AI Heroes & Headaches

About AI Heroes & Headaches

I’ve seen AI deliver million-dollar breakthroughs and I’ve seen it crash and burn. I’m Vivienne Wei, COO of Salesforce Unified Agentforce Platform. I’m pulling back the curtain on the wins, the flops, and the leadership calls that make or break AI transformation. Each episode, I sit down with executives and builders in the trenches of AI from unicorn founders to Fortune 100 CTOs. They’ll share what worked, what failed, and what they’d never do again. No hype. No doomscrolling. Just the unfiltered playbook for leading—and surviving—in the age of AI. Your next AI hero story or headache might be right here.

Publisher

Vivienne Wei

Category

technology

Language

en

Explicit

No

First episode

12 Aug 2025

Latest episode

13 Mar 2026

Latest episodes

14 episodes in the feed.

1. 

   13 Mar 2026

   AI Powered Strategy for CEOs to Build Flow Based, Future Ready Companies with Vala Afshar

   In this episode of AI Heroes & Headaches Podcast, host Vivienne Wei sits down with Vala Afshar, Chief Digital Evangelist at Salesforce, for a thought-provoking conversation on what it truly means to build the Agentic Enterprise. Drawing from his journey as an engineer, CMO, bestselling author, and global technology leader, Vala shares that the greatest barrier to AI transformation isn’t the technology itself, it's the siloed mindset that traps data and limits organizational flow. Through real world examples from Salesforce’s own evolution, he explains how the shift from software as a tool to software as digital labor enables enterprises to operate at unprecedented scale, eliminating “leads on the ground” and unlocking new forms of productivity. He also highlights how agentic AI can identify organizational waste and remove hidden blockages, helping companies function more like living, flow based systems where value moves efficiently across the business Expect to Learn - AI transformation succeeds when organizations dismantle siloed mindsets, allowing data to flow freely across systems so agents can operate with shared context and unlock trapped enterprise value. - Digital labor extends human capability by eliminating “leads on the ground,” scaling decision-making, and enabling hybrid human AI teams to co-create value at the speed of need. - Distinguishing waste from cost empowers leaders to use agentic AI with surgical precision identifying blockages, reallocating resources effectively, and strengthening the circulatory system of the business. - First-principles leadership transforms CEOs from “cooks” following outdated recipes into “chefs” who experiment with new AI ingredients, embrace original mistakes, and build adaptable, future-ready enterprises. Episode Highlights and Timestamps: [00:00] - Teaser[01:15] - Introduction to the Agentic EnterpriseVivienne welcomes Vala Afshar and sets the stage for discussing AI transformation, leadership, and the shift toward the Agentic Enterprise. [01:45] - Vala’s Journey: From Immigrant to Digital EvangelistVala shares his personal journey from being an immigrant refugee to an electrical engineer, CMO, and Chief Digital Evangelist at Salesforce. [05:23] - Shifting from “Capture and Protect” to Knowledge SharingVala explains how moving away from a “silo mentality” to sharing knowledge helped transform his career and led to Salesforce’s success. [07:41] - AI and Human Collaboration: Amplifying Human PotentialVala discusses how AI amplifies human capability, acting as digital labor that scales decision-making and supports employees in various roles. [08:53] - Generosity and Knowledge Sharing for Career GrowthVala reflects on how generosity, sharing knowledge, and creating transparency are key to earning respect and achieving career success. [11:34] - Trust and Transparency: Building Resilient LeadershipVala talks about how trust and transparency contribute to resilient leadership and the importance of honesty in shaping effective teams. [12:43] - Salesforce’s Culture of Belonging and FunVala shares why Salesforce’s unique culture, focused on purpose and belonging, drives employee engagement and business success. [16:53] - Anti-Silo Mindset: The Foundation of BoundlessVala explains the anti-silo mindset from his book Boundless and how it has helped organizations break barriers and unlock their full potential. [23:03] - AI in Action: Removing Blockages and Scaling OperationsVala discusses how AI-powered systems remove operational bottlenecks, allowing companies like Salesforce to scale beyond traditional human limitations. [32:29] - The Future of CEOs: Adapting to AI and First-Principles ThinkingVala advises CEOs to shift from following “recipes” to becoming chefs, embracing first-principles thinking and experimenting with new AI technologies. 🔗 Follow the Guest, Vala Afshar:👉 LinkedIn: https://www.linkedin.com/in/valaafshar 👉 Instagram: https://www.instagram.com/vafshar2012

2. 

