On the Record: Caretaker.com

According to recent statistics, the property management market in the U.S. generates around $88 billion in revenue each year. With more than 70% of property managers performing all tasks from advertising vacancies to tackling maintenance, there are certainly inefficiencies that can occur.

Susannah Vila, founder of Caretaker.com, was a renter that was so frustrated by unreliable property managers that she decided to create a software as a service company that manages rentals.

That company was originally called Flip, using the flip.lease domain name. In 2020, Susannah and her team took the monumental decision to acquire Caretaker.com for $112,000 and rebrand from Flip to Caretaker.

Here, I chat with Susannah about that rebranding process, focusing largely on the Caretaker.com domain name.

Can you tell us a little about Caretaker?

We aim to expand access to rental housing. For us, that means making it easier and more affordable for a renter to get a property lease and for anyone to invest in the housing market. We do this by automating property management.

Replacing most of what a traditional property manager does with software drastically lowers our cost structure and improves the speed and accuracy with which we can find and keep tenants.

You started out as Flip. How did you land on using that brand name, and did domain availability have any part in your consideration?

We began our company with a laser focus on a renter problem, which is that lease terms are rigid, punitive, and rarely fit with a person's life events. The name made sense for renters and allowed us to build a network of renters, but didn't make sense as we started to expand into the landlord market.

When did you first consider rebranding, and why?

It had been in the back of our heads since day one but we only decided to rebrand about 6 weeks before we completed the process.

During the rebranding process, were there any other serious brand name contenders aside from Caretaker?

No - we found Caretaker pretty quickly.

Did you consider the availability of Caretaker.com when choosing the Caretaker brand name?

Our process was to start by identifying .com domain names that were reasonably priced, and then narrow them down into ones that fit our mission. We didn't do it the other way around.

You acquired Caretaker.com from $112,000. How did you go about determining the value of Caretaker.com to your company?

We thought about it in terms of the size of the market that it would allow us to go after, and the amount of share we thought we could get with the right branding.

How important do you think the Caretaker.com domain name will be to your brand in the next 5 years?

The definition of the word is someone who takes care of property. One of the most daunting barriers to entry for anyone interested in owning part of the housing market is figuring who will take care of the property and the tenants.

That part - the hard part - is our bailiwick. Our goal is to scale our ability to "take care" and I think having a name that already describes what we're doing will be a tailwind. I'm excited!

What has been the reaction to your rebrand and acquisition of Caretaker.com so far?

We were fortunate in that many of our customers previous to the rebrand were itinerant. We had staked out a place on the Internet as the place for leaseholders who were stuck in a lease, but since this is something that happens to you once every few years (if that) there was no cause for concern about active users getting upset with us.

The effect that the name has on landlords has been even better than we predicted. As an example, we've noticed that a disproportionate amount of new customers use the phrase "take care of you" when they're introducing us to their tenants as their new manager.

Have you noticed any positive benefits from using a premium .com domain for your brand name? If so, can you share those benefits?

We have noticed benefits from using a premium .com domain that are more qualitive than quantititive. When people are considering using us I think it sounds to them like something that already exists and is established, so there is less fear around adopting something new. This means that we have been able to acquire both traditional early adopter customers and customers who don't fit that mold at all.


Thank you to Susannah for taking the time to discuss Caretaker and Caretaker.com. You can follow the company's journey on Twitter at @caretakermgmt.

These answers have been edited for clarity.