StarCIO Digital Trailblazer Community
Coffee With Digital Trailblazers
Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffeeDigital 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 TrailblazersEvery 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, d...
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StarCIO Digital Trailblazer Community
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Latest episode
Jun 26, 2026
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Episodes
AI Agents for Skeptical Boards: What's Actually Working in Production 26.06.2026 1:01:24
In the 178th episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, a panel discussed board perspectives on AI investments. They highlighted challenges like FOMO versus cost concerns, the shift from replacement to augmentation of human roles, and emphasized governance and realistic expectations amid increasing AI budgets despite ROI struggles. Chapters (00:00:01) - Coffee With Digi...
From Idea to Impact: Shrinking Innovation Cycles With AI 29.05.2026 1:01:58
Isaac Sacolick hosted a discussion on innovation in the AI era. Key insights highlighted the convergence of roles, efficiency of smaller DevOps teams, and the transformative impact of AI coding tools. Despite advancements, challenges in governance and quality assurance in production remain significant, necessitating careful management and strategic oversight. Chapters (00:00:01) - Coffee With Digi...
Mental Health in the AI Era: Easing Fears About the Future of Work 08.05.2026 1:00:26
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. Chapter...
AI Coding Competencies: Hype, Realities, and the Future 17.04.2026 1:03:46
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. Ch...
Developing Your Personal Brand: Best Practices From Thought Leaders 10.04.2026 1:00:15
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 Digi...
Managing AI Agents: New Skills, Operating Models, and Tools 20.03.2026 1:00:22
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 stron...
National Entrepreneurship Week: Opportunities for Digital Trailblazers 20.02.2026 1:02:13
Participants Hosted by Isaac Sacolick , CEO of StarCIO Special Guests Tyler James Johnson Digital Trailblazers J oanne 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 entrepreneur...
AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys 30.01.2026 1:01:15
Participants Hosted by Isaac Sacolick , CEO of StarCIO Special Guests Roman Dumiak Digital Trailblazers J oanne 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 dis...
Talent Crunch: Developing Level-1 Expertise in the GenAI Era 23.01.2026 1:00:51
Participants Hosted by Isaac Sacolick , CEO of StarCIO Special Guests Kevin Wallis-Eade Digital Trailblazers J oanne 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 wo...
CIO and CMO: Partnering on AI to Drive Growth 05.12.2025 58:23
Participants Hosted by Isaac Sacolick , CEO of StarCIO Special Guests Adrianna Hosford Elena Putilina Digital Trailblazers J oanne 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...
AI for Social Good: Insights From Nonprofit Leaders 14.11.2025 1:00:28
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.org Stephen Rockwell , Chief Innovation Officer of Amplifi Teresa Duran , Technology Advisory Council of Big Brothers Big Sisters of America Glen Ford ,...
AI Agents at Work: The IT and HR Alliance to Drive Adoption and Value 31.10.2025 1:02:11
In this episode of Coffee With Digital Trailblazers, the group takes a candid look at how AI adoption is reshaping the workplace—and what it means for people caught in the middle of change. Participants Isaac Sacolick J oanne Friedman Liz Martinez Derrick Butts Joseph Puglisi Martin Davis John Patrick Luethe Summary The conversation starts with HR challenges and the ongoing wave of tech layoffs, a...
The Co-Creation Mandate: How Partnerships Accelerate Innovation & Talent 24.10.2025 1:00:38
In this episode of Coffee With Digital Trailblazers, we dive into the art of co-creation and what it really takes to build strong innovation partnerships. Participants Isaac Sacolick Juanita Olguin Jay Cohen Joanne Friedman Heather May Joseph Puglisi Martin Davis John Patrick Luethe Summary Our guests share honest insights on how companies, startups, and nonprofits can work together to drive progr...
The Cost of Tribal Knowledge: Losing People Can Bring Ops to a Standstill 27.09.2025 1:01:01
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 a...
AI as a Teammate: Crafting Purposeful Digital Workplaces 22.08.2025 1:01:14
Participants Isaac Sacolick Stephanie Sylvestre Joanne Friedman Heather May Joseph Puglisi Martin Davis Derrick Butts John Patrick Luethe Liz Martinez Summary The 139th episode of “Coffee with Digital Trailblazers” focused on the AI teammate role in digital workplaces, featuring Stephanie Sylvester from Avatar Buddy as a special guest to discuss AI implementation and integration strategies. The di...
From Digital Leader to Frontier Firm: AI and Governance Strategies 18.07.2025 1:01:47
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 holi...
AI Era Transformation: Is AI the End of IT (as we know it) 06.06.2025 1:01:50
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 tha...
The Silent Drag on Productivity: Navigating Digital Sprawl 30.05.2025 1:01:33
Participants Isaac Sacolick Christian Potts Joanne Friedman Heather May Joseph Puglisi Martin Davis Derrick Butts John Patrick Luethe Liz Martinez Episode Summary This session discusses the “silent drag on productivity” caused by digital sprawl and the proliferation of SaaS applications in organizations. Key points include: Companies of all sizes are struggling with having too many disconnected to...
Unplugging Experiments, Products, and Businesses That Aren’t Working 04.04.2025 1:00:30
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Building Smarter Organizations: Transforming to Intelligent Operations 21.03.2025 1:01:26
10 Memorable Insights Matthew Frye : “Intelligent operations today is really speaking to visibility and control across the field and back to the office… automating frontline data collection, connecting data and workflows and dashboards to decision makers, and really reducing those manual handoffs that can cause problems.” Joanne Friedman, PhD : “Operational intelligence is kind of table stakes the...
SMB Transformation: How Smaller, Faster, Safer Wins Against Big and Slow 21.02.2025 58:53
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Demystifying Quantum Computing: What Digital Leaders Need to Know 24.01.2025 1:02:20
Summary The team discussed the potential and challenges of quantum computing, with a focus on its applications in various industries and its potential to revolutionize fields like cryptography, optimization, and drug discovery. They also explored the process of adopting new technology, the importance of educating oneself on quantum computing, and the need for C-suite buy-in. The conversation ended...
AI Era Transformation: Gen AI + Design Thinking + Creative Problem Solving 13.12.2024 1:01:57
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Accelerate Transformation: Why AI is Boring in 2025 22.11.2024 1:01:13
About this episode This episode of the Coffee With Digital Trailblazers was sponsored by Appian . Speakers Isaac Sacolick – President of StarCIO. Bestselling author. 1,000+ articles on StarCIO, CIO.com, and InfoWorld. Keynote speaker. CIO and Digital Transformation influencer. Thinkers360 top IT, DevOps, and Agile Leader. Mike Beckley – CTO and founder of Appian Joanne Friedman – CEO/Principal of...
AI Era Transformation: The Future of Work with AI Agents 11.10.2024 1:00:38
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