   27 Feb 2026

   AI Success at Scale for CIOs to Achieve with Intelligent Context and Clean Data with Ravi Loganathan

   In this episode of AI Heroes & Headaches Podcast, host Vivienne Wei sits down with Ravi Loganathan, He is the EVP of Salesforce Data 360, for a compelling conversation on how enterprises can evolve toward the Agentic Enterprise where AI operates as an integrated, intelligent system embedded across business workflows. Drawing on decades of experience building distributed systems at scale, Ravi Loganathan explains why sustainable AI transformation depends on context integrity, data fluidity, governance, and strong systems thinking. Through real- world enterprise examples spanning customer support, financial services, and personalized digital experiences, he illustrates how AI, when grounded in trusted data and disciplined architecture, can elevate decision-making, enhance operational efficiency, and amplify human capability across the organization. Expect to Learn - AI becomes transformative when grounded in context integrity, ensuring agents operate with clarity of purpose, personal awareness, and trusted enterprise knowledge to deliver reliable outcomes at scale. - Intelligent personalization powered by AI elevates every interaction, dynamically adapting responses and digital experiences based on identity, intent, and real- time enterprise signals. - Systems thinking turns AI into a durable enterprise capability, with disciplined design, governance, reliability, and performance foundations that support production- grade scale. - Strategic deployment of AI agents addresses organizational scarcity of time, talent, and complexity while balancing agent economics to create measurable, sustainable business value. Episode Highlights and Timestamps: [00:00] - Teaser [01:58] - Ravi Loganathan  Career Journey and Path to Salesforce Data CloudIntroduction and set the stage for a discussion on his journey from building large-scale distributed systems to leading Salesforce Data Cloud and driving enterprise AI transformation. [04:03] - What Does Running Salesforce Data Cloud Really Mean?Simplifying the role and mission, leading to a clear articulation of how the organization helps customers better understand and serve their audiences [06:10] - What’s the Biggest AI Headache for CIOs?The conversation shifts to enterprise AI adoption, focusing on the core challenges CIOs face when moving from experimentation to production-scale deployment. [08:05] - What Does “Context” Actually Mean?Following the introduction of “context integrity,” a deeper exploration of how knowledge, persona, and judgment shape effective AI systems. [11:29] - Human Speed, Machine Scale, and System DesignBuilding on the discussion of context, the conversation moves toward scalability, examining how AI systems must extend beyond LLMs into holistic enterprise architecture. [17:08] - Intelligent Context and Making Complex Content UsefulReflecting on examples like lengthy manuals and complex documentation, highlighting the importance of structuring information to serve specific personas and objectives. [18:33] - How Does Salesforce.com Know Who I Am?Examines how AI-powered agents dynamically adapt to user identity, intent, and interaction signals to deliver personalized support experiences. [22:02] - Data Journeys, Successes, and RoadblocksThe discussion turns to enterprise execution, exploring how CIOs are navigating diverse technology stacks, data integration, and production readiness. [29:13] - Agent Economics, Silos, and Vibe Coding RisksRaises critical considerations around governance, security, agent economics, and the operational discipline required to move beyond rapid prototyping. [42:30] - The Most Overrated Trend and the Critical Skill for CIOsThe episode closes with leadership reflections on AI trends and the essential skill of systems thinking that enables sustainable enterprise impact. 🔗 Follow the Guest, Ravi Loganathan:👉 LinkedIn: https://www.linkedin.com/in/raveendrnathan 🔗 Follow the Guest’s Company:👉 LinkedIn: https://www.linkedin.com/com

3. 

   6 Feb 2026

   The Strangler Fig Strategy: Bypassing Legacy Debt to Build the Agentic Enterprise

   In this episode of AI Heroes & Headaches, host Vivienne Wei welcomes Martin Hofmann Former CIO of Volkswagen, a key leader at Salesforce and Volta Trucks, Author of The Agentic Enterprise (coming on Feb 14), Board Member and Advisor, unfiltered conversation on why most AI transformations fail before they ever scale. Drawing on decades of experience across global enterprises, high-growth technology companies, and startups, Martin challenges the prevailing “build-first” mindset and makes a compelling case for a design-led approach to agentic AI. The discussion explores why governance, trust boundaries, and expert judgment matter more than speed, how organizations can modernize without dismantling legacy systems, and why successful AI adoption is ultimately a leadership and operating-model challenge not a technology one Expect to Learn - How the 80/20 principle of agentic AI transformation spending 80% of the effort on design, governance, trust boundaries, and human-agent collaboration, and 20% on building creates the foundation for scalable, high-impact outcomes. - Why agentic AI represents an adaptive leadership opportunity, requiring organizations to evolve ownership, accountability, and operating models rather than treating agents as traditional IT tools. - How positioning AI agents as digital teammates guided by experts enables stronger collaboration between IT and line-of-business teams throughout design, testing, and continuous optimization. - Practical leadership guidance on where to start: focusing on low-risk, high-upside use cases, moving quickly once the design is right, and fostering a culture of curiosity and continuous learning Explore The Agentic Enterprise by Martin Hofmann for a design-led blueprint on scaling agentic AI with confidence. Coming on 14 February 2026:https://www.amazon.com/Agentic-Enterprise-Building-Organizations-Autonomously-ebook/dp/B0G8673JCJ Episode Highlights and Timestamps: [00:00] - Teaser [01:13] – Welcome & Framing the ConversationVivienne Wei welcomes Martin Hofmann and sets the context for agentic AI, leadership, and enterprise transformation. [01:24] – Martin Hofmann’s Journey Across Enterprise, Tech, and StartupsVivienne invites Martin to reflect on his journey from Volkswagen CIO to Salesforce SVP, startup CTO, and advisor. [03:36] – Why Operating Models and People Drive TransformationVivienne highlights the role of governance, operating models, and people in driving scalable change. [04:00] – Why Martin Wrote The Agentic EnterpriseVivienne asks what inspired Martin to write a leadership blueprint for AI-driven organizations. [06:20] – How Leaders Modernize Without Replacing Legacy SystemsVivienne asks how modern CIOs can make the leap to agentic AI while working with deep legacy environments. [08:08] – Balancing Speed and Thoughtful Design in AI AdoptionVivienne probes the risks of moving too fast or too slow in AI transformation. [11:43] – Applying the 80/20 Rule to Data and AI ReadinessVivienne reframes data readiness through the 80/20 lens and asks how leaders should approach it. [15:42] – The Agent Factory Model for Scaling Agentic AIVivienne asks how organizations can involve people and scale agentic AI effectively across teams. [23:24] – The 80/20 Leadership Principle for Agentic AI SuccessVivienne ask  Martin’s top guidance for CIOs and CEOs starting their agentic AI journey [25:44] – Closing Reflections and Where to Find the BookVivienne thanks Martin and shares where listeners can find The Agentic Enterprise. 🔗 Follow the guest, Martin Hofmann:👉 LinkedIn: https://www.linkedin.com/in/martin-hofmann-4b90405/ 🔗 Follow Guest’s Companies:Salesforce: https://www.linkedin.com/company/salesforce/ Lakestar: https://www.linkedin.com/company/lakestar-vc/ Upstream Security: https://www.linkedin.com/company/upstream-security/ Volkswagen Group: https://www.linkedin.com/company/volkswagen-group/ Volta Trucks: https://www.linkedin.com/company/voltatrucks/ 🔗

4. 

   23 Jan 2026

   How Enterprise Leaders Use Agentic AI to Transform Teams and Drive Scalable Impact with Andy White

   In this episode of AI Heroes & Headaches, host Vivienne Wei sits down with Andy White, SVP of Salesforce on Salesforce Technology, with over 16 years at the company, to explore what it really takes to drive agentic AI transformation at scale. Drawing from his experience across major acquisitions, product evolution, and enterprise leadership, Andy shares candid lessons on why AI adoption is less about technology and more about people, mindset, and change management. The conversation dives into how organizations move from traditional automation to truly autonomous AI agents, the importance of accountability and experimentation, and why curiosity and adaptability are the most critical skills in the age of digital teammates. Expect to Learn: - Why agentic AI transformation is fundamentally an adaptive leadership challenge, not a linear technology rollout. - How organizations must rethink ownership and accountability by treating AI agents as digital teammates, not IT tools. - Why successful AI adoption requires deep collaboration between IT and line-of-business teams, especially during testing and tuning. - How Salesforce prioritizes fewer, high-impact “hero agents” over agent proliferation to drive real business outcomes. -  Andy White’s advice for leaders: start with low-risk, high-upside use cases, experiment quickly, and build a culture of curiosity and continuous learning. Episode Highlights and Timestamps: [00:00] - Teaser [01:45] - Welcome & Introduction with Andy White: Vivienne Wei welcomes Andy and sets the stage for a conversation on agentic AI, leadership, and enterprise transformation. [01:55] - Andy’s Journey Through Salesforce Acquisitions: Andy shares his 16-year journey at Salesforce, including lessons learned from major acquisitions and organizational evolution. [02:55] - How Andy Evolved His Leadership for the AI Era: A discussion on how leadership mindset must shift in response to rapid AI and agentic transformation. [05:06] - Why Agentic AI Is a People Problem, Not a Tech Problem: Exploring why AI success depends more on mindset, culture, and change management than technology alone. [08:58] - Re-Engineering Teams for AI Agents: How teams must be redesigned to work effectively with AI agents as digital teammates rather than traditional tools. [11:20] - The Skills Business Leaders Need to Manage AI Agents: The new capabilities leaders must develop, including accountability, measurement, and prompt-based experimentation. [15:44] - How Leaders Should Learn Prompting and Experiment with AI: Why hands-on experimentation with AI and natural language prompting is essential for modern leaders. [21:41] - How Salesforce Decides Which AI Agents to Build: Andy explains how Salesforce prioritizes high-impact “hero agents” over agent proliferation. [28:53] - How AI Agents Unlock Capacity Humans Never Had: A look at how AI agents expand organizational capacity by handling work humans never had time to do. [31:45] - The Most Important Skills for the AI-Driven Future:Final reflections on curiosity, continuous learning, and adaptability as core skills for the future of work 🔗 Follow the guest, Andy White:👉 LinkedIn: https://www.linkedin.com/in/andy-white-8003904/ 🔗 Follow Saleforce:👉 LinkedIn: https://www.linkedin.com/company/salesforce/👉 Website: https://www.salesforce.com/in/ 🔗 Follow the host, Vivienne Wei:👉 LinkedIn: https://www.linkedin.com/in/weivivienne/👉 Website: https://www.theviviennewei.com/👉 Facebook: https://www.facebook.com/vivienne.c.wei 🔗 Listen to AI Heroes & Headaches on your favourite platform:👉 YouTube: https://www.youtube.com/@theviviennewei👉Spotify: https://open.spotify.com/show/6VdE8SqhZhhLHexxzx3gfB?si=f74b0ad0bf2549e4👉 Apple Podcast: https://podcasts.apple.com/us/podcast/ai-heroes-headaches/id1832607443

5. 

