high-stakes environments. The episode closes with a striking observation: firms layering AI on top of existing processes are just moving bottlenecks. The firms that will pull ahead are the ones willing to redesign the factory floor, asking what it would look like to build the organization from scratch with AI today. This episode is essential listening for enterprise technology leaders, founders building in regulated verticals, and anyone thinking seriously about the gap between individual AI productivity and firm-level outcomes. --- Chapters --- Connect with Aabhas Sharma LinkedIn: https://www.linkedin.com/in/aabhassharma/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
June 3 · 53 min
Systems Thinking is the Agentic Unlock with Google's LaSean Smith
In this episode of the Shift AI Podcast, LaSean Smith, Product and Growth Lead at Google Cloud, joins host Boaz Ashkenazy for a wide-ranging conversation on how systems thinking and agentic AI are reshaping the way individuals, small businesses, and enterprises operate. LaSean shares a career journey that spans Microsoft HoloLens, Amazon, a successful startup exit, and now Google — plus a portfolio of small businesses that have served as his real-world AI lab. From a salad shop in Renton to a pre-construction development business in Seattle, he's applied workflow design and agent automation to solve practical problems long before it was fashionable. The conversation digs deep into how to actually build effective AI agents — not by prompting a chatbot, but by thinking in workflows first, identifying where reasoning actually needs to happen, and writing skills that make agents fast, reliable, and token-efficient. LaSean explains the "parcel grader" agent he built for his construction business, why he starts every agent build in a chat interface before moving to CLI, and how the McDonald's SOP model is the right mental framework for getting great output from AI. Boaz and LaSean also discuss the barbell economy that AI is creating — where small players and large enterprises both gain leverage while the middle gets squeezed — why Microsoft's Copilot strategy missed the point, how to think about agent security and identity, and why healthy organizational culture is the actual prerequisite for successful AI adoption. The episode closes with a reflection on what "always changing" really means as a mindset, and why building resilience and systems thinking skills now is the most important career investment anyone can make. This episode is essential listening for entrepreneurs, operators, and anyone using or thinking about deploying AI agents in their work. --- Chapters [00:00] Episode 100 and LaSean's First Jobs [03:30] From Microsoft HoloLens to Amazon to Google: LaSean's Career Path [08:00] What LaSean Does at Google Cloud Today [11:00] The Entrepreneurial Side: Small Businesses as an AI Lab [16:00] The Barbell Economy: Why the Middle Is Being Squeezed [20:00] Building the Parcel Grader Agent for Pre-Construction [25:00] How to Write Better Skills: Start in Chat, Not CLI [30:00] Workflow Thinking vs. Department Thinking [35:00] Why Google Is Generating 75% of Its Code with AI [38:00] The McDonald's SOP Model for Agent Design [42:00] Agent Security for Individuals and Small Businesses [47:00] Enterprise AI: Governance, Trust, and Organizational Design [52:00] The Two-Word Future of Work: Always Changing --- Connect with LaSean Smith LinkedIn: https://www.linkedin.com/in/laseansmith/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
May 19 · 51 min
The Agentic Platform Hiding in Plain Sight with Slack Senior Director of DevRel Kurtis Kemple
In this episode of the Shift AI Podcast, Kurtis Kemple, Senior Director of Developer Relations at Slack (Salesforce), joins host Boaz Ashkenazy for a wide-ranging conversation on how Slackbot is evolving into a full agentic platform for human-AI collaboration in the flow of work. Kurtis shares his extraordinary personal journey, from growing up in poverty in Northern New Jersey, dropping out of school, struggling with addiction, and spending over six years incarcerated, to teaching himself to code in prison with nothing but a textbook and a computer with no internet. From there, he built a career in tech that has taken him to one of the most prominent roles in developer relations at Salesforce. The conversation dives deep into how Slackbot is becoming far more than a simple assistant. Kurtis demonstrates how skills, canvases, and MCP connectors transform Slackbot into a powerful orchestration layer where multiple agents and humans collaborate in threads, channels, and workflows. He explains how Slack is positioning itself as the interface for agentic AI, whether that means connecting to Agentforce, GitHub, PagerDuty, or custom-built tools. Boaz and Kurtis explore the concept of bounded autonomy, the idea that agents should earn expanded capabilities through demonstrated consistency, much