Coffee With Digital Trailblazers

StarCIO Digital Trailblazer Community
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Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffee Digital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life. About the Coffee with Digital Trailblazers Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate. Topics that we cover: digital transformation, AI. genAI, AI agents, agile, DevOps, data science, data governance, IT leadership, CIO, CDO, CMO, CHRO

  1. Mental Health in the AI Era: Easing Fears About the Future of Work

    MAY 8

    Mental Health in the AI Era: Easing Fears About the Future of Work

    The episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, addressed mental health in the context of AI's impact on employment. The panel emphasized the importance of transparency, psychological safety, and ongoing learning. Key insights included the need for ethical leadership and structured AI wellness programs to ease employee concerns and enhance organizational culture. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:00:57) - CAKE: AI Burnout in the Security Industry(00:02:24) - Coffee With Digital Trailblazers(00:05:24) - How Do You Communicate AI's Impact on Your Roles?(00:06:28) - Top Executives: The Future of AI(00:09:15) - The Future of Advertising With AI(00:10:27) - The Communication Challenge of AI(00:13:55) - Cybersecurity Risk Management: AI and the Future of Work(00:15:54) - 74% of CEOs Think Their Jobs Are at Risk in AI(00:20:50) - How to communicate AI's transformative opportunity(00:22:56) - Post-Vacation Break(00:23:13) - A Team's Transformation With AI(00:27:19) - Mental Health in the AI Era(00:29:19) - What is psychological safety in our teams?(00:31:09) - Harness Your Skeptics: The Future of Creativity(00:32:24) - How to Create Psychological Safety(00:33:56) - Entry-level Jobs Being Replaced With AI(00:37:30) - Creating Psychological Safety for AI Workers(00:40:15) - Physical Safety and Psychological Safety(00:44:41) - Do We Need a Retirement Plan for AI?(00:47:12) - On Intelligence and Psychological Safety(00:50:58) - What Healthy AI Adoption Looks Like(00:54:41) - What Is Healthy AI Adoption?(00:59:17) - A message about mental health in the AI era

    1 hr
  2. AI Coding Competencies: Hype, Realities, and the Future

    APR 17

    AI Coding Competencies: Hype, Realities, and the Future

    In a recent episode of Coffee with Digital Trailblazers, Isaac Sacolick led a discussion on AI coding competencies with experts Dave Bachman and David Cassel. They examined AI development tools, emphasizing effective requirement engineering, security considerations, and the challenges of achieving artificial general intelligence (AGI), while spotlighting risks associated with AI-generated code. Chapters (00:00:01) - Coffee With Digital Trailblazers: How AI Is(00:01:26) - AI Coding Competencies(00:05:39) - Dave Bachmann on the Future of Machine Learning(00:11:08) - Coffee With Digital Trailblazers: AI Coding(00:18:39) - Citizen Development with Vibe Coding(00:22:22) - How To Manage the AI Code Development(00:26:40) - Dave and Joanne on Building AI Apps(00:31:19) - The Importance of Writing Requirements(00:32:31) - Coffee with Digital Trailblazers(00:34:25) - Cogeneration and AI on C#(00:37:14) - Does a Software Engineer Have Digital Sovereignty?(00:40:06) - Joe on the Co-Generation(00:40:30) - Will AI Replace the Devs?(00:43:41) - The Need for AI-related Skills(00:47:00) - The Future of Code is Human(00:48:03) - Best Advice for Q&A Tools for Agentix(00:53:31) - Amino vs. AI DevOps(00:55:22) - CIO Network: The Future of AI DevOps(00:56:26) - Six Rules for Leading in the AI World(00:57:44) - Hype around AGI(00:58:45) - Artificial General Intelligence (AGI)

