Most companies have an AI experiment. Almost none have an AI strategy.
In this episode, hosts Shiv and Kawal talk with Justin Gray — serial entrepreneur, operator, investor, and founder of Lead MD, one of the most respected marketing and revenue operations consultancies in B2B.
He built it from scratch in 2011, grew it to 64 employees, and exited to private equity—with 50% of that exit value going directly to his team through phantom equity.
Justin breaks down where AI is genuinely moving the needle in GTM—reporting, pipeline evaluation, and operational friction—and where it’s failing.
The core problem: AI will always give you an answer. That doesn’t mean the answer is right. Most orgs are feeding it bad data and trusting the output anyway.
He also covers the central thesis of his book, The Go-To-Market Cheat Code—why partner-led growth outperforms cold outreach and why replacing selling with value creation is the only motion that compounds over time.
The takeaway from this one is simple: double-check your AI output.
