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.

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

    12/05/2025

    CIO and CMO: Partnering on AI to Drive Growth

    The panel, led by Isaac Sacolick, featured discussions by industry experts on how AI fosters revenue growth through CIO-CMO collaboration. Key focus areas included customer education, data security, and partnerships. Participants highlighted the need for joint KPIs, cross-functional councils, and explored future opportunities in health tech and synthetic data. 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
  2. AI for Social Good: Insights From Nonprofit Leaders

    11/15/2025

    AI for Social Good: Insights From Nonprofit Leaders

    Isaac Sacolick hosted a "Coffee with Digital Trailblazers" episode focused on AI in nonprofits ahead of Giving Tuesday. Nonprofit leaders shared their experiences and challenges with AI tools aimed at enhancing impact and donor engagement. The discussion emphasized the importance of strategic planning and collaboration in adopting AI for social good. 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

    1 hr
  3. AI Agents at Work: The IT and HR Alliance to Drive Adoption and Value

    11/01/2025

    AI Agents at Work: The IT and HR Alliance to Drive Adoption and Value

    In this episode of Coffee With Digital Trailblazers, participants discuss AI's impact on the workplace amid tech layoffs, emphasizing change management, culture, and empathy in leadership. They explore the balance between automation and human oversight, highlighting collaboration across teams and future discussions on AI's role in social good and mental health. Chapters (00:00:01) - Coffee With Digital Trailblazers(00:00:34) - AI at Work: Digital Transformation for Leaders in the AI Era(00:02:28) - A More efficient Company with AI?(00:04:10) - IT Leadership: AI Announcements(00:09:58) - WSJDLive: The Future of AI Jobs(00:13:11) - How to Build a More AI-Driven Workforce(00:15:21) - AI Agents: Adoption, Collaboration(00:19:50) - On Board Now: The AI Strategy(00:21:41) - Are We Ready for Fully Autonomous AI Agents?(00:26:37) - AI Agents Will Be Autonomous From the Ground Up(00:28:05) - An AI Security Agent: How long will they be autonomous?(00:30:08) - Are You More Secure Than You Think You Are?(00:31:34) - SOC in the Machine Age(00:32:41) - Coffee With Digital Trailblazers(00:35:38) - HR Adoption, Valuing AI, and Change Management(00:37:39) - Do I Need an HR Department?(00:39:00) - CIO Network: Will AI Destroy Your Board?(00:41:40) - 3 Golden Rules for AI in the IT Organization(00:46:00) - In Attentivating AI Adoption(00:49:10) - SOC Analyses: Will AI Agents Replace the SOC Analyst?(00:51:43) - CIO Network: The Need for Innovation Talent(00:53:14) - AI Agents Enlisting Employees(00:54:23) - IT and HR: The AI Agent(00:57:56) - Top Executives: Blue Sky Strategy(01:00:20) - A Day in the Life of AI

    1h 2m
  4. The Co-Creation Mandate: How Partnerships Accelerate Innovation & Talent

    10/24/2025

    The Co-Creation Mandate: How Partnerships Accelerate Innovation & Talent

    In this episode of Coffee With Digital Trailblazers, participants discuss the importance of co-creation in innovation partnerships among companies, startups, and nonprofits. They offer insights on onboarding partners, setting expectations, and managing risks, sharing real-world stories and emphasizing the need for collaboration, creativity, and AI readiness for future talent. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:02:31) - What is the Co-Creation Mandate?(00:04:01) - Meet the CIOs of Star CIO(00:04:59) - What are the Key Differences Between Working With a Partner and Working Alone(00:07:33) - Co-Creation and Continuous Innovation(00:09:23) - Co-Creation vs. Single-Team Innovation(00:11:35) - Co-Creating: The Legal Hurdle(00:14:50) - Martin on Co-Creation(00:16:39) - In the Elevator: Co-Creating(00:17:47) - In the Elevator With Startups(00:18:55) - Is the Robot a Good Fit for Your Company?(00:20:26) - Robot-based manufacturing(00:21:52) - Co-Creation in the AI Industry(00:23:16) - What Do Companies Need To Do To Onboarding a Partner?(00:24:57) - Co-Leadership and Innovation(00:27:26) - Co-creation and the Business Cycle(00:33:35) - Coffee With Digital Trailblazers(00:35:37) - Top Executives: Why we're Accelerating Innovation and Co(00:37:05) - How to Bring New Innovation to the Company(00:39:42) - Co-Creation: Accelerating Innovation & Talent Readiness(00:43:25) - How To Identify the Right Partner to Accelerate Innovation(00:47:08) - How to Choose the Right Knowledge Ecosystem Partners(00:49:47) - Culture fit for innovation partners(00:53:38) - How to Find a Partner for Innovation(00:54:39) - Co-creation and Resilience(00:57:03) - Projects & Collaboration: The New Paradigm(00:58:22) - IT and HR Alliance: How Partners Can Accelerate Innovation

