Host Justin Starbird recently welcomed longtime friend, mentor, and serial innovator Ken Gray to the Tagline Podcast for a conversation spanning decades of experience, lessons from both startups and legacy businesses, and the power of curiosity-driven leadership.
Ken officially retired from a successful career at Caterpillar nearly a decade ago, but he shows no signs of slowing down. In fact, he might be busier than ever mentoring founders, advising startups, and staying at the forefront of B2B innovation. As Justin noted, “You might be busier today than when you were at Cat!”
So what drives Ken’s relentless pursuit of what’s next?
Ken attributes his continued relevance to one deceptively simple strategy: start.
“You don't stand back and analyze it and fret… just start,” he says. “Pick up a tool, experiment with it. See where it leads you.”
He applies this same principle to artificial intelligence and machine learning. Despite being asked to teach others about AI, Ken humbly resists calling himself an expert.
“If I said I was an expert, I’d either be fooling you or fooling me,” he said. “It’s changing so rapidly. You can’t learn AI from the outside, you have to get your hands dirty.”
Whether experimenting with Canva or testing AI-powered site monitoring tools, Ken's approach to technology is driven by curiosity, not ego. It's why he considers himself not a decision-maker, but a “curator of experiments.”
While tech evolves, one thing hasn’t changed in Ken’s view: relationships still drive business.
“Great salespeople succeed because of long-term, trusting relationships. In B2B, that’s everything.”
Ken shared a story from his Caterpillar days about the top salesperson in Europe, someone who sold based on trust, not hype. When a new machine was released, he told Ken: “Call me when you’d be comfortable selling this to your brother.” Once Ken gave the green light, the salesman sold five million-dollar machines ... in the first month!
This deep belief in trust and human connection also influences how Ken mentors startups.
“Startups often chase the next shiny object or quick return. I help them stay focused on the long game, what customers need, not what investors want to hear.”
Storytelling isn’t optional in emerging industries and new technologies, especially in legacy sectors like construction and mining. It’s essential.
Startups like Dig Robotics, where Ken now focuses much of his energy, lack the name recognition of OEM giants like Caterpillar, Komatsu, or Hitachi. Their value needs to be communicated clearly, authentically, and often.
“It’s not about the technology. It’s about solving a burning problem customers have. That’s where the story starts.”
Ken outlines five pillars that guide how he evaluates and tells these stories:
Only after proving value across these categories can a young company earn trust, and eventually, market share.
One of the most exciting projects Ken is involved in today is Dig Robotics, a startup solving one of construction’s oldest challenges: inconsistency in operator performance.
“The difference between a good and poor operator can be a factor of three in productivity,” Ken shared.
Dig’s solution? Use computer vision and AI to monitor operator activity in real time, compare it to ideal performance, and coach the operator toward better outcomes, move by move, machine by machine.
“We're not trying to replace operators. We’re giving them superpowers.”
While Dig isn’t available to the public just yet, it’s in the final stages of testing in massive Israeli quarries. Ken anticipates a U.S. return in early to mid-2026, following refinements and field learnings. And as of the podcast recording, Dig had just received a generous acquisition offer that would give the team financial runway and autonomy to complete their vision.
While some might think a successful exit is a cue to slow down, Ken sees it differently. He plans to stay fully engaged with Dig and possibly, finally finish that book he’s been writing.
“It started as a story about me,” he said. “But it became a story about the people who helped me. Teachers, mentors… the ones who helped me clear the hurdles I faced, especially being profoundly visually impaired.”
Ken’s story, whether told in a podcast, a boardroom, or a future book, is ultimately one of resilience, humility, and a passion for solving hard problems with good people.
As Justin said in closing:
“When you combine great salespeople and great marketing, you supercharge a business. And when you add someone like Ken Gray into the mix, you get something truly remarkable.”
🎧 Listen to the full TAGLine episode here: