About

“Gray's ability to simplify and clarify complex situations is incredible. He is able to quickly crystalize ideas that may have been swimming in my head for hours or days, bringing a level of clarity that is immensely valuable.”

I partner with organizations to develop their leaders.

With two decades of success on the product side of premier tech companies—including Amazon, Expedia, Groupon, and Workiva—building and leading teams that have driven hundreds of millions in revenue growth, I partner with organizations to develop leaders to their fullest potential to achieve exceptional business outcomes.

During my 20 years as a leader and executive at some of the world’s most innovative tech companies, I consistently built and led teams to the highest levels of performance, frequently disrupting the status quo in order to seize opportunities and deliver outsized business outcomes. My teams were consistently recognized for their operational excellence, their ability to drive innovation, and for revenue outcomes in the hundreds of millions of dollars. I have led scaleups, team turnarounds, and multiple zero-to-one business launches.

As a leader at Amazon in the early 2000s, I learned from the very best what it takes to create a culture of innovation and excellence. I applied this at Groupon where his teams were faced with the need to urgently re-invent the company from email to web to mobile over a few short years. At Workiva, my teams led the integration of cutting-edge Generative AI technologies into their products, delivering an unprecedented 98% customer retention rate while maintaining high employee engagement with a Great Place to Work® satisfaction score of 99%.

In 2023, I left my final operational role in order to found Black Diamond Coaching, an executive leadership development firm. Black Diamond’s client companies include Fortune 50-2000 companies, private companies, and startups across industries and verticals. In addition to being a Certified Executive Coach® from the Inpowered Coaching Institute and a Co-Active Trained Coach® from the Co-Active Training Institute, I hold a degree in Computer Science and a minor in Human Psychology from Cornell University.

My services include one-on-one executive coaching, operational culture transformation, and leadership and team development. I also specialize in leading through the age of AI and driving innovation for business outcomes.

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  • “Gray is one of the most caring people I’ve ever come across in my career or life.”

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  • “If you want to change your career, drive amazing results, or get unstuck, there is no one better to work with than Gray.”

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  • “Having Gray as my thought partner and my coach would take whatever I was doing and accelerate it 5x.”

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  • “Gray knows his sh*t incredibly well. He shares his insights unflinchingly and with a directness that somehow leaves you feeling supported and more at peace.”

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  • "Gray is really good at reflecting people's behaviors on them in a way that feels safe. I never felt attacked or defensive. Gray would just say, 'This is what you're doing,' and I would be like, 'Oh f*ck, that's what I'm doing.’”

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  • “Gray talked to me so much about not caring about certain things, and that was huge. Letting things go and letting fires burn; and instead focusing on what matters the most.”

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  • "One of the most powerful things Gray worked on with me was controlling my reactions. He taught me to take a moment and think through how I wanted to proceed instead of responding with a stream of consciousness."

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  • "Gray taught me how to carry myself with executive presence.”

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  • “Working with Gray put me on a path to being a rising star of the company.”

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  • “Gray isn’t ego driven and he isn’t a showboat. Until you work directly with him you may not realize just how incredibly smart he is; he is truly brilliant.”

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  • "If you’re looking for a coach who will challenge your thinking, shift your perspective, and help you move forward with confidence, I highly recommend Gray."

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