   19 Dec 2025

   AI Agent Revolution for CFOs to Reduce BPO and Boost Compliance with Anant Kale

   In this episode of AI Heroes & Headaches, host Vivienne Wei talks with Anant Kale, CEO of AppZen, an Artificial Intelligence platform for modern finance teams. With over 15 years of experience in developing complex software and a background spanning engineering, finance, and product, Anant discusses how unstructured data creates massive bottlenecks in business processes. He shares his journey from corporate planning to founding his company to solve the problem of unstructured data in finance, emphasizing the shift from automation to autonomy with AI agents. 🔑 Expect to Learn Why unstructured data is the primary bottleneck where "any process, any work, stops" in finance. How AI agents are designed to execute work autonomously, moving beyond mere assistance. The strategic value of AI for the CFO goes beyond cost savings to maximize human potential across the entire organization. How the AI Agent Studio converts existing manual work instructions (SOPs) into deployable AI agents. Anant Kale's advice to CFOs: Focus on use cases with a time to value of "weeks" and run a pilot for no more than two months. ⌛ Episode Breakdown with Timestamps [00:00:00] - Unstructured Data, The Bottleneck: Introduction to Anant Kale and the core problem of unstructured data stopping business processes. [00:01:46] - Anant's Journey & Motivation to Start: Discussing Anant's transition from structural engineering and corporate finance (Fujitsu) to founding an AI company. [00:07:48] - Building Trust in AI for Finance: The challenge of introducing nascent AI technology to a risk-averse finance organization and the importance of increasing compliance. [00:09:20] - Strategic Advantage, Beyond Cost Savings: Discussing how AI augments capability, saves money, and, more importantly, gives back time to highly compensated employees (engineers, sales). [00:14:45] - The Mental Load of Process and Policing: How AI removes the "policing" work, allowing high-value employees to focus on their core tasks and innovation. [00:16:20] - The AI Agent Studio Explained: Diving into the new Studio, which allows finance managers to convert their existing manual work instructions into autonomous AI agents. [00:22:49] - AI Agents in Finance, Accuracy and Guardrails: The need for domain-expert models (Zen realm models), deep enterprise integrations, and absolute guardrails to avoid mistakes and hallucinations in finance. [00:27:48] - Managing the AI-Native Hybrid Team: Navigating the workforce impact, creating the "AI Agent Boss" role, and setting a top-down vision to inspire transformation. [00:30:49] - CEO Recognition & The Power of Inspiration: The story of a practitioner who was called out by the CEO for leading AI agent deployment, setting an example for other teams. [00:33:17] - Final Advice: Short Time-to-Value is Key: Anant's single piece of advice to CFOs: look for areas of low risk/high ROI, and insist on a pilot with a time to value measured in weeks. 🔗 Follow the guest, Anant Kale:👉 LinkedIn: https://www.linkedin.com/in/anantkale/🔗 Follow AppZen:👉 LinkedIn: https://www.linkedin.com/company/appzen/👉 Website: https://www.appzen.com/ 🔗 Follow the host, Vivienne Wei:👉 LinkedIn: https://www.linkedin.com/in/weivivienne/👉 Website: https://www.theviviennewei.com/👉 Facebook: https://www.facebook.com/vivienne.c.wei 🔗 Listen to AI Heroes & Headaches on your favourite platform:👉 YouTube: https://www.youtube.com/@theviviennewei #AIAgents #FinanceAutomation #CFOLeadership #UnstructuredData #DigitalCoworker #FintechAI #AgentStudio #BusinessTransformation You will love this podcast if you like shows such as Founders, Acquired, Diary of a CEO, Joe Rogan and topics surrounding Elon Musk, Sam Altman, ChatGPT.

6. 

   5 Dec 2025

   30% of Underwriters Are Retiring… This CEO Says Only Data and AI Can Stop the Crisis

