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

  1. 5d ago

    Building an Agent-Native Engineering System with Github Head of Product Mario Rodriguez

    In this episode of Shift AI, Mario Rodriguez, Chief Product Officer of GitHub, joins host Boaz Ashkenazy for a wide-ranging conversation on what GitHub is becoming now that humans and AI agents build software side by side. Mario shares a number from inside GitHub's own Copilot data that cuts against the idea of a single dominant AI model, and explains why he thinks the real competition isn't happening at the model layer at all. He also lays out how GitHub is rethinking its surfaces, from Agent HQ to a tool called Spark, around a much bigger bet on where developer collaboration is headed next. This episode is for CTOs, VPs of engineering, platform and DevEx leads, and any software engineer trying to figure out where their own skills fit as more of the codebase gets written by agents. Chapters [00:00] Welcome and introducing Mario Rodriguez [00:29] From a Cuban restaurant busboy to electrical engineering to Perl [03:11] Landing at Microsoft, then GitHub after the 2018 acquisition [03:58] Redefining GitHub beyond repos: the agent-native engineering system [07:31] Staying true to developers and going model-agnostic [09:06] The Copilot usage data on model choice [10:27] Harnesses, and why the fixation on any one model is fading [13:49] Agent HQ, the GitHub Copilot app, and canvases explained [16:29] Chronicle and the continuous learning loop [18:10] Spark: lowering the floor and raising the ceiling for builders [21:35] What AI means for new versus experienced software engineers [29:09] The closing two words: fluid creativity Connect with Mario RodriguezLinkedIn: https://www.linkedin.com/in/mariorodriguez3X: https://x.com/mariorod1 Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  2. Sep 22

    Why Messy Data Is Not the AI Blocker You Think It Is with Glean Head of Product Emrecan Dogan

    In this episode of Shift AI, Emrecan Dogan, Head of Product of Glean, joins host Boaz Ashkenazy for a wide-ranging conversation on what it actually takes to give enterprise AI real organizational context. Emrecan has convinced countless CIOs and CEOs to stop chasing a data cleanup project that he says will never finish. Instead he makes the case for leaving the mess exactly where it is and solving the problem somewhere else entirely, a position that runs against nearly everything companies think they need to do before they can "get onto AI." He also lays out a theory of why knowledge workers spend half their AI time just re-teaching context, and what it would take to get that number to zero. This one is for CIOs, chief AI officers, heads of product, and platform and data leaders who are being told to fix their data before they can move on AI, and who want a second opinion. Chapters [00:00] Welcome and introduction [00:33] Emrecan's path to Glean: entrepreneur, LinkedIn, Stripe, and a warning from a VC [02:36] First paid job: fixing bikes in Turkey [04:19] What Glean actually does: the work AI platform explained [06:53] The onboarding moment of truth and losing Glean when you leave [09:40] Why organizational data, not model choice, is the real moat [10:47] Seven years of infrastructure work before the GPT moment [13:00] The pipe dream of cleaning up your data stack first [15:36] "Bot sitting": the hidden cost of teaching context to AI every day [17:59] Why picking a single model provider is one of the worst bets you can make [23:37] Token yield, marginal cost intelligence, and the "half my budget is wasted" problem [30:36] Assistants versus agents: a framework for when each one applies [36:31] What's coming next: durable, multiplayer artifacts and proactive AI [40:34] Closing question: the future of work in two words Connect with Emrecan Dogan LinkedIn: https://www.linkedin.com/in/emrecandogan/ Glean blog: glean.com Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  3. Sep 17

    Why Physical AI Is Farming's Next Frontier with Carbon Robotics CEO Paul Mikesell

    In this episode of Shift AI, Paul Mikesell, CEO of Carbon Robotics, joins host Boaz Ashkenazy for a wide-ranging conversation on how AI, lasers, and autonomy are replacing chemical weed control on farms. Carbon Robotics built a foundation model out of 150 million plant images, and Paul explains what happens when you show it a weed it has never encountered before. There's no retraining involved, and the result is something closer to a machine that understands what a plant is rather than one that's just memorized a dataset. What that actually looks like in the field, and why it took years of accumulated data to get there, is worth hearing him walk through directly. This episode is for CTOs and engineering leaders working on physical AI and robotics, agtech investors and founders, and anyone building computer vision systems that need to generalize beyond their training data. Chapters [00:01] Welcome to the show [00:31] From self-driving cars at Uber to founding Carbon Robotics [02:54] The farmer's real problem: weeds, chemicals, and health risks [04:05] Paper routes, Nintendo, and a Commodore 64: Paul's path into computing [07:59] Laser Weeder by the numbers: 15 countries and $100M+ in revenue [10:04] Inside the machine: light brighter than the sun and real-time targeting [13:33] The tractor driver bottleneck and the move to autonomy [14:55] Center pivots and near-misses: what farms teach robots that roads don't [18:40] The real moat: people, data, and years in the field [20:31] The Large Plant Model: recognizing a weed it's never seen before [24:23] Physical AI and why data is becoming the new moat [26:57] Two words for the future: autonomy and health Connect with Paul Mikesell LinkedIn: https://www.linkedin.com/in/paul-mikesell-4b63a9/ Company: carbonrobotics.com Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  4. Sep 14

    AI Agents, Identity and Enterprise Security with One Identity CEO Praerit Garg

    In this episode of Shift AI, Praerit Garg, CEO of One Identity, joins host Boaz Ashkenazy for a wide-ranging conversation on what happens to enterprise security when AI agents start outnumbering the humans they work alongside. Praerit has spent his career on both sides of this problem, from building Active Directory at Microsoft to running identity at AWS, and he says the thing keeping him up at night isn't a new category of threat at all. It's an old one moving at a speed nobody has built the guardrails for yet, and he points to a very recent, very public example of exactly how fast it can get away from you. This one's for CISOs, CTOs, platform and security engineers, and any founder scaling a company that's already handing real work to autonomous agents. Recorded Live at Baker Tily during Seattle Tech Week 2026. Thank you to Stifel Bank and Wison Sonsini for sponsoring. Chapters [00:00] Welcome back — PG's journey from Smartsheet to CEO of One Identity [01:58] What One Identity does: identity governance, explained [03:41] How the firewall evaporated and identity became the new perimeter [04:24] Rethinking identity for a world full of AI agents [07:14] Why agent identities are harder to secure than human ones [08:00] Breaking down the OpenAI and Hugging Face agent escape [09:03] Least privilege: the hardest idea in security to actually pull off [11:19] What keeps PG up at night as agents start to outnumber people [15:19] Sovereign AI, air-gapped models, and the return of on-prem [18:18] Scaling Smartsheet fast, and why flexibility beats architecture bets [20:20] What CEOs should be asking security vendors and usually aren't [22:37] The next five years: agents outnumbering humans and AI writing the code Connect with Praerit Garg LinkedIn: https://www.linkedin.com/in/praerit-garg/ Company: One Identity (oneidentity.com) Connect with Boaz Ashkenazy LinkedIn: https://www.linkedin.com/in/boazashkenazy/ Email: info@shiftai.fm

  5. Aug 30

    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

  6. Aug 26

    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

  7. Aug 25

    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

  8. Aug 8

    Rethinking Security Analytics with Vega CEO 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

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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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