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
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
- Stand out: What’s the one signal that gets a candidate noticed now – with ATS, recruiters, and hiring leaders – that job hunters, casual lookers, and those preparing for their next role should zero-in on?
- Signal judgment: Pick a skill: (i) What does a qualified result look like on a resume, and (ii) how does someone signal mastery if they’ve learned it but haven’t done it on the job?
- Land the role: What differentiates finishing 2nd/3rd vs. winning the role? What advice do you have for job seekers who fall short in the final interview?
Research
Sources
- Robert Half — Tech roles in highest demand
- Second Talent — Tech job market trends 2026
- Robert Half — Tech & IT hiring outlook
- CIO.com — CIO hiring to heat up in 2026
- deWinter Group — High-demand AI roles 2026
- FutureProofing.dev — AI engineer demand 2026
- TechTarget — Tech job market statistics
- Taplow Group — AI in executive search
- TenHats — Tech job market statistics
- StationX — Cybersecurity job market
- HeroHunt — Fastest-growing AI roles 2026
- Leon Consulting — Cybersecurity salary 2026
- Robert Half — Marketing roles in demand
- Addison Group — Digital marketing hiring
- Taligence — U.S. Marketing Jobs Report Q1 2026
- MarketPro — Hiring the AI-era CMO
- KraftCV – AI Resumes 2026
- Careerscape – Job Search Strategies 2026
- ResumeVera – AI Layoffs 2026
- RecruitBPM – ATS Optimized Resume 2026
- ExpressPros – Skill Exaggeration
- Next One Staffing – Top In-Demand Transferable Skills 2026
- Hyring – Final Round Interview
- Final Round AI – Interview Prep
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
- 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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