    1h 4m
  3. Developing Your Personal Brand: Best Practices From Thought Leaders

    APR 10

    Developing Your Personal Brand: Best Practices From Thought Leaders

    This episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, features a discussion on personal branding and thought leadership in technology. Key speakers shared their experiences and best practices, emphasizing authenticity, consistency, and gradual progress in building a personal brand, likening the journey to a marathon rather than a sprint. Chapters (00:00:01) - Coffee With Digital Trailblazers(00:01:17) - A toast to Thought Leaders at the Coffee Hour(00:03:20) - A Taste of the Blog(00:04:48) - Lead From The trenches: My(00:10:07) - How to Build a Brand Through Digital Speaking(00:12:20) - CIO Network: The First Moment(00:17:38) - CIO Confessions: Personal Brand(00:21:12) - Speaking Out Loud(00:23:14) - Cyber Resilience: The 5 Ps(00:25:08) - Cyber Resilience: The challenge of communicating your message(00:28:59) - Have You Got a Brand?(00:34:19) - Developing Your Personal Brand(00:36:11) - Coffee Hour for Introverts(00:40:50) - Heather's Advice for Publishers(00:42:48) - How to Build a Brand on LinkedIn(00:47:16) - How to Build a Personal Brand(00:49:54) - Caffeine Hour: Nora's Journey(00:50:32) - What are some of the realities people should have as they're embark(00:53:59) - Derek Martin on Spelling Your Brand(00:57:05) - Writing for Social Networking(00:57:43) - How to Build a Brand with Your Friends(00:58:27) - A Week in the Life of Band(00:58:50) - AI Coding Competencies

    1 hr
  4. Managing AI Agents: New Skills, Operating Models, and Tools

    MAR 20

    Managing AI Agents: New Skills, Operating Models, and Tools

    In a recent episode of "Coffee with Digital Trailblazers," participants discussed the management of AI agents. Host Isaac Sacolick and guests debated whether organizations should treat AI agents like employees. Insights highlighted concerns over performance management approaches, emphasizing the need for governance and effective monitoring of AI capabilities. There's a growing consensus that stronger oversight frameworks are essential for the responsible deployment of AI agents in enterprises. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:01:16) - How to Manage AI Agents(00:02:26) - Will AI Agents Get the Accountability They Deserve?(00:06:10) - AI Agents Boot Camp(00:10:10) - How to Manage AI Agents(00:11:01) - Should We Manage AI Agents Like Employees?(00:15:12) - Decision Management in the AI Era(00:16:29) - Is There a Rogue AI?(00:24:41) - Should We Manage An AI Agent Like a Person?(00:29:08) - Should We Manage AI Agents? (2 Votes(00:31:22) - Coffee With Digital Trailblazers(00:33:15) - How to Monitor and Control AI Agents(00:36:30) - Are You Going to Put AI Agents Through Performance Management?(00:39:52) - How to Manage AI Agents?(00:44:03) - Security Executive Forum: Artificial Intelligence Agents and Threats(00:49:35) - Machine Learning and Continuous Testing(00:51:44) - Agile Leadership Skills, Operating Model Shift and Tech Capabilities(00:55:26) - What an AI Native Professional Looks Like(00:56:35) - AI native professionals: What's the Future of Product Management?(00:58:22) - A Taste of the 2019 Star CIO workshop on AI(00:59:53) - Add to Calendar

