Coffee with Digital Trailblazers
The Coffee With Digital Trailblazers is a LinkedIn Live Event, and we meet just about every Friday at 11am ET. Every week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate.
We discuss topics for digital transformation leaders, i.e., Digital Trailblazers, who are driving business value from innovation, culture transformation, agile collaboration, and change management across their organizations.
Upcoming Episodes
- 10/2 – Vibe, Buy, or Automate? Deciding How to Build AI Agents
- 10/9 – Change Management: Why AI Adoption Stalls and How to Measure Progress
- 10/16 – AI Infrastructure Debt: Strategies for Capacity, Resiliency, and Modernization
- 10/23 – Finishing Strong: How Digital Leaders Close Out the Year
- 10/30 – AI Agent Strategy: Human Augmentation vs In-The-Middle, vs Agentic?
This Week’s Episode
Speakers
- Host – Isaac Sacolick
- Digital Trailblazers – Derrick Butts, Martin Davis, Joanne Friedman, John Patrick Luethe, Liz Martinez, Heather May, Joseph Puglisi
Discussion
- Traditional automation vs. AI agents. Tokenomics, rules vs. judgment-driven— what other factors help decide when an AI agent is the better solution versus automations, apps, APIs, or other options.
- Custom build, vibe with a model, or buy AI agents: What are the decision criteria around solutioning options, and what are the owner/developer responsibilities when implementing and deploying an AI agent?
- How can organizations avoid AI agents becoming the next sprawl, debt, and legacy—avoiding the issues with millions of spreadsheets, hundreds of SaaS apps, and apps without support models?
Research
Sources
- Spreadsheets (millions/firm) — M365 Princess
- 1,742 apps, ~60% built in-house — IDG, via F5
- ~660–696 SaaS apps — Zylo 2026 SaaS Mgmt Index
- 56% of apps IT-approved — BetterCloud 2026 State of SaaS
- 150,000 agents/Fortune 500 by 2028 — Gartner, via WSJ
About the Coffee With Digital Trailblazers
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Recent Episodes
Watch the full episodes on LinkedIn
- 6/26 – AI Agents for Skeptical Boards: What’s Actually Working in Production
- 7/10 – Reskilling Mid-Career Leaders: What Senior Talent Needs to Stay Relevant
- 7/17 – Does IT Leadership in the AI Era Require an IT Background Anymore?
- 7/24 – FinAI & Managing AI Costs: Innovation, Production, and Lifecycle
- 7/31 – Evaluating Technologies in the AI Era: Value, Risk, Ecosystem Evaluation
- 8/7 – Networking in the AI Era: A Guide for Digital Transformation Leaders
- 8/14 – Beyond Legacy Processes: Engineering the High-Velocity Enterprise
- 8/21 – Shadow AI at Work: Real Risks, Practical Guardrails, Hidden Innovation
- 8/28 – SaaS, Cloud, and AI Contracts: Where Technology Leaders Lose Leverage
- 9/11 – The Hidden Cost of Confident AI: Semantics, Guardrails, and the Context Layer
- 9/18 – Tech Budget 2027: AI Bets to Fund; What IT and Security to Protect
- 9/25 – Getting Hired in the AI Era: Stand Out, Signal Judgment, Land the Role
Four Ways to Listen!
- Join the live event on LinkedIn Fridays at 11am ET
- See the Whiteboards and listen here at the StarCIO Digital Trailblazer Community (episode list below!)
- Subscribe on Apple Podcasts, Amazon Podcasts, and Spotify (selected episodes)
Coffee With Digital Trailblazers – Themes
We cover many topics, but have several recurring themes:
- Accelerating Transformation – Developing force multipliers in digital transformation that accelerate the delivery of multiple business values
- AI Era Transformation – Looking at what AI can deliver in the short and longer-term, and what Digital Trailblazers should be leading to deliver AI impacts
- Shaping Tomorrow – About emerging technologies, their business opportunities, disruptive threats, and how Digital Trailblazers can accelerate innovation
- Culture Transformation – Leadership and disciplines that drive culture change, including agile, design thinking, product management, and change management
- Cultivating Digital Trailblazers – Hiring, retaining, mentoring, and coaching Digital Trailblazers – and also how Digital Trailblazers find opportunities, expand their responsibilities, and plan their careers.
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Recordings: Coffee with Digital Trailblazers
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