   In this episode of AI Heroes & Headaches, host Vivienne Wei talks with Alex Schmelkin, Founder and CEO of Sixfold, the AI platform built for insurance underwriters. Alex dissects how the wave of generative AI is forcing the traditionally slow-moving insurance industry to modernize quickly. He explains the shift from traditional risk assessment to near-autonomous underwriting agents, and why boards are asking tough questions about competitive threats. Beyond the technology, Alex emphasizes the importance of balancing AI adoption with maintaining a healthy, enjoyable work culture - stressing that fun, music, and community connection are vital for generating the creative ideas needed to navigate the AI era. 🔑 Expect to Learn Why insurance is one of the most AI-disruptible industries today. How Sixfold’s AI underwriting agents are transforming productivity for insurers. The importance of CEO involvement in successful AI transformations. How AI can be both a threat and a partner in workforce transformation. Key mistakes and lessons in rolling out AI systems within large enterprises. ⌛ Episode Breakdown with Timestamps [00:00:00] - Opening Thoughts: The Insurance Industry & AI's Tipping Point: Intro to the insurance sector's risk of stagnation and the need for transformation.[00:02:05] - Alex's Journey from Fashion to Insurtech: How Alex moved from public policy and e-commerce into founding an AI startup focused on underwriting.[00:03:30] - Founding Sixfold: The $7 Trillion Opportunity: Insight into Sixfold’s inception, vision, and mission to modernize underwriting with AI.[00:09:00] - AI Agents in Action: From Copilots to Doers: The shift from analysis-only tools to AI agents that autonomously handle underwriting tasks.[00:12:15] - Measuring Impact: Efficiency & Premium Growth: The key business metric - gross written premium per underwriter - and how Sixfold boosts it.[00:15:00] - Aging Workforce & AI as a Talent Multiplier: How AI addresses the challenge of 30% of senior underwriters retiring in the next five years.[00:17:33] - Leading Change: CEO Buy-In Is Non-Negotiable: The pivotal role of executive leadership in driving successful AI transformation.[00:20:00] - Mistakes & Learnings: Why Accuracy Measurement Matters: The early misstep of not quantifying AI accuracy and how that changed.[00:22:17] - Elevating Underwriting Managers with AI: How mid-level leaders use AI for real-time portfolio strategy and guidance.[00:25:50] - Final Thoughts: One Thing You Must Do as a Startup CEO: Alex’s top advice for AI founders and how to bring fun and balance into startup life. 🔗 Follow the guest, Alex Schmelkin:👉 LinkedIn: https://www.linkedin.com/in/schmelkin/🔗 Follow Sixfold:👉 LinkedIn: https://www.linkedin.com/company/sixfold-ai/👉 Website: https://www.sixfold.ai/ 🔗 Follow the host, Vivienne Wei:👉 LinkedIn: https://www.linkedin.com/in/weivivienne/👉 Website: https://www.theviviennewei.com/👉 Facebook: https://www.facebook.com/vivienne.c.wei 🔗 Listen to AI Heroes & Headaches on your favourite platform:👉 YouTube: https://www.youtube.com/@theviviennewei👉 Spotify: https://open.spotify.com/show/6VdE8SqhZhhLHexxzx3gfB?si=f74b0ad0bf2549e4👉 Apple Podcast: https://podcasts.apple.com/us/podcast/ai-heroes-headaches/id1832607443 #AIInInsurance #Insurtech #GenerativeAI #StartupLeadership #UnderwritingRevolution #AITransformation #VerticalAI #FutureOfWork

7. 

   7 Nov 2025

   The Psychology of Change: Why AI Adoption Starts in the Brain with Rosanne Werner

   What really drives AI transformation: technology or people? In the latest episode of AI Heroes & Headaches, I sat down with Rosanne Werner, CEO of XcelerateIQ, to unpack what truly drives transformation inside global enterprises. Rosanne has led data and culture change at Coca-Cola and now helps organizations turn AI resistance into adoption, and data into a movement. Here are a few insights that stopped me in my tracks: 1️⃣ Data is contagious. Real transformation spreads through people, not programs. A five-minute habit can start a movement. 2️⃣ Change is psychological. Four parts of the brain resist disruption — the leaders who design for safety, not fear, build faster adoption. 3️⃣ Beware “watermelon metrics.” Ninety-percent adoption may look good on a dashboard, but engagement tells the real story. 4️⃣ AI can amplify inclusion. Used thoughtfully, it gives more voices a seat at the table and helps leaders bridge personality and communication gaps.Rosanne’s perspective is a reminder that technology alone doesn’t create intelligent enterprises. Trust, curiosity, and people do. Because transformation is about more than technology: it’s about people. Listen to Episode 7 of AI Heroes & Headaches now.

8. 

   24 Oct 2025

   When Creativity Meets Technology with Alan Smithson

   What happens when a serial entrepreneur, DJ and father decides to reinvent education for the AI age? This week, I sat down with Alan Smithson, founder of Unlimited Awesome and Metavrse. From spinning records to building companies that redefine how we learn and connect, Alan’s career is a study in what happens when creativity meets exponential technology. Here are three insights that stood out: Creativity is the ultimate human edge. As AI gets faster and smarter, imagination and emotional intelligence will become our most valuable skills. The next education revolution will be experiential. Alan envisions learning that’s immersive, AI-driven, and accessible to everyone, not limited by geography, privilege, or traditional systems. Technology should create equality, not widen the gap. His mission with Unlimited Awesome is to build an economic system where innovation lifts communities rather than leaving them behind. Alan’s story reminds us that the future of AI is anbout amplifying what makes us human.

9. 

   10 Oct 2025

   Data to Profit with Vin Vashishta

   AI isn’t magic. It’s business. And according to Vin Vashishta, it's like electricity in the 1900s. On the latest episode of AI Heroes and Headaches, I sat down with @Vin Vashishta, author of Data to Profit, to explore how leaders can unlock the true value of AI. Here are a few takeaways that stood out: - From physics to AI thought leader: Vin’s journey shows how technical expertise becomes powerful when paired with business leadership. - The Data to Profit mindset: AI only matters when it creates and captures measurable business value. - Why AI is like electricity in the 1900s: the organizations that figure out how to integrate it everywhere will be the ones that win.

