HeyJaredCoffee With Digital Trailblazers
Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week.
- Indexed episodes, last 90 days
- 10
- Latest publication
- Sep 28, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 13, 2026
Latest episodes
Getting Hired in the AI Era: Stand Out, Signal Judgment, Land the Role (opens the original)
Read excerpt
Isaac led a discussion focusing on strategies for job seekers in the AI era, highlighting the importance of standing out, signaling judgment, and landing roles. Panelists emphasized showcasing AI expertise, adaptability for C-level positions, and the significance of cultural fit. Insights included the value of self-assessment and problem-solving skills.
Tech Budget 2027: What AI Bets to Fund + IT/Security to Protect (opens the original)
Read excerpt
We focused on technology budget planning for 2027, particularly AI funding strategies. Host Isaac Sacolick led a discussion with panelists on prioritizing AI initiatives, emphasizing strategic clarity and measurable outcomes, while addressing budget protection and identifying areas for potential cuts. Key frameworks were also presented.
The Hidden Cost of Confident AI: Semantics, Guardrails, and the Context Layer (opens the original)
Read excerpt
The discussion led by Isaac Sacolick focused on AI challenges, particularly the "hallucination tax," emphasized by Felix Van de Maele, CEO of Collibra. Contributors highlighted the importance of governance, context engineering, and policy to mitigate AI failures and improve trust. Future topics included AI existential risks and economics.
SaaS, Cloud, and AI Contracts: Where Technology Leaders Lose Leverage (opens the original)
Read excerpt
The 186th episode of Coffee with Digital Trailblazers focused on negotiation tactics for SaaS contracts. Key topics included competitive bidding, avoiding auto-renewals, and ensuring data ownership. Martin Davis presented a checklist of 88 clauses, while participants emphasized the importance of thorough reviews and understanding data rights, especially for AI models.
Shadow AI at Work: Real Risks, Practical Guardrails, Hidden Innovation (opens the original)
Read excerpt
The real risks and practical guardrails around shadow AI, which goes beyond traditional shadow IT with new risks including data leakage, agentic AI poor decisions, and potential legal compliance issues.
Publishing over time
Last 90 days. Choose a month to open its work.
Recurring subjects
Named in the text we hold. One piece can cover several.
Not enough subject data for this period yet.
Audience
No verified audience measurement yet.
About this data
Counts cover the work we have indexed. Tone needs enough text and a confident classification. Excerpts and episode notes are not full articles or transcripts.
Identity or attribution wrong? Suggest a correction.