The Story

This Keystone Awards is built on the feedback and input from thousands of vacation rental managers.

The Backstory

Terry Whyte & Matt Landau

Ever since their first conversation, Terry Whyte and Matt Landau agreed that the single most exciting area of the emerging vacation rental sector is software: tools that are empowering owners and managers of all shapes and sizes to move more efficiently, profitably, precisely than ever before.

But because the vacation rental software scene is so new, most hosts get overwhelmed trying to decipher it all.

Because there existed no official guide, they decided to showcase some of the industry's finest examples: using an independent vantage point, they began asking which softwares performed which functions best. This led to the creation of a Property Management Software Selector Tool, an Inner Circle resource, which has amassed 2,000+ completions. 

With that data, layered on top of quantitative discussions with our panel of advisors (fellow vacation rental managers who are equally passionate about software demos and innovation) a clearer picture started to emerge: a map to navigate the world of software without driving one's self insane.

Although they are still in this discovery process today (the software learning never rests) Terry and Matt felt confident enough to formally recognize certain companies that were doing standout work in the form of Keystone Awards.

This year, in addition to recognizing property management softwares, VRMB has included some third-party standouts that are doing impressive things.

Why Hasn't This Been Done Before?

There is a fine line between brave and insane and let's just say the Keystone Awards program walks that line delicately.

Trying to make sense out of an emerging landscape is like opening a can of worms with colleagues: both vendors and managers. The criticism, lobbying, and backlash that VRMB opens itself up to is real! But if one of the best ways to discover new tools is through word of mouth...

At the end of the day, the purpose of this research is important enough (to fellow vacation rental colleagues) and no one else is willing (or able) to independently assess the solutions. So Terry and Matt asked...

If we don't get the ball rolling with this work who will? If we don't do it now, then when?

Did VRMB include every great software company in the space? No. In fact, not included are plenty of fantastic companies. The big goal for next year is to have the resources to properly research all of them.

Does attempting to act as a guide sometimes make people more confused? Unfortunately, yes. The vacation rental sector is full of unique profiles we couldn't dream to accommodate every scenario. Instead we had to stick to VRMB's 5 Archetypes. If you have a unique situation that has not been addressed, please reach out (keep in mind, there may be a cost).

Does giving (and not giving) recognition to any given company put a strain on personal relationships? Yes. This is a harsh reality and the single biggest cost of this project: that by recognizing any given company, you're offending others. Many of whom are close friends.

Finally, the team relies on one core belief that staying 100% objective, being ready and willing to update findings based on solid research, and refusing to be influenced, the research program is making a step in the right direction.

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