Q&A with Steve Milo

People, Innovation & Technology, Vision & Success

Q&A with Steve Milo

“Trust your instincts. Don’t just listen, focus on processing not what people say, what they do.” – Steve Milo, CEO of Jackson Mountain Homes

We asked Steve Milo to answer questions on a few topic areas:

People, Innovation & Technology, Vision & Success


What qualities do you look for generally when hiring?

Since we are entrepreneurial, we look for people who can handle a dynamic and fast environment. We are looking for people who can adapt and evolve. We can be unstructured and need people who have a lot of energy who are autonomous, yet, collaborative.

What do you look for when hiring for a specific role?

Experience in the vacation rental is not necessary, we do find with owner acquisitions, previous experience does help. Being able to talk to an owner and understanding issues that come up is key along with a clear understanding of hospitality. For many owners, their homes are a major investment, they often have questions on maintenance, pricing, bedding, remodeling, and we have to be knowledgeable to speak with them.


Business school teaches us to keep innovating. What should property managers be focused on to build their business?

Gain the most return from technology. Companies have competitive advantages in real estate, vacation rentals, e-commerce, and food delivery. Innovation needs to be adoptive and adaptive. We use software to drive people online rather than picking up the phone and we provide information to the consumer so they don’t have to interact with people.

We are focused on using more smart home technology and going electronic vs picking up the phone.

Jackson Mountain Homes rating system is a unique innovation, can you tell us about that?

Our rating system was created because our guests would have different experiences and we created a standardized guest experience. This playing field lets the owner know how their property measures up.

How do you prepare your team to deal with change and transformation?

We take on at least one big initiative every year, this year, changing property management systems, laundry, rating systems, and keyless entry. It’s important not to overwhelm your company. We have meetings, and start discussing programs right away. We have a culture of understanding and evolving.


Where do you see the industry headed? Any predictions for the future of the Vacation Rental Industry?

More and more consolidation. Companies more effective with technology are going to be much further ahead. There will be more keyless access, remote deposits, ACH, anything eliminating human interaction.

What does success look like to you?

Running an efficient business as far as serving guests, owners, and shareholders. We plan for change. Things can break or you outgrow them. This is what makes technology so interesting, it can solve problems created by growth.

How do you create consistency?

Take a look at the process. Look at what is broken and figure out what is the biggest return you are going to get.

Why did you choose to grow such a large company instead of staying small?

Diversification, I thought we would be in a much better situation. Synergy, economy of scale. Gain it by size, try to leverage it. Ultimately you can have a higher level of professionalism.


What was your worst job ever?

Working at a bakery at a mall, in a kitchen in the basement, it was a dungeon. We had to scrub grease covered pans with Brillo pads. We spent hours scrubbing and scrubbing and even had a pet rat who would visit.

What is your favorite place to vacation?