    1 hr
  5. National Entrepreneurship Week: Opportunities for Digital Trailblazers

    FEB 20

    National Entrepreneurship Week: Opportunities for Digital Trailblazers

    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Tyler James Johnson Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Heather May Derrick Butts Summary The episode focused on discussing entrepreneurship and the challenges of becoming a solopreneur, freelancer, or startup founder. Isaac hosted a panel of experienced entrepreneurs, including Tyler, Heather, Derek, Liz, Joanne, Martin, John, and Joe, who shared their personal stories and insights about taking the leap into entrepreneurship. The panelists discussed topics such as resilience, risk management, experimentation, and the importance of having a clear business model and market fit. They emphasized the need for networking, honest advisors, and a well-thought-out go-to-market strategy. The conversation also touched on the financial and personal challenges of entrepreneurship, including healthcare costs and work-life balance. The panelists agreed that while entrepreneurship can be rewarding, it requires careful planning, a strong support system, and a willingness to adapt and learn from failures. StarCIO Research Sources 80% of small business owners say they would still start their business if they had to do it over again. U.S. Bank Total full-time self-employment in the U.S. hit its highest annual level on record in 2025, with about 16.77 million people self-employed full-time – SBE Council Total Entrepreneurial Activity in the U.S. is at a historic high: 19% of adults are actively starting or running a new business – GEM Globally, roughly 20% of adults are involved in entrepreneurial activity, around 582–665 million people. TKG •40% see good opportunities but won’t start a business because of fear of failure Chapters (00:00:00) - Coffee With Digital Trailblazers(00:00:18) - Coffee With Digital Trailblazers(00:02:01) - National Entrepreneurship Week(00:05:02) - Coffee Hour(00:05:24) - Pivot: The Entrepreneur's Story(00:06:02) - Tell me a Story about DevOps(00:09:13) - Making the Leap: Executive Search Company(00:12:39) - Exploring the Need for Continuity in Business(00:17:47) - What Pushed You To Take The Leap?(00:20:51) - Pushing the Big Leap(00:24:34) - Pivots and the Solopreneur(00:27:50) - Solo Entrepreneur: Change of Mindset(00:29:41) - Pivoting: Small Businesses(00:33:04) - John Stamatis on Leaving His Old World(00:33:43) - The Challenge of National Entrepreneur Week(00:34:42) - Coffee With Digital Trailblazers: Cross Functional Business(00:35:24) - Culture Fit and Managing AI Agents(00:36:20) - The Essential Sales and Marketing Skills for Digital Trailblazers(00:37:28) - Greed and the Next Wave of Digital Entrepreneurs(00:41:13) - Motivation and Risk in the Continuous(00:45:15) - Exploring Opportunities, Resilience and Risk(00:47:47) - Having a Board of Advisors(00:49:19) - What is a Solopreneur's First Expense?(00:50:34) - What is the Next Wave of Digital Entrepreneurs Need?(00:53:41) - A Few More Things I Learned From Starting a Startup(00:55:37) - Martin Cowen on Work-life balance(00:56:42) - Making Sure Your Clients Are On Track(00:58:10) - 8 Essential Elements for Selection of a Startup Market(01:00:02) - Coffee World: Digital Trailblazers

    1h 2m
  6. AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys

    JAN 30

    AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys

    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Roman Dumiak Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Heather May Derrick Butts Summary The episode focused on AI-first user experiences and the challenges organizations face in transitioning to agentic AI and generative AI in customer-facing applications. Isaac led a discussion with Roman, Joanne, John, Derrick, and others about the skills and disciplines needed to develop effective AI experiences, including the importance of process engineering, cross-functional teams, and governance frameworks. The group explored how companies can test and validate AI systems, the role of architects in AI development, and the need for continuous monitoring and updating of AI models. They also discussed the potential for AI to transform customer experiences in B2C contexts, with Joanne predicting significant advancements by the end of 2026. The conversation concluded with a brief discussion about entrepreneurship and the role of AI in startup creation. StarCIO Research Sources: B2C Travel: LLM search experience by Marriott Homes & Villas. Publicis Sapient. Try it. State of Consumer AI 2025: Product Hits, Misses, and What’s Next. A16z. Try Perplexity Shop like a Pro or  Amazon Rufus. B2B software: Role-based agents in enterprise software: StarCIO Drive Transcript [00:00:00] Speaker A: Greetings, everyone. Welcome to this week’s Coffee with Digital Trailblazers, our 158th episode of speaking to digital transformation leaders around leadership, technology, AI practices, mindset, everything that goes into how we evolve our organizations. And today’s special topic. I’ve wanted to cover this for quite some... Chapters (00:00:00) - Coffee With Digital Trailblazers: AI First(00:02:28) - The future of AI in customer experiences(00:06:50) - Digital Marketing and IT: The New Disciplines(00:07:35) - What's the Need for UX Designers in the Future?(00:10:11) - What's The Gap Between AI First User Experiences and Real-(00:15:17) - What Do Organizations Need to Do to Think About AI First?(00:17:37) - Alexa & Brand Governance(00:19:24) - The Design of Human Computers(00:20:34) - AI Managers: The Need for Experts(00:21:28) - What's The Wait for an AI First User Experience?(00:24:27) - Agents and the enterprise software landscape(00:25:18) - What Do We Need to Train for AI & UX?(00:31:19) - Coffee Hours: Skill Development and AI(00:33:47) - What other areas of skill development are important for students, for recent(00:36:25) - How to Build a Culture around AI(00:38:15) - Alexa, Google, and the Librarian(00:40:07) - Six Skills for AI & Safe Innovation(00:41:54) - The Need for Specialists in AI Architecture(00:44:33) - The Need for Change Management(00:45:12) - The Need for Cross Functional Teams in AI(00:46:56) - CXO meets AI: The New Experience(00:49:19) - The AI Agent Moment(00:50:53) - B2C Innovation and Governance(00:52:27) - Governance of AI and the Future(00:54:37) - When Will We See the Alexa Siri Moment?(00:55:56) - AI Web Standards(01:00:29) - Coffee with Digital Trailblazers

