AI Heroes & Headaches

Military Precision and Machine Learning with Keith McCormick

From Military Discipline to AI Leadership.
95% of AI pilots stall. Only 5% scale. Keith McCormick knows why.
Before teaching over 1M learners on LinkedIn Learning, Keith served in the military, a foundation of discipline and clarity that he now brings to AI adoption.
In Episode 3 of AI Heroes & Headaches, Keith shares why most organizations don’t fail on technology, they fail on culture.
Highlights you’ll hear:
- Why 95% of AI pilots stall, and what the 5% get right
- Messy data = messy AI (no shortcuts here)
- Culture, governance, and upskilling > hype and tooling

From 1800 Flowers to InstaLILY AI with Amit Shah

What do you actually learn running a $1.8B global brand that helps when you launch a new frontier in AI? That’s the journey of Amit Shah, Founder & CEO of InstaLILY AI and former President of 1-800-Flowers.com. 🌸 In Episode 2 of AI Heroes & Headaches, Amit and I dive into: - How scaling one of the world’s most iconic consumer brands prepared him for AI entrepreneurship - The tension between founder mode and coach mode as leaders navigate transformation - Why personalization is the real unlock, and what it means for the future of AI-powered customer connection Every hero has a headache. In AI, the two always come together.

Chief Test Officer with Muralidhar Krishnaprasad

In AI, the hardest code to crack isn’t the tech. It is leadership.
For our very first AI Heroes & Headaches episode, I couldn’t have asked for a better guest than Muralidhar Krishnaprasad (MK), President & CTO of Salesforce’s Unified Agentforce Platform, one of the most authentic, game-changing leaders I’ve ever worked with.
Three months ago in Hakone, Japan, I needed yen to buy a blessed souvenir. Without hesitation, MK walked hundreds of steps down to an ATM, and back up, with me.
It wasn’t about money. It was about trust, respect, and showing up for people when it counts.
In this episode, MK and I dive into:
Why he's known as the Chief Test Officer by our team.
The principle he brings from his spiritual life into his leadership. (MK and I have been to temples around the world together!)
Why authenticity is a strategic advantage in the AI era.
A recent rabbit hole that MK went down, just for the joy of learning.
The message he wants all leaders to know.
"We’re in the agentic AI era, and that’s what’s going to make the next level of transformation possible.” -MK

AI Heroes & Headaches - Trailer

I’ve seen AI deliver million-dollar breakthroughs and I’ve seen it crash and burn.I’m Vivienne Wei, COO of Salesforce Unified Agentforce Platform. I’m pulling back the curtain on the wins, the flops, and the leadership calls that make or break AI transformation.Each episode, I sit down with executives and builders in the trenches of AI from unicorn founders to Fortune 100 CTOs. They’ll share what worked, what failed, and what they’d never do again.No hype. No doomscrolling. Just the unfiltered playbook for leading—and surviving—in the age of AI.Your next AI hero story or headache might be right here.