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
- 9/25 – Getting Hired in the AI Era: Stand Out, Signal Judgment, Land the Role
- 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
This Week’s Episode
Last 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
- What’s funded: It’s budget season. The CEO/CIO/CAIO have committed to 200+ AI agents in production by the end of 2027 — agents shipping inside our ERP, HRMS, and CRM, plus proprietary agents. Fifteen months. You get to pitch one incremental funding area. What is it and why?
- What’s protected and where to cut: The CEO wants to plan for a recession in 2027. What’s one area of the budget that you’ll fight to protect, and what’s another area where you’d look to make cuts?
- How funding decisions are made: Now you are the CEO/CIO/CAIO, and you have to decide what gets funded, what’s protected, and what you cut. How do you make those decisions?
Research
Dashboard
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
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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