Ashley Gross has been at the forefront of AI long before ChatGPT made headlines and has spent years helping enterprise and mid-market companies implement AI in ways that drive real business impact. Her expertise lies in aligning leadership and teams, ensuring AI isn’t just a buzzword but a strategic tool that delivers measurable results.

Beyond consulting, Ashley speaks, teaches, offers courses, and leads executive workshops, breaking down AI into practical, actionable strategies that help companies stay ahead. She is one of the top voice in AI on linkedin and I recommend you give her a follow.

In this conversation, Ashley breaks down how to identify the right use cases for AI, where companies waste time and money with misaligned tools, and how to architect a sustainable AI roadmap that includes strategy, enablement, and internal builds. She shares her philosophy on why change management is the most critical skill in AI adoption, and how to get stakeholder buy-in across departments—even in risk-averse environments.

We also dive into her favorite foundational automations and life hacks. Please enjoy this conversation with Ashley Gross.

TOOLS & PLATFORMS MENTIONED

• Generalist LLMs – ChatGPT, Claude, Gemini, Copilot, Perplexity
• Automation & Agent Platforms – Make, N8N, Blue Prism
• Note-taking & Sentiment Tools – Read AI
• Communication Optimization – Prompt libraries for stakeholder management
• Enterprise Builds – Custom AI tools connected to tech stacks via Slack/Teams with Microsoft Cognitive Search

ASHLEY’S COURSES

• Optimizing ChatGPT (launching May 13)

→ Get it for $50 (first 500 signups): theashleygross.com

• Also available:

→ Automation & agentic workflow courses

→ Courses on building internal AI solutions

→ Strategic AI implementation playbooks

• LinkedIn: https://www.linkedin.com/in/theashleygross/
• Website: aiworkforcealliance.com/
• X (Tweeter): X.com/theashleygross
• Instagram: instagram.com/theashleygross