like onboarding a new employee. They discuss how ambient agents, gamified learning experiences, and personal productivity skills are already transforming day-to-day work for teams using Slack internally at Salesforce. This episode is essential listening for developers, team leads, and anyone building or deploying AI agents who wants to understand why the orchestration layer matters more than any single model, and how the future of work is being shaped inside the tools we already use every day. Chapters [00:00] From Poverty to Prison to Tech: Kurtis's Journey [04:28] Learning to Code Behind Bars with No Internet [06:39] Landing at Salesforce and Second Chances in Hiring [07:11] First Job: The Kemple Kids Shoveling Snow [08:48] The Role: Slackbot, DevRel, and the Agentic Platform Vision [11:35] Multi-Party Collaboration: Agents and Humans in Threads [12:43] Why Slack Is the Orchestration Layer for AI [15:25] Skills Deep Dive: Building and Using Custom Skills [18:32] Context from Conversations: Slack as a Living Repository [20:29] Canvases, Writing Styles, and Seamless Workflows [22:08] Customer Success Stories: Linear, Engine, and Design Partners [25:22] Human-Agent Orchestration vs. Agent-to-Agent Orchestration [28:45] Ambient Agents: The Tidy Skill and Chief of Staff [33:06] Building Trust Through Bounded Autonomy [34:22] Design Partners: Linear, GitHub, and Graceful Degradation [39:11] Slack Platform Power Up: Gamified Learning with Skills [42:37] The Future of Work: Boundedness and Agency [45:04] AI for Everyone: Small Models, Big Access, Edge Intelligence [47:08] What's Next: Slack Developer Day (May 20) and Beyond Connect with Kurtis Kemple LinkedIn: https://www.linkedin.com/in/kurtiskemple/ Email: curtiskemple@gmail.com GitHub: https://github.com/kurtiskemple Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
May 15 · 32 min
AI Agent Deployment and Real ROI with MongoDB Field CTO Pete Johnson
In this episode of the Shift AI Podcast, Pete Johnson, Field CTO of AI at MongoDB, joins host Boaz Ashkenazy for a wide-ranging conversation on where AI agents are actually delivering ROI — and what still needs to happen before enterprises can trust them with customers. Pete shares his origin story as a self-taught programmer who got his start on a TRS-80 in 1981, traces how MongoDB was born into a world of cloud, mobile, and internet that relational databases were never designed for, and explains why vector search sits at the intersection of MongoDB's document model and modern AI use cases. The conversation digs into Pete's "Customer Agent AI World Tour," where he has met with enterprises in over a dozen cities and heard a consistent message: production-grade agents are real, ROI is measurable, but the deployments are employee-facing and human in the loop. Pete explains the three things blocking the jump to customer-facing agents at scale, governance, observability, and evaluations, and why that challenge mirrors the early days of HTTPS standards for e-commerce. Boaz and Pete also explore the growing conversation around sovereign AI and on-prem inference, why Apple's edge device ecosystem may be the quiet wildcard in the infrastructure debate, and how MongoDB's Atlas platform lets organizations deploy data across 125-plus hyperscaler data centers worldwide. The episode closes with a forward-looking discussion on the future of software engineering, Werner Vogels' five skills for tomorrow's engineer, and why Pete's two-word forecast for the future of work is "not doomsday" — backed by a compelling contrast between the bank teller and the tollbooth worker as a framework for thinking about automation and job transformation. This episode is essential listening for enterprise leaders, developers, and anyone thinking seriously about where agentic AI is today versus where it is headed. Chapters [00:00] From Intellivision to TRS-80: Pete's Tech Origin Story [03:13] What MongoDB Is and Why the Document Model Matters [06:23] Joining MongoDB and the Vector Search Opportunity [07:50] What Pete Is Hearing on His AI World Tour [09:06] Why Fortune 500s Start with Employee-Facing Agents [11:11] Security, Governance, and the Three Big Blockers to Customer-Facing AI [14:29] How Software Engineering Is the Canary in the Coal Mine [16:56] Sovereign AI, On-Prem Inference, and the Cost of Tokens [20:14] The Apple Edge Device Wildcard [21:19] How MongoDB's Atlas Platform Fits a Hybrid Cloud World [23:21] Using AI Agents Is Programming in English [25:50] Werner Vogels on the Five Skills Every Engineer Will Need [27:17] The Future in Two Words: Not Doomsday [28:08] Bank Tellers vs. Tollbooth Workers: Why Most Jobs Will Level Up Connect with Pete Johnson LinkedIn: https://www.linkedin.com/in/petecj2/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
May 8 · 51 min
The Future of Food Is Already Being Farmed filmed live in Wenatchee, WA and hosted by Washington State Academy of Sciences.
