Employee Profile: Senior VP North America Jon Gray - Employee #3

Get to know one of our incredible employees from around the world.

Jon Gray, Senior Vice President, North America
Lives in: Austin, Texas
Joined HomeAway: February 2005

At 30 years old, Jon Gray holds one of the most senior positions at HomeAway. He is responsible for more than half of HomeAway’s revenue, overseeing the company’s operations in North and South America.

But how did Jon land such a high-profile gig at a young age? According to him it's all about hard work, great teachers... and a little bit of luck.  

Jon didn’t always know he wanted to run the American operations of a multi-billion-dollar company.

He grew up in Macdona, a small town on the southwest side of San Antonio, and spent his high school years working random jobs, including working on farms and selling shrimp on the side of the road. He also served as president of his school's chapter of Future Farmers of America, where he eventually became a world-class judge of chicken eggs.

During his freshman year, a high school geometry teacher recognized Jon’s potential for greatness and challenged him to apply himself in all of his classes the same way he did in geometry.  While seemingly insignificant at the time, the challenge his teacher presented to him brought out a part of Jon’s personality that would play a huge role in his career: drive.

Jon and his wife June

Jon and his wife June

Ultimately, Jon accepted the challenge, finishing third in his high school class with a 4.0 GPA. Then he followed his high school sweetheart, June (who would later become his wife) to the University of Texas at Austin.

Jon majored in Government with a specialty in Russian Politics because “it seemed like the path of least resistance,” and finished his undergraduate degree in two years. He was driven more by the challenge of taking on an extreme number of courses at once versus the quest to secure a high GPA.

From there, he set his sights on law school, but in a serendipitous turn of events, he switched his focus to business school after performing better on the GMAT than the LSAT.

Jon enrolled in a 12-month MBA program at Acton, which gave him the opportunity to learn from some of the top venture capitalists in the country. It was here he met two of his mentors, Jeff Serra and Phil Siegel, who instilled in him the importance of being a student of the world and taught him that the first ten years of a career are foremost about learning.

Soon after getting his MBA, Jon began interning for Austin Ventures, a prominent venture capitalist firm, where he was introduced to HomeAway co-founders, Brian Sharples and Carl Shepherd. After helping Brian and Carl complete the investment analysis that supported and directed HomeAway’s initial business strategy, Jon, at 21 years old, was invited to join the company as a full-time market analyst and the third HomeAway employee.

He rose through the ranks quickly, taking on the challenge of each new role with the same tenacity he had during his childhood, often working 80-100 hours per week early in his career.

He is the first to admit that success requires hard work, saying, "There will always be those who are smarter or more efficient than you and you can't control that. But you can control how hard you work." Those who've visited his office may notice a clipping on his desk that says, "Mediocrity is a Sin" - a mantra that Jon has adopted during his time at HomeAway.

However, he also believes one of the most important career considerations is your boss. "I have always been mindful of who I report to and I have learned a tremendous amount from the series of leaders who I have had the privilege of working for."

Jon is truly one-of-a-kind and anyone who knows him will tell you he is one of the most loyal, down-to-earth people you’ll ever meet. He can often be heard quoting lines from movies like "Anchorman" or chatting about the Texas Longhorns.

Outside of work, Jon is a loving husband and recently took on a new challenge - that of fatherhood. He is thrilled to work in the travel industry and believes "traveling is the best thing you can do with your time because it gives you perspective and understanding of the world."

“While Jon has gained incredible experience over the years, he has never lost the ‘we can do that’ attitude he expressed to me when I first met him all those years ago,” says Shepherd.