    1h 1m
  7. Talent Crunch: Developing Level-1 Expertise in the GenAI Era

    JAN 23

    Talent Crunch: Developing Level-1 Expertise in the GenAI Era

    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Kevin Wallis-Eade Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Heather May Derrick Butts Summary The episode focused on the impact of AI on Level 1 expertise and entry-level roles in organizations. Isaac, the host, shared statistics on declining employment for early career workers and the need for companies to adapt their hiring and training practices. Participants discussed how AI is being used to automate tasks traditionally performed by entry-level employees, raising concerns about the loss of critical skills and knowledge. The group explored strategies for companies to retain and develop Level 1 expertise, including retraining programs, apprenticeships, and a shift in how roles are defined in an AI-driven world. They emphasized the importance of critical thinking, context awareness, and decision-making skills in the new AI landscape. The conversation also touched on the need for organizations to adapt their change management practices and redefine roles to maximize the benefits of AI while minimizing disruptions to the workforce. See the blog post on 4 Ways to Boost Entry-Level Talent in the Gen AI Era StarCIO Research Sources Constellation Research – A Stanford study using ADP payroll data finds a 13% relative decline in employment for early‑career workers CNBC – Postings for entry-level jobs in the U.S. overall have declined about 35% since January 2023 Institution Labs – AI’s impact on graduate jobs ComputerWorld – 77% of early-career and 67% of tenured workers believe AI raises expectations for entry-level roles Chapters (00:00:02) - Talent Crunch and the Impact on Level 1 Expertise(00:04:57) - The Need for Level-One Expertise in AI(00:07:53) - "What is the most common phrase uttered by recent graduates?"(00:10:53) - The Need for More Learning in Software Engineering(00:11:49) - Hiring from AI(00:13:59) - What Should Security Students Know to Get Ready for the Future?(00:16:46) - CIO Network: Process and Operations Skills(00:19:59) - Seamanship: The Need for Subject Matter Experts(00:21:25) - Six Must-Have Skills in the CIO Skills Inventory(00:24:17) - CIO Network: What Skills Do We Need to Protect?(00:26:12) - The Need for Human In the Lead(00:28:57) - CISO Minute: The Need for Human Intelligence(00:31:03) - Coffee With Digital Trailblazers(00:33:19) - Fourth Industrial Revolution: What to Do With AI(00:36:47) - Mind Shift Around AI(00:39:53) - AI Trade Off-Management(00:41:15) - Apprenticeships for the AI Generation(00:43:09) - Change Management: AI Is Just a Tool(00:52:06) - Will IT staff become managers of AIs?(00:56:57) - Will AI Redefine Jobs?(00:59:40) - Coffee With Digital Trailblazers(01:00:29) - Winter Storms Coming to the US

