Skyler360 is much more than auto-responders and recordings. The patent-pending technology is eerily close to artificial intelligence.

  • Buyer agents are being provided an ever-growing suite of tools to automate critical steps in their process.

Have suggestions for products that you’d like to see reviewed by our real estate technology expert? Email Craig Rowe.

Skyler360 is an automated lead management system.

Platform(s): Browser-based, agnostic
Ideal for: Agents and teams looking to improve prospect screening and mobile marketing

Top selling points

  • Automated follow-ups
  • Highly detailed transaction step tracking
  • Customization of email and text scripts

Things to consider

The software is all about productivity, not looks. It’s like a pre-2015 Subaru WRX — hard to look at, but impressively capable.

Full review

Skyler360 was developed out of the need for better screening apartment tenants.

Ron Sasson asked himself, how can a landlord limit his or her time interacting with unqualified tenants?

The solution was to not interact with them at all.

Skyler360 automates the early steps of lead cultivation by communicating with prospects via text and email.

Each response by the potential buyer initiates another Skyler360 response, and thus further qualifies the person’s level of interest until he or she commits to an appointment.


This is much more than auto-responders and recordings. The patent-pending technology is eerily close to artificial intelligence.

Everyone knows that a text sent back in five seconds is a robot. Or a high school student. To remedy that, Skyler360 waits two minutes to respond to simulate the pace of natural human interaction.

The whole process starts with a phone call or website form response. Multiple properties set up within the system use numeric codes printed on sign riders.

Everyone knows that a text sent back in five seconds is a robot. Or a high school student.

While automated voice tours and text codes aren’t new, Skyler360’s ongoing conversation capability makes it unique.

The first text asks for an email address. When submitted, the prospect gets an email with a branded response and property flyer. When they open the email, another text is triggered with a link to an online calendar with open tour dates.

After a prospect chooses a date and time, another confirmation is sent. It connects with your Google Calendar so it knows when you are available.

Every step is tracked automatically in Skyler360.

You can walk out of a meeting and have three new showings confirmed in your calendar without ever having looked at your phone or logged in to anything. It also captures phone numbers and in many cases, names.

Every point of communication can be customized. Skyler360 sends a different talk track when an individual responds as an agent or buyer.

Users can also add to their messages links to online tours or other branding elements, maybe a PointDrive page. Skyler360 gives one an attentive audience.


The automation is impressive, even if the backend interface is woefully lacking. The inherent value trumps the look and feel though, and I don’t say that often.

There are some value-adds here, too. Skyler360 can work with your website to initiate leads from MLS listings.

If you can get a buyer to register and save a search profile, Skyler360 will automate that, too. As matching listings come in, the system will work the buyer until moments before you drive up to the listing.

The company has partnered with DocuSign to add a range of agreements, as well. Naturally, they’re sent via text or email links, just as you would do.

Exception handling is easy. If a person texts back a random question outside of the context of the specific property, Sklyer360 sends a “Can I get back to you on that?” message, or something similar.


The system dashboard lets you see where every message thread begins and ends so you can take over manually if needed. It’s a true acorn-to-oak tree process.

If you have an account with an automated research tool like Charlie or Nimble, which pull online profiles from names in your Google Calendar or inbox, a good portion of prospect due diligence can be done for you as well.

There is also the possibility of integrating ListReports, a text-based marketing content delivery tool. also automates showing appointments.

Having not seen the tool up-close (Inman’s Andrea Brambila reported on it in 2013), I can’t tell you to what level its communications can be customized or if it automates the activity tracking like Skyer360 does.

I do know that Skyler360 is a work in progress. But the progress I’ve seen makes it a worthy competitor.

And suddenly this column is making me look more and more prescient.

Have a technology product you would like to discuss? Email Craig Rowe.

Show Comments Hide Comments


Sign up for Inman’s Morning Headlines
What you need to know to start your day with all the latest industry developments
Thank you for subscribing to Morning Headlines.
Back to top
Time is running out to secure your Connect Now tickets at the lowest price. Don't miss out on a chance to grow yourself and your business.Learn More×
Up-to-the-minute news and interviews in your inbox, ticket discounts for Inman events and more
1-Step CheckoutPay with a credit card
By continuing, you agree to Inman’s Terms of Use and Privacy Policy.

You will be charged . Your subscription will automatically renew for on . For more details on our payment terms and how to cancel, click here.

Interested in a group subscription?
Finish setting up your subscription