Why AI Rollouts Fail After Deployment and How to Keep Them Alive w/ Katrina McCullough

💡 Deploying AI is the easy part. Getting people to trust it, use it, and build it into how they actually work — that is where most rollouts fail.

In this episode, Brian speaks with Katrina McCullough, founder of McCullough Management, whose work spans ERP consolidations, digital transformation, and PMO leadership across large organizations including school districts and procurement-heavy enterprises. Katrina brings a people-first philosophy to AI implementation: systems are built for people, and adoption follows when the workflow supports real users.

She shares how she uses AI to turn messy data exports into executive-ready dashboards, synthesize meeting transcripts into one-page summaries, build RAID logs and communication plans faster, and rank resumes for complex staffing workflows. Her core argument is that AI earns trust not through novelty but through the quality of the work it produces — better emails, clearer reports, faster decisions.

✨ In This Episode, You'll Learn

• Why AI rollout success depends on what happens after deployment
• How to build trust in AI through execution, not kickoff meetings
• Why visibility into project trajectory matters more than status updates
• How to turn raw data exports into actionable dashboards using AI
• Where AI saves the most time in project and change management
• How AI helps tailor the same information for different audiences
• Why good AI strategy starts with your biggest pain points, not the most impressive tools
• How to reduce delayed decisions with better data and communication

👤 Connect with Katrina McCullough

💼 LinkedIn: Search Katrina McCullough

🌐 McCullough Management: Search McCullough Management

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🎙️ Welcome to AI with Bry – Learn. Leverage. Lead.

You’re listening to the show that helps founders, operators, and marketers unlock the full potential of AI in real business settings. Hosted by Bry Dennstedt — Fractional CTO at TechCXO and founding technologist behind MDLIVE’s early growth — this podcast gives you insider access to how AI is transforming startups, SMBs, and scaling companies in real time.

Each episode dives into practical AI use cases, expert interviews, powerful prompt ideas, automation workflows, and the latest in generative AI, agentic systems, multimodal tools, and more.

Whether you’re looking to:

✅ Deploy AI tools like ChatGPT, Claude, or Gemini

✅ Build agent workflows to run your marketing or ops

✅ Use AI to generate video, audio, or stunning visuals

✅ Save hours with prompt engineering and automation

✅ Or just scale smarter with real, proven strategies…

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