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: [email protected]

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: [email protected]

In this episode of the Shift AI Podcast, Patrick Supanc, Chief Product Officer at Coursera, joins host Boaz Ashkenazy for an in-depth conversation on how AI is transforming education, workforce skills, and lifelong learning at a global scale.

Patrick shares his deeply personal and unconventional journey—from growing up as the son of two educators and immigrating to the U.S., to working in public policy at the World Bank, having a formative experience in a rural classroom in Brazil, and ultimately transitioning into education technology.

The conversation dives into how baseline AI literacy is rapidly becoming essential for everyone, not just technologists. Patrick explains how learner demand on Coursera has surged, with AI enrollments accelerating and shifting from introductory content toward more advanced topics like agentic AI, orchestration, and role-specific application of AI tools.

Boaz and Patrick explore how large language models are being integrated directly into learning experiences through Coursera Coach—an AI-powered tutor designed to deliver personalized, efficient, and high-integrity learning. Patrick outlines why memory, contextual relevance, fast feedback loops, and verified assessments are critical for adult learners who need to upskill quickly while balancing real-world constraints.

Finally, the episode looks ahead to the future of education and work, touching on global access, AI-powered translation and dubbing, voice-based interaction, role-play simulations, and the potential role of avatars. Patrick closes by framing the future as “skills-first and accessible,” underscoring Coursera’s mission to ensure that verified, job-relevant skills are available to learners everywhere.

This episode is essential listening for founders, operators, educators, and professionals who want to understand how AI is reshaping not just productivity, but the entire learning and workforce ecosystem.

Chapters

[00:00] From Educators to EdTech: Patrick’s Journey to Coursera

[04:24] AI Literacy as the New Baseline Skill

[07:18] The Rapid Rise of AI Learning Demand on Coursera

[08:17] From Intro to Agentic AI: How Learner Needs Are Evolving

[11:22] Tracking Skills at Scale with Coursera’s Career Graph

[14:31] Coursera Coach: AI Tutors, Personalization, and Memory

[17:32] Learning by Doing: Role Play, Labs, and Real-World Practice

[19:41] Anxiety, Relevance, and the Need for Continuous Upskilling

[21:31] Helping Learners Navigate an Uncertain Career Future

[24:31] Global Access: Translation, Dubbing, and Emerging Markets

[26:21] Voice, Avatars, and New Interaction Models in Learning

[28:49] Andrew Ng’s Influence on Coursera and AI in Education

[30:26] The Future of Work and Learning: Skills-First and Accessible

Connect with Patrick Supanc

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

Connect with Boaz Ashkenazy

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

Email: [email protected]

In this episode of the Shift AI Podcast, Alex Waddell, Chief Information Officer at Adobe Population Health, joins host Boaz Ashkenazy live from Dreamforce in San Francisco for a deep dive into AI adoption in one of the most highly regulated—and most impactful—industries: healthcare.

Alex shares his unconventional journey from Salesforce administrator to CIO, and how Adobe Population Health built a custom electronic medical record (EMR) on the Salesforce platform to support population health case management long before it became an industry buzzword. The conversation explores why traditional EMRs often get in the way of care—and how AI can help remove friction so clinicians can focus on patients, not paperwork.

Together, Boaz and Alex unpack how AI is being applied today to reduce clinician burnout, automate documentation, improve quality assurance, and deliver the right data at the right time. Alex also explains why “augmented intelligence,” not full automation, is the future of healthcare—and why humans will always remain at the center of care delivery.

The episode closes with a thoughtful discussion on AI adoption, clinician trust, and why involving end users directly in building AI workflows is essential for success.

This episode is a must-listen for healthcare leaders, technologists, and operators who want to understand how AI can drive real-world outcomes—not just efficiency metrics.

Key Themes & Takeaways

• Why population health required building a custom EMR from scratch

• The hidden cost of documentation and clinician burnout

• How AI can get “the system out of the way” of patient care

• Using AI for chart summarization, note generation, and QA audits

• Overcoming fear and resistance to AI in regulated environments

• Why adoption—not technology—is the real challenge

• The future of healthcare as augmented intelligence

Chapters

• [00:00] Welcome & Live from Dreamforce

• [01:30] Alex Waddell’s Journey: From Admin to CIO

• [03:39] Building a Custom EMR for Population Health

• [05:45] Data, Interoperability, and MuleSoft

• [06:45] Reducing Clinician Burnout with AI

• [08:24] Voice, Automation, and the Future of Admin Work

• [09:30] Using AI for Quality Assurance at Scale

• [10:49] AI’s Real Impact on Patient Outcomes

• [12:20] “Augmented Intelligence” and the Future of Work

• [14:00] Adoption, Trust, and Bringing Clinicians Along

• [16:00] Learning More & Closing Thoughts

Episode Quote

“An EMR doesn’t change lives. The human interaction does. AI’s job is to get out of the way so clinicians can actually care.”