    1h 1m
  5. The Cost of Tribal Knowledge: Losing People Can Bring Ops to a Standstill

    09/27/2025

    The Cost of Tribal Knowledge: Losing People Can Bring Ops to a Standstill

    The discussion revolves around the challenges of knowledge management, particularly in construction and manufacturing settings. Emphasis is placed on tribal knowledge, which risks losing operations continuity when key personnel depart. Participants dialogue on barriers like culture and documentation, and explore leveraging technology and AI to bridge knowledge gaps, ensuring smoother transitions and organizational resilience. Chapters (00:00:01) - Coffee With Digital Trailblazers(00:03:11) - The challenges of knowledge management(00:03:51) - Lean Continuous Improvement in Construction(00:04:51) - Give Feedback, Get Feedback(00:06:14) - What's The Barriers to Knowledge Sharing?(00:12:29) - Organization in the IT Organization(00:13:49) - On Documentation and Process Automation(00:15:14) - Knowledge Management: Is it Too Complex?(00:19:43) - Construction and Manufacturing: The Digital Industrial Applications(00:20:53) - What are we most concerned about when we think about losing tribal knowledge(00:25:15) - On Loss of Skills(00:27:25) - CIO Network: Group Think and Learning(00:31:17) - Tribal Knowledge(00:32:43) - The Future of AI in the Construction Industry(00:36:12) - The Need for Documentation in the Security Industry(00:42:12) - Machine Learning for Maintenance: The Future of Tech(00:47:44) - Including Tribal Knowledge in the AI Process(00:52:27) - Standard Operating Procedures and Dynamic Work Management(00:54:56) - How to Make Tribal Knowledge Obsolete with Tech and AI(00:57:07) - Common Stream: The Real Cost of Tribal Knowledge(00:59:46) - Applying Quickbase to Construction Workflows

    1h 1m
  6. AI as a Teammate: Crafting Purposeful Digital Workplaces

    08/22/2025

    AI as a Teammate: Crafting Purposeful Digital Workplaces

    The 139th episode of "Coffee with Digital Trailblazers" featured Stephanie Sylvester discussing AI's role as a teammate in digital workplaces. The discussion included AI implementation strategies, organizational readiness, and security considerations, emphasizing productivity enhancement and maintaining human expertise. Future meetings aim to further explore AI's impact on digital transformation. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:02:36) - AI as a Co-Workmate(00:05:29) - Coffee Hour: AI is a Social Construct(00:09:25) - Workplace Conflict in the Age of AI(00:11:53) - Change Management in the Age of AI(00:13:02) - Training and Onboarding AI Agents(00:16:53) - Can AI Agents Help with Digital Transformation?(00:23:04) - Is AI Just a Component of Digital Transformation?(00:24:06) - The Future of Customer Service Agents(00:25:39) - Onboarding an Outsourcing Team(00:27:09) - Onboarding and Integrating an Outsourcing Team with AI(00:31:05) - How To Train Your AI Agents(00:36:32) - Change Management in an AI World(00:41:12) - Find Your AI Buddy(00:42:55) - Coffee With Digital Trailblazers(00:44:04) - How to Restore Dignity to Work with an AI Buddy(00:52:24) - I Think AI Is Impossible(00:54:27) - AI Agents and the Manufacturing Industry(00:56:38) - A Sense of Purpose in Crafting Purposeful Digital workplaces(00:58:41) - Agents as Social Buddies(00:59:50) - Coffee With Digital Trailblazers

