Jon Gray: Chief Revenue Officer of HomeAway

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Jon Gray serves as HomeAway's Chief Revenue Officer, overseeing delivery of global revenue and management of the business development, sales and regional business teams.

Gray is one of the original HomeAway employees, joining the company in September 2004 before it was officially founded in 2005. During his time with the company he has served as director of global marketing strategy and analysis, director of operations, general manager of, senior director of North American Marketing and, most recently, Senior Vice President of the Americas. He has helped facilitate more than 10 vacation rental site acquisitions. He was also instrumental in launching HomeAway’s marketing strategy, sales and online marketing departments. Prior to HomeAway, Gray worked for Austin Ventures, one of the investment capital firms that has funded HomeAway since its inception. He holds a bachelor’s degree in Government from the University of Texas at Austin and an Acton Master of Business Administration degree in Entrepreneurship from St. Edward’s University.

How did you get into the Tech industry?

HomeAway was my first job in the tech industry – I joined as an intern when I was 22 years old and had recently completed business school. I was introduced to HomeAway through Austin Ventures and joined because HomeAway’s focus on growth through acquisitions aligned with my interest in M&A. As I’ve become more familiar with it, I have grown to truly love both the tech and vacation rental industries.

Tell us about HomeAway. What inspired the idea and what is your vision for the company?

HomeAway was born out of a deep love for staying in vacation homes but a frustrating experience when trying to do so. In the early days, finding and booking a vacation rental online was difficult and time-consuming. With thousands of smaller property management companies and tens of thousands of individual vacation rental owners operating in the space, the vacation rental landscape was incredibly fragmented and highly disorganized. Brian Sharples, HomeAway cofounder and CEO, frequently rented ski and beach homes for family vacations – they loved the experience of staying in a house, but the booking process was a chore. In time, he realized that there was an incredible opportunity to transform the vacation rental industry by consolidating it and making the entire process easier and more secure for travelers. That’s when he decided to found HomeAway, with the help of co-founder Carl Shepherd.

Ten years later, our vision for the company is the same as it’s always been: to make every vacation rental property in the world available to rent in one place – and to make sure that the process is as seamless as booking a hotel.

What strategic partnerships/marketing strategies have you implemented that have attributed to HomeAway's success?

HomeAway’s overarching mission from the beginning has been to make every vacation rental property in the world available in one place. Although we now have more than one million vacation rental listings in 190 countries around the world, there’s still plenty of room for growth. The vacation rental space is a $100 billion industry, and HomeAway customers account for approximately 12% of that.

Traditionally, much of our growth has been driven by acquisitions and strategic investments – we’ve acquired more 23 companies to date. Today we also partner with companies like Expedia and Kayak to distribute online-bookable inventory to a larger audience of travelers. By doing so, HomeAway is reaching those who wouldn’t normally think to stay in a vacation rental.

Only 35% of consumers report being aware of vacation rentals as an accommodations option today, so marketing has also been a huge contributor to our growth over the years. In addition to social media, search engine optimization, public relations and other components of our integrated marketing strategy, we’ve released several TV ads, including two Super Bowl commercials. Our ads generally compare the HomeAway experience to hotels, which are often too cramped for families to stretch out and truly enjoy themselves. Our newest global campaign uses 360-degree imagery to capture that feeling really well. We’re also interested in the influence that kids have on planning vacations, which has informed much of our recent research and led to a great creative partnership with Kid President, which launched this July.

What industry trends are you noticing and how do you capitalize on them?

We have seen a lot of growth opportunities in emerging markets as internet penetration rapidly increases and attitudes towards renting homes on vacation shift. Therefore, we recently partnered with Dubai’s Department of Tourism to promote the use of vacation homes to the millions of inbound travelers that visit Dubai each year. And last month, we announced our investment in Flat4Day, Turkey’s largest vacation rental website. Many people don’t know this, but Dubai is actually the fourth most popular destination in the world – and the number of visitors to Turkey is growing twice as fast as its hotel capacity. We see the Middle East as a huge growth opportunity for us in the future. South America and Eastern Europe are also regions where we increasingly see opportunity.

We’re also working tirelessly to innovate in mobile, which is a key component of our strategy. To successfully compete with hotels, we need to create the best, most seamless experience possible for our users. We plan on doing so by offering many of the concierge-like services that a hotel would offer on HomeAway’s mobile app. The app already includes features such as instant communication with property owners, restaurant and activity recommendations, and even on-demand services such as Uber rides and one-hour grocery delivery through Instacart. Eventually, our hope is that the HomeAway app will be able to provide almost any service a traditional hotel concierge would traditionally handle – maybe even more.  

Life Motto?

“Keep overhead low and expectations high.” This saying has helped me try to be the best version of myself and improve each day as an employee, a manager and a human.  

HomeAway's Motto?

"The whole house. The whole family. A whole vacation." Vacations are the best time to connect with friends and family to create lasting memories together, and there are functional and emotional benefits to staying in a whole house that a hotel room just can’t provide. There’s nothing like the feeling of being on vacation with all of your loved ones under one roof – that feeling is the reason why HomeAway exists.  

Your greatest success as CRO of HomeAway? Most difficult moment-how did you overcome and what did you learn?

I’ve had this role for three months, so I don’t have many to choose from, yet! In my previous role as Senior Vice President of the Americas, our team’s most significant accomplishment was when HomeAway added the one-millionth property to the site. This achievement was a tribute to our customers around the globe and the result of almost a decade of hard work by an amazing team.

Your advice to an aspiring entrepreneur?

Build a business, not just a product. Express the passion you have for your business and customers in everything you do. Orient around problem-solving and opportunities.

Describe the ideal experience using HomeAway.

At HomeAway, we truly believe that vacation rentals are the perfect setting to create unforgettable memories with friends and loved ones – when you compare HomeAway against hotels, the space, privacy and overall value makes vacation rentals a clear winner. And with over one million rentals on our site, anyone can find the ideal rental for their group, whether they’re looking for a condo in Florida or a castle in Corsica.

For me, the ideal HomeAway vacation would be a trip to New Zealand in a house with enough room for my whole family to relax and have fun. A great kitchen is a must for long, leisurely breakfasts, as is a pool for my daughters to play in. And it helps to have a great TV – a good Netflix binge session after the kids go to sleep makes the experience perfect.

How do you motivate your employees?

I try to set clear expectations, give direct feedback and build a culture where everyone can work collaboratively to achieve our goals.

One food and drink left on earth, what would you choose?

Shrimp fried rice and iced green tea.

What literature is on your bed stand?

There is nothing on my bed stand at the moment, but I often read on airplanes. I love Malcolm Gladwell’s books and sometimes read books on management, pricing theory and other business topics. When I want an escape, I read Harry Potter.

Current passion?

Experiencing the world by traveling to new places and seeing things through my children’s eyes

Favorite travel destination?

Key West, Florida. There’s so much to do and see – and my daughters love it.

What's next for HomeAway?

We’re working on several exciting initiatives to make HomeAway the safest, easiest, most seamless accommodations booking experience in the world. We recently announced that we will be enabling online booking for 100% of our inventory by the end of 2016, in addition to offering secure online and offline payments to our travelers. We’re also working tirelessly to make the HomeAway mobile app even better than it already is by integrating additional functions that will translate into incredible, memorable and effortless vacation experiences for our travelers.