Connect with the Guests

Alex WaddellChief Information Officer, Adobe Population HealthWebsite: https://www.adobepophealth.comLinkedIn: https://www.linkedin.com/in/alexander-waddell-066bb914a/

Boaz AshkenazyHost, Shift AI PodcastLinkedIn: https://www.linkedin.com/in/boazashkenazy/Email: [email protected]

In this episode of the Shift AI Podcast, Adam Alfano, Global Head of SMB at Salesforce, joins host Boaz Ashkenazy for a wide-ranging conversation on how AI agents are fundamentally reshaping small and medium-sized businesses.

Adam shares his unconventional career journey—from growing up in a steel town outside Toronto to building a global sales career and now leading Salesforce’s SMB organization. From there, the discussion dives deep into how today’s SMBs are navigating constant macro change with resilience, optimism, and an increasingly innovative mindset.

The conversation explores how agentic AI is enabling small teams to operate with enterprise-level reach—automating frontline sales development, customer service, onboarding, and even complex workflows traditionally reserved for large organizations. Adam explains why CRM platforms are becoming the operating system for human–AI collaboration, how structured data is the foundation for effective agents, and why managing AI agents increasingly looks like managing employees.

Boaz and Adam also examine the growing sense of overwhelm SMB founders feel around AI tooling, why “just help me set it up” is becoming the winning go-to-market strategy, and how natural-language interfaces are collapsing the technical barrier to adoption. The episode closes with a forward-looking discussion on avatars, workforce orchestration, and why the future of work is best described as “limitless potential.”

This episode is essential listening for founders, operators, and product leaders who want to understand how AI is moving beyond individual productivity gains to unlock entirely new operating models for small businesses.

Chapters

[00:00] From Steel Town to Salesforce: Adam’s Career Journey

[04:24] The State of SMBs: Resilience, Innovation, and Opportunity

[07:18] What Defines an SMB—and Why Size Matters Less Than Ever

[08:17] Agentic AI in Practice: Sales, Service, and Infinite Reach

[11:22] Why CRM Is Becoming the OS for Human–AI Collaboration

[14:44] Data as the Foundation: Structuring Information for AI Agents

[17:32] Lowering the Barrier: Natural Language, Vibe Coding, and Usability

[19:41] The AI Tool Overload—and How SMBs Actually Want Help

[21:31] Where AI Delivers the Biggest Near-Term Impact

[24:31] Avatars, AI Teammates, and New Interaction Models

[28:48] The Future of Work: Limitless Potential

Connect with Adam Alfano

LinkedIn: https://www.linkedin.com/in/adam-alfano-60ab329/

Connect with Boaz AshkenazyLinkedIn: https://www.linkedin.com/in/boazashkenazy/

Email: [email protected]

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

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

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

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

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

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

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

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

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

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

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

Chapters

[00:00] Introduction and Welcome

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

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

[08:45] First and Worst Jobs

[11:00] The ChatGPT Moment and AI Acceleration

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

[17:00] Three Pillars of AI Transformation

[21:15] The Rev Ops Revolution

[24:00] Enabling Sales Teams with AI

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

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

[33:45] The Platform Strategy and Integrations

[36:30] Security and Trust in Enterprise AI

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

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

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

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

Connect with Eilon Reshef

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

Connect with Boaz Ashkenazy

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

Email: [email protected]

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

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

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

Chapters

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

[03:30] Career Path Through Multiple Cities

[06:45] Growing Up in a Military Family

[09:15] First Jobs and Character Building

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

[16:30] Policy Framework and Community Trust

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

[24:45] Traffic Safety and Game Theory Applications

[28:00] Permitting Process Transformation

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

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

[38:45] Cultural Shifts and Future Vision

Connect with Rob Lloyd

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

Connect with Joe Nguyen

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

Connect with Boaz Ashkenazy

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

Email: [email protected]

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

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

Chapters

[00:00] Introduction and Welcome

[03:15] From Rocket Science to Reverse Logistics

[06:30] First Jobs and Career Journey

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

[16:20] The Problem with Current Donation Models

[19:40] Business Economics and Unit Economics

[24:15] AI Technology and Automation in Action

[29:50] The Entrepreneurial Journey and Challenges

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

[37:45] The Future of Autonomous Local Commerce

[43:20] How to Connect with Gone

Connect with Yash Wagh

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

Website: https://gone.com

Shop: https://shop.gone.com

Connect with Boaz Ashkenazy

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

Email: [email protected]

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

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

Chapters:

[00:00] Introduction and Welcome

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

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

[09:00] How AI Transformed Document Generation

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

[17:00] ROI and Multimodal Content Creation

[21:00] Advice for Deploying AI Agents

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

[28:00] Job Displacement Concerns in Europe

[30:00] Two Words for the Future

Connect with Christian Lund

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

Website: https://templafy.com

Connect with Boaz Ashkenazy

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

Email: [email protected]

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