    1h 1m
  7. From Digital Leader to Frontier Firm: AI and Governance Strategies

    07/18/2025

    From Digital Leader to Frontier Firm: AI and Governance Strategies

    Participants Isaac Sacolick Joanne Friedman Heather May Joseph Puglisi Martin Davis Derrick Butts John Patrick Luethe Liz Martinez Niraj Tenary Episode Summary This week’s episode of “Coffee with Digital Trailblazers” focused on the concept of “frontier firms” – organizations that are embracing AI and agents to transform their operations. Key points include: Effective AI governance requires a holistic approach that aligns strategy, operations, and data/security management, rather than just policy-based controls. Frontier firms are blending machine intelligence with human judgment, creating AI-operated but human-led systems. Adopting AI and agents requires careful governance and collaboration across IT, security, legal, and business teams to manage risks and ensure reliable, secure operations. Leading organizations are using AI agents for tasks like software development, compliance, and customer service – with humans maintaining oversight and control. Transcript Isaac Sacolick: Greetings everyone. Welcome to this week’s Coffee with Digital Trailblazers. I’m just going to give this a few seconds to get a bunch of people here and we’ll get started with a very interesting topic with a very interesting guest and just sit tight. This is our hundred, is that right? Hundred 35th episode. Holy cow. Time flies by and I met a whole bunch of new people this week that I’m excited to have on the program and be a part of our community of Digital Trailblazers. If you are here, please do say hello in the common stream and I look forward to this conversation. We’re you going to be talking about from digital leaders to Front Frontier Firm? And I’m going to let our special guest, Neraj Dani, who’s the CEO of net woven, tell us a little bit about that when we get started. We are just waiting for getting a few more people here and then we’ll start with our conversations today. Hello Gloria. Welcome. Got Derek on here on the common stream. We’ve got Neraj. Who else is here today? Everybody do say hello. I want this to be an open conversation. Hello Dennis. Thank you for joining. You’re all welcome to comment. I will call out some of the comments that I think are useful. We might put some of our comments into the actual whiteboard as we start creating it. Hello Jay. Jay is a good friend, StarCIO member, an X Microsoft. I’m just going to say an ex Microsoft TA copilot experts. Great to see you. Hello Michael. Thank you for joining from Atlanta. Michael, I think you know this, I’ll be speaking on Atlanta. The new date is September 10th. This is an event at the Microsoft Center that net woven is sponsoring and I am very excited to be there. So Michael, if you don’t have the access link to get to that, do let me know. I’ll make sure you get on the list to be able to come see that program on AI governance in about a little bit over a month. Folks, thanks for joining this week’s conversation from... Chapters (00:00:00) - Coffee With Digital Trailblazers(00:01:20) - Comments on Microsoft's AI Governance(00:02:30) - Beyond Digital Leader to Frontier Firm: AI Governance(00:03:57) - What is the Frontier Firm in the AI Era?(00:07:09) - The Need to Be On The Frontier of AI(00:08:41) - WSJD Live: AI's Technology Inflection(00:10:17) - Agents and the Internet of Agents(00:11:42) - What Is a Frontier Firm and Are They Secure?(00:13:43) - What are the table stakes for being a frontier firm?(00:17:27) - What is a Frontier Firm?(00:19:24) - Human Agents: The Future of Work(00:20:33) - Neeraj Gupta on Human Agent Teams(00:23:13) - Vibe Code and How It Affects Your Business(00:24:49) - Vitya on Agents and Workflows(00:27:12) - Human Agent Teams and their Business Value(00:28:57) - What Does a Human Agent Team Look Like in Security?(00:31:23) - What is a Human in the Loop(00:34:57) - Coffee With Digital Trailblazers(00:35:46) - All the Agents in the Cloud(00:37:49) - Microsoft CIO on Innovation in Security(00:39:35) - Will IT Companies Crawl, Walk, Run?(00:41:39) - Microsoft, Google on AI Governance(00:44:45) - How to Govern AI with Cybersecurity?(00:49:46) - Department of No vs the Department of No. 1 in AI Govern(00:52:28) - Microsoft on AI and Governance(00:53:24) - Data Security and Protection for the AI Era(00:58:31) - A New Era of AI(00:59:42) - Coffee With Digital Trailblazers