In this episode of the Shift AI Podcast, Steve Mantle, Founder and CEO of Innov8.ag, Raj Khosla, Dean of the College of Agricultural, Human, and Natural Resources at Washington State University, and John Cox, soil scientist and fresh produce industry operator, join host Boaz Ashkenazy for a wide-ranging panel conversation on how AI and emerging technology are transforming agriculture from the ground up. Steve, Raj, and John each bring a distinct lens to the conversation — startup founder, academic dean, and hands-on operator — and together they paint a vivid picture of where precision agriculture has been and where it is going. The discussion opens with the human side of farming: the generational knowledge, seasonal intuition, and field-level pattern recognition that has defined agriculture for centuries. The panel also covers infrastructure realities, edge computing, rural connectivity gaps, ERP systems that still require on-premise servers, and the economic pressures pushing farmers to demand AI that delivers margin today, not in five years. The conversation closes with each guest sharing their two-word vision for the future of AI in agriculture: physical AI, bright and better, and hopeful foresight. This episode is essential listening for anyone who wants to understand how AI is moving beyond the office and into the fields, orchards, and packing houses that feed the world. A huge thanks to Washington State Academy of Sciences for including this event in their Deep Dive into AI in Agriculture and Washington State University’s AgAID Institute for organizing this event held at Wenatchee Valley College. This all wouldn't be possible without the support from the funding sponsors the Association for the Advancement of Artificial Intelligence (AAAI) and the USDA ARS. Chapters [00:00] Event Introduction and Background with Jordan Jobe of the AgAid Institute [03:50] Boaz Introduces Himself and the Shift AI Podcast [08:04] Podcast Recording Begins: Welcoming the Panel [08:48] Steve Mantle: From Irrigation Hand Lines to Innovate Ag [09:40] Raj: From a Radio Science Program in India to Precision Agriculture Dean [11:24] John Cox: From Furniture Assembly to Apple Orchards and Kyrgyzstan [13:22] The Human Side of Farming: Intuition, Resilience, and Generational Knowledge [15:10] How GPS Unlocked Precision Agriculture and Field-Level Heterogeneity [16:48] Multi-Generational Farm Knowledge as a Living Large Language Model [18:09] Notebook LM Meets the Farm: The Harvest Replay Concept [21:16] Batteryless Biodegradable Sensors and the Future of Field Diagnostics [24:30] Precision Irrigation Prescription Maps and Dynamic Field Management [26:18] Computer Vision in the Apple Packing House [27:58] AI as a Global Expert: Diagnosing Crop Disease in Kyrgyzstan [30:15] Constraints in Ag AI: Data Stacks, Fragmented Systems, and Cultural Resistance [33:50] Build vs. Buy and the Change Agent Problem in Agriculture [35:50] Edge Computing, On-Premise Servers, and Hybrid Infrastructure on the Farm [39:09] Rural Connectivity: Broadband Gaps and the Starlink Reality [41:54] Economics of Ag AI: Labor Costs, Tightening Margins, and ROI [44:28] Moving from Spreadsheets to Agents: Why Trust Is the Real Barrier [45:50] Future Skills: What the Next Generation of Farmers Needs to Know [48:05] FFA Ag Tech Innovation Day and Hands-On Learning for Students [50:07] Two Words for the Future: Physical AI, Bright and Better, Hopeful Foresight [54:15] How to Connect with Steve, Raj, and John Connect with the Guests Steve Mantle LinkedIn: https://www.linkedin.com/in/stevemantle/ Raj (Dean, WSU College of Agricultural, Human, and Natural Resources) LinkedIn: https://www.linkedin.com/in/raj-khosla-2566a819/ John Cox LinkedIn: https://www.linkedin.com/in/jonathan-cox-soildr/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
