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
- 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
- 9/4 – No Session – Happy Labor Day
This Week’s Episode

Speakers
- Host – Isaac Sacolick
- Guest speaker – Daniel Meyer, CTO of Camunda
- Digital Trailblazers – Derrick Butts, Martin Davis, Joanne Friedman, John Patrick Luethe, Liz Martinez, Heather May, Joseph Puglisi, Elena Putilina
Discussion
- How are most enterprise business processes “legacy,” and when should leaders add AI to an existing process versus re-engineer an AI-driven process?
- What are high velocity enterprises doing differently in the AI era around governance, improving agent accuracy, developing trust in AI, and recognizing AI’s boundaries?
- What does “the orchestrated enterprise” look like in 3 years?
Research
Whiteboard

About the Coffee With Digital Trailblazers

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Recent Episodes
Watch the full episodes on LinkedIn
- 4/3 – Redefining Data Governance: Is the Data Owner Role Obsolete in the AI Era?
- 4/10 – Developing Your Personal Brand: Best Practices From Thought Leaders
- 4/17 – AI Coding Competencies: Hype, Realities, and the Future
- 4/24 – Tomorrow’s Workforce: Apprentice Pathways for the AI-Driven Organization
- 5/1 – AI POCs that Matter: Selecting, Pivoting, Delivering Value
- 5/8 – Mental Health in the AI Era: Easing Fears About the Future of Work
- 5/15 – Global Teams, Cultural Diversity, and Building AI Products for Everyone
- 5/29 – From Idea to Impact: Shrinking Innovation Cycles With AI
- 6/5 – Growth Hacks in the AI Era: What’s Actually Working Now
- 6/12 – From POC to Production: The Scaling Decisions That Make or Break AI Value
- 6/19 – Advice for the College Class of 2026: Finding Jobs and Meaning in the AI Era
- 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
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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