Episodes

  • Developing Your Personal Brand: Best Practices From Thought Leaders

    Developing Your Personal Brand: Best Practices From Thought Leaders
    Apr 10 2026
    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
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    1 hr
  • Redefining Data Governance: Is the Data Owner Role Obsolete in the AI Era?

    Redefining Data Governance: Is the Data Owner Role Obsolete in the AI Era?
    Apr 3 2026
    The meeting, hosted by Isaac Sacolick, focused on redefining data ownership in the AI era. Panelists discussed evolving responsibilities, emphasizing context-specific governance, AI readiness, and accountability. They highlighted key challenges, including managing complex data contexts and the need for data owners to possess AI literacy, distinguishing between generative and agentic AI approaches. Chapters
    • (00:00:00) - Coffee With Digital Trailblazers
    • (00:00:32) - Is the Data Owner Role Obsolete in the AI Era?
    • (00:03:22) - The Data Owner's Role in the AI Era
    • (00:05:47) - Interview
    • (00:07:02) - The role of a data owner in the AI era
    • (00:08:11) - The New Data Ownership: What's the Role of the Traditional
    • (00:13:51) - Data Owners and Their Expanded Role
    • (00:16:21) - The Role of Data Owners in the AI Era
    • (00:18:37) - On Data Ownership in the Agentix Era
    • (00:24:00) - data owners: The role of AI agents in the AI era
    • (00:29:06) - The Need for Context in AI
    • (00:34:09) - Coffee With Digital Trailblazers
    • (00:36:09) - How should data owners express who, when, how to use their
    • (00:40:54) - Data Governance: The Context of AI
    • (00:42:19) - Data ownership and the resilience of the organization
    • (00:44:05) - The CDO's role in AI Governance
    • (00:54:41) - Inventing the Agent in the Digital World
    • (00:56:10) - Data Governance: Agile vs. SAS
    • (00:57:46) - The New Data Owners: Final Thoughts
    • (00:58:50) - Coffee With Digital Trailblazers
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    1 hr and 1 min
  • Managing AI Agents: New Skills, Operating Models, and Tools

    Managing AI Agents: New Skills, Operating Models, and Tools
    Mar 20 2026
    The event hosted by Isaac Sacolick featured discussions on managing AI agents with special guests, referred to as Digital Trailblazers. Insights were shared from studies indicating that 74% of organizations plan to deploy AI agents soon. A focus was on understanding performance management, risk, and the governance surrounding AI technologies, emphasizing the need for structured oversight and accountability. 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
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    1 hr
  • National Entrepreneurship Week: Opportunities for Digital Trailblazers

    National Entrepreneurship Week: Opportunities for Digital Trailblazers
    Feb 20 2026
    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Tyler James Johnson Digital Trailblazers Joanne FriedmanLiz MartinezJoseph PuglisiMartin DavisJohn Patrick LuetheHeather MayDerrick 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. BankTotal 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 CouncilTotal Entrepreneurial Activity in the U.S. is at a historic high: 19% of adults are actively starting or running a new business – GEMGlobally, 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
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    1 hr and 2 mins
  • AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys

    AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys
    Jan 30 2026
    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Roman Dumiak Digital Trailblazers Joanne FriedmanLiz MartinezJoseph PuglisiMartin DavisJohn Patrick LuetheHeather MayDerrick 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
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    1 hr and 1 min
  • Talent Crunch: Developing Level-1 Expertise in the GenAI Era

    Talent Crunch: Developing Level-1 Expertise in the GenAI Era
    Jan 23 2026
    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Kevin Wallis-Eade Digital Trailblazers Joanne FriedmanLiz MartinezJoseph PuglisiMartin DavisJohn Patrick LuetheHeather MayDerrick 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 workersCNBC – Postings for entry-level jobs in the U.S. overall have declined about 35% since January 2023Institution Labs – AI’s impact on graduate jobsComputerWorld – 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
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    1 hr and 1 min
  • CIO and CMO: Partnering on AI to Drive Growth

    CIO and CMO: Partnering on AI to Drive Growth
    Dec 5 2025
    Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Adrianna HosfordElena Putilina Digital Trailblazers Joanne FriedmanLiz MartinezJoseph PuglisiMartin DavisJohn Patrick LuetheDerrick ButtsHeather 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
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    58 mins
  • AI for Social Good: Insights From Nonprofit Leaders

    AI for Social Good: Insights From Nonprofit Leaders
    Nov 14 2025
    Isaac hosted a special episode of “Coffee with Digital Trailblazers” focused on AI in nonprofits ahead of Giving Tuesday. Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests – Non-profit executives Larry Lieberman, CEO of Mouse.orgStephen Rockwell, Chief Innovation Officer of AmplifiTeresa Duran, Technology Advisory Council of Big Brothers Big Sisters of AmericaGlen Ford, Former Director of International Development and Trustee at Aegis TrustDerrick Butts, Board President and co-founder, Prostate Health Matters Digital Trailblazers Joanne FriedmanLiz MartinezJoseph PuglisiMartin DavisJohn Patrick Luethe Summary Featuring a panel of nonprofit leaders discussing their experiences with AI tools to drive impact and reach donors. The episode explored various nonprofit use cases, including education, public benefits access, and health initiatives, with panelists sharing their experiences and challenges in implementing AI solutions. The discussion emphasized the importance of AI adoption in nonprofits, highlighting the need for strategic planning, collaboration with tech companies, and focusing on social impact rather than just efficiency. Transcript [00:00:05] Speaker B: Welcome to this week’s coffee with Digital Trailblazers, our 150th episode. I’m really excited to announce that I’m really excited to have a full house today, our largest speaker panel on this program and we’re talking about something really important to me. I am not an expert around nonprofits, but I have worked in nonprofits and we are heading into the holiday season. Giving Tuesday is coming up right after the Thanksgiving holiday. And in planning November’s episodes, I wanted to have just a special episode just talking about not only AI for social good, but just giving some of our nonprofit leaders the mic to talk about all the special things they’re doing to drive impact with their constituents, how they’re using AI, how they’re using technology to drive their cause, how they’re using AI and technology maybe to become more efficient, to reach a wider donor base and obviously to impact their social causes as well. I have five special guests today an... Chapters (00:00:00) - Coffee With Digital Trailblazers(00:02:42) - AI for Good: Impact on Nonprofits(00:05:02) - Machine Learning in the Classroom(00:07:52) - AI for Good with Stephen Rockwell(00:10:39) - AI Agents in the Nonprofit World(00:13:16) - Interview(00:13:39) - Glenn on AI and Non-profits(00:18:40) - Champions: Stories of Humanity(00:22:53) - CIO Network: Teresa Duran's Charity and AI(00:28:11) - Are Nonprofits Ready for AI?(00:31:40) - How Nonprofits are Using AI(00:36:15) - Coffee With Digital Trailblazers: AI for Social(00:37:24) - AI and Nonprofit Governance(00:40:27) - Steve Jobs on AI and the New Economy(00:41:42) - John and Larry on AI and Nonprofits(00:43:24) - Immigration of AI into Nonprofits(00:48:44) - Nonprofits and the AI revolution(00:50:53) - How to Get Funding for Your Nonprofit with Artificial Intelligence(00:52:26) - Working with a nonprofit in the AI world(00:56:54) - How to Prevent AI From Dehumanizing Nonprofits(00:58:45) - AI for Social Good
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    1 hr