10. 

    26 Sept 2025

    Is Your AI Playing Chess or Checkers? with Brian Evergreen

    When it comes to your AI initiatives, is your company playing chess, or checkers? Recent reports share that only 5% of AI initiatives are successful. Why is that? According to Brian Evergreen, most companies don’t yet have a playbook for leadership in the AI era. This week on AI Heroes & Headaches, I sit down with Brian Evergreen, President of the Future Solving Club. Brian went from being an internationally competitive chess player to advising Fortune 500 CEOs on AI strategy. He has been recognized on the @Thinkers50 Radar list. His discipline and systems thinking show up in the way he frames the AI leadership challenge. In this full episode, we break down: Why incrementalism kills AI strategy The systems thinking that Brian took from chess into his professional career What an AI-first vision is, and how leaders can build it to rally their teams If you’re a leader navigating AI adoption, this conversation is full of practical lessons and bold insights.

11. 

    12 Sept 2025

    Military Precision and Machine Learning with Keith McCormick

    From Military Discipline to AI Leadership. 95% of AI pilots stall. Only 5% scale. Keith McCormick knows why. Before teaching over 1M learners on LinkedIn Learning, Keith served in the military, a foundation of discipline and clarity that he now brings to AI adoption. In Episode 3 of AI Heroes & Headaches, Keith shares why most organizations don’t fail on technology, they fail on culture. Highlights you’ll hear: - Why 95% of AI pilots stall, and what the 5% get right - Messy data = messy AI (no shortcuts here) - Culture, governance, and upskilling > hype and tooling

12. 

    29 Aug 2025

    From 1800 Flowers to InstaLILY AI with Amit Shah

    What do you actually learn running a $1.8B global brand that helps when you launch a new frontier in AI? That’s the journey of Amit Shah, Founder & CEO of InstaLILY AI and former President of 1-800-Flowers.com. 🌸 In Episode 2 of AI Heroes & Headaches, Amit and I dive into: - How scaling one of the world’s most iconic consumer brands prepared him for AI entrepreneurship - The tension between founder mode and coach mode as leaders navigate transformation - Why personalization is the real unlock, and what it means for the future of AI-powered customer connection Every hero has a headache. In AI, the two always come together.

13. 

    13 Aug 2025

    Chief Test Officer with Muralidhar Krishnaprasad

    In AI, the hardest code to crack isn’t the tech. It is leadership. For our very first AI Heroes & Headaches episode, I couldn’t have asked for a better guest than Muralidhar Krishnaprasad (MK), President & CTO of Salesforce’s Unified Agentforce Platform, one of the most authentic, game-changing leaders I’ve ever worked with. Three months ago in Hakone, Japan, I needed yen to buy a blessed souvenir. Without hesitation, MK walked hundreds of steps down to an ATM, and back up, with me. It wasn’t about money. It was about trust, respect, and showing up for people when it counts. In this episode, MK and I dive into: Why he's known as the Chief Test Officer by our team. The principle he brings from his spiritual life into his leadership. (MK and I have been to temples around the world together!) Why authenticity is a strategic advantage in the AI era. A recent rabbit hole that MK went down, just for the joy of learning. The message he wants all leaders to know. "We’re in the agentic AI era, and that’s what’s going to make the next level of transformation possible.” -MK

14. 

    12 Aug 2025

    AI Heroes & Headaches - Trailer

    I’ve seen AI deliver million-dollar breakthroughs and I’ve seen it crash and burn.I’m Vivienne Wei, COO of Salesforce Unified Agentforce Platform. I’m pulling back the curtain on the wins, the flops, and the leadership calls that make or break AI transformation.Each episode, I sit down with executives and builders in the trenches of AI from unicorn founders to Fortune 100 CTOs. They’ll share what worked, what failed, and what they’d never do again.No hype. No doomscrolling. Just the unfiltered playbook for leading—and surviving—in the age of AI.Your next AI hero story or headache might be right here.

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