    1h 1m
  8. CIO and CMO: Partnering on AI to Drive Growth

    12/05/2025

    CIO and CMO: Partnering on AI to Drive Growth

    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Adrianna Hosford Elena Putilina Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Derrick Butts Heather May Summary Today’s panel explored AI’s role in driving revenue and growth through the collaboration between CIOs and CMOs, with discussions centered on customer education, data security, and cross-departmental partnerships. Participants shared their experiences and perspectives on AI implementation in marketing and IT, including the use of synthetic audiences, data analytics, and personalization strategies. The group emphasized the importance of forming cross-functional councils, establishing joint KPIs, and addressing security considerations while exploring future opportunities in areas like health tech and synthetic data. Transcript [00:00:00] Speaker A: Foreign. [00:00:05] Speaker B: Welcome to this week’s Coffee with Digital Trailblazers. Welcome back from the Thanksgiving weekend where we took Friday off and give everybody a break to be with family and to do your shopping and just to to veg out and watch some sports, maybe do some reading. And we are back here this week with a super special episode that I’m very excited about. We’ll be talking about the CIO and CMO relationship and more broadly the relationship between IT leaders and digital marketers and the digital trailblazing leaders in those groups. And how do we partner on AI not just to get more efficiencies or improve our workflow. How are we actually driving growth around this? And I think this is a very important episode. Thank you for joining this week. Part of the reason I’ve been excited about this episode is that we’ve been talking and I’ve been doing a lot of writing about how using AI only for productivity improvements, only for employee experiences and only for workflow gets translated to cost savings. Eventually the CFO catches up with that and gets and calls in the cards and says how are we going to actually realize the cost savings? And most of that ends up coming from headcount. And we’ve seen this rodeo before. For those of you who have led digital transformation efforts, you can’t modernize, you can’t transform by just becoming more efficient or just by improving productivity. You need to transform by using technology and now AI to a competitive advantage. And part of that is looking for ways to dri... Chapters (00:00:00) - CIO & CMO: The CIO-CMO Relationship(00:04:06) - CMO vs CIO: How to Partner with AI at Digital(00:07:00) - What Do You See as the Growth Opportunities in Working With Customers(00:10:13) - CIO Network: Growth Opportunities in the AI Era(00:15:31) - Top Executives: Growth Opportunities in AI(00:18:02) - CIO Network: CMO vs CIO(00:20:30) - CIO vs CMO: Shared Growth Mandate(00:22:33) - What is a Growth Mandate?(00:23:31) - CIO Network: CMO Growth Opportunities and CIO Relations(00:26:48) - Immersive Marketing: Synthetic Audience and Sentiment Analysis(00:30:04) - Coffee With Digital Trailblazers(00:31:53) - CIO and CMO Partner on AI to Drive Growth(00:32:47) - CMO Network: Safety & Security Is Everyone's Job(00:35:30) - CIO Network: The Future of Personalization in Marketing(00:36:52) - AI Partnership: Joint KPIs(00:38:28) - CIO vs CMO: Defining a Growth Mandate for(00:40:46) - Holistic IT: Data-centric Approach(00:44:20) - CMO & CIO Network: On AI(00:47:21) - How to Collaborate with AI in the Future(00:49:15) - Last Thoughts on SEO, AEO and Travel(00:52:01) - CIO Network: How to Build Growth Opportunities with CMO(00:52:39) - CMO & CIO Network: The Future of Data & Security(00:54:29) - AI in Healthcare: Partner on Patient Experience(00:57:36) - CIO Network: Health Tech and Patient Experience

    58 min
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Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffee Digital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life. About the Coffee with Digital Trailblazers Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate. Topics that we cover: digital transformation, AI. genAI, AI agents, agile, DevOps, data science, data governance, IT leadership, CIO, CDO, CMO, CHRO

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