April 23 · 28 min
Agentic AI and the Future of Revenue Teams with Outreach CEO Abhijit Mitra
In this episode of the Shift AI Podcast, Abhijit Mitra, CEO of Outreach, joins host Boaz Ashkenazy for a wide-ranging conversation on how agentic AI is fundamentally reshaping the way revenue teams operate. Abhijit shares his journey from tutoring a seventh-grade student advanced math in India to spending 30 years building enterprise systems at Oracle, SAP, and ServiceNow before joining Outreach as head of product and engineering—and eventually stepping into the CEO role. From there, the discussion dives deep into how Outreach has evolved from a sales execution platform into a full agentic AI infrastructure for go-to-market workflows. The conversation explores the critical distinction between true autonomous agents and what Abhijit calls "fancy dashboards"—how Outreach's agents autonomously research accounts, personalize outreach, prep sellers for meetings, provide real-time coaching, and even submit forecasts without human intervention. Abhijit explains why the shift from SaaS seat licenses to hiring agents with skills and capacity represents the next evolution of enterprise software, and why companies that don't adapt will not survive. Boaz and Abhijit also dig into the governance challenge at the heart of enterprise AI adoption—shadow AI, role-based access control, and how to give individual sellers the autonomy to personalize their own agents while keeping everything inside trusted organizational guardrails. The episode closes with Abhijit's vision for self-adapting AI that learns best practices from every rep and distributes them across the entire team, making every rep your best rep. This episode is essential listening for sales leaders, revenue operators, and enterprise technology buyers who want to understand how agentic AI is moving beyond individual productivity tools to unlock fundamentally new go-to-market operating models. Chapters [00:00] Introduction: Abhijit's Career from Oracle and SAP to Outreach [01:26] First Job: Teaching 12th Grade Math to a 7th Grader in India [01:58] Outreach's Evolution from Sales Execution to Revenue Orchestration [03:42] 2025 Was the Launch—2026 Is When Agents Actually Happen [04:12] What Makes a True Autonomous Agent (Not a Chatbot or Dashboard) [07:46] The New Paradigm: Hiring Agents vs. Renting Software Seats [09:43] Personal Agents and the Case for Individual Autonomy [12:06] Enterprise Governance: Why Every Rep Needs Guardrails [12:34] Shadow AI, Sovereign AI, and What CISOs Are Actually Worried About [13:34] Role-Based Access Control for Agents: Match the Person, Not the Platform [14:20] Day in the Life: What Agents Do So Sellers Don't Have To [17:06] Outreach's Own 100-Person Sales Team as a Live Testing Ground [17:34] The Numbers: 39% Productivity Increase Measured Internally [19:17] Is SaaS Dead? The Real Transformation Happening in Enterprise Software [21:50] What's Next: Self-Adapting Agents That Learn and Spread Best Practices [24:30] Two Words on the Future of Work: Unleash Your Best Performance [25:38] Closing Thoughts on Augmentation, Fear, and Human Potential Connect with Abhijit Mitra LinkedIn: https://www.linkedin.com/in/mitrasaab/ Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm
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

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