    1h 2m
  8. AI Era Transformation: Is AI the End of IT (as we know it)

    06/06/2025

    AI Era Transformation: Is AI the End of IT (as we know it)

    Participants Isaac Sacolick Joanne Friedman Heather May Joseph Puglisi Martin Davis John Patrick Luethe Episode Summary AI is increasingly automating and transforming traditional IT functions like software development, testing, operations, and infrastructure management. This raises questions about the future of IT jobs and departments. However, the consensus is that IT roles will evolve rather than disappear completely. IT professionals will need to focus more on strategic business alignment, understanding user needs, and applying the right tools and technologies to drive value. New roles will emerge around areas like AI governance, data strategy, and optimizing AI and cloud usage. IT professionals will need to develop a mix of technical, business, and leadership skills to succeed. Organizations will need to rethink their IT operating models and talent strategies to adapt to the AI era. This includes consolidating roles, developing multi-skilled employees, and finding the right balance between human and AI capabilities. Overall, the IT industry is undergoing significant transformation, but IT professionals who can evolve their skills and roles will continue to be valuable assets to their organizations. Transcript Isaac Sacolick: Greetings everyone. Welcome to this week’s Coffee with Digital Trailblazers. Great to have you here this week I’m going to give my usual two or three minutes for everybody to join. We’ve got quite a bit of signup for this one, so clearly people are interested in the future IT and what AI is or will not do to it. I’m not surprised that we will want to hear how leadership is going to change, how the different functions in IT is going to change how you’re going to change your career. So very excited to see this. Hello, Steve. Hi Chris. Chris is my supporter of the week. I want to just thank Chris for just being such an outstanding partner. I think I announced a few times I was scheduled to do a keynote out in Atlanta next week on AI governance and he is helping me reschedule that because of things that I’m going through personally. So I just want to thank Chris for just being such a strong friend and supporter and go check out net woven and give a date here. Chris. I think we’re doing it September 10th as our rescheduled date for those of you in the Atlanta area. We’ll be doing an AI governance summit around then and I’m really excited for it. Of course, that means I’m going to have to update my deck again because by the time we September rolls around everything we’re talking about AI today, we’ll be completely obsolete or at least different and we’ll have some new things to talk about. We’ll see Martin and Joe, we’ll see if that continues on that way. Hello Jay, welcome for joining and our conversation this week. AI era transformation is the ai, the end of it as we know it. There are some who might suggest it is the end of it every four to six years there’s some maverick in Harvard Business Review who comes up with some kind of article suggesting that it has done and then of course we’re like, well, not so fast. Chapters (00:00:00) - Coffee With Digital Trailblazers(00:02:02) - Is IT Ready for the AI Era?(00:04:26) - CIO Network: The AI Code Challenge(00:05:53) - How Is AI Shaping the IT Landscape? DevOps,(00:11:49) - CIO Network: IT becoming a Business Unit(00:14:21) - Are Apps the Future for Agents?(00:15:30) - What is an AI Agent?(00:18:15) - CIO Network: AI and the CIO's Role(00:20:26) - IT Proposals: The New Requests(00:23:27) - IT Organization: The difference between generative and agentic AI(00:27:02) - What are the New Roles that AI Will Enable?(00:28:10) - Coffee With Digital Trailblazers(00:29:30) - How will ITSM cloud infrastructure and end user computing evolve in the(00:30:39) - What's the Next 2 years of IT transformation?(00:33:07) - CIO Network: Is IT Operations Capable with AI?(00:35:03) - IT Operations: Will DevOps Completely Disappear?(00:37:48) - IT Operations Skills in the AI Era(00:44:16) - Third Area of IT Continuous Improvement(00:46:10) - Quantum Computing: The MSPs(00:47:36) - CIO Network: CIOs need to recalibrate their(00:49:52) - New Jobs and the Business Unit(00:51:09) - Wearing Many Hats: CIOs' Hiring Strategy(00:54:15) - How to Refitting the IT Organization in the AI Era(00:55:47) - What are you doing as a CIO to prepare your org for(00:58:46) - Is AI the End of IT as We Know It?(01:01:14) - Coffee With Digital Trailblazers

    1h 2m
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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.

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