We’re building the operating system for rental housing.

Getting millions of property owners to entrust their assets to our algorithms won't be easy. We'll need exceptional storytellers, relationship builders, product designers and engineers.

If that's you, join us.

Open roles

We're actively recruiting customer support associates, product and engineering leaders. If you think you might be a good fit, send us a note.

Why Caretaker?

We work a bit differently here.

We value deep focus over collaboration

Collaboration is necessary and can be great, but we're wary of too much of it getting in the way of productivity. At Caretaker, you won't be in meetings all day. We meet as infrequently as possible, try to do it as efficiently as possible and rely heavily on asynchronous communication tools like strategy memos. It follows that you can work whatever hours are optimal for you.

We value small, high impact teams

The Harvard Business Review found in 2019 that smaller teams were more likely to disrupt current ways of thinking. We select few, extraordinary people to join our team. We give them more ownership and freedom in their respective roles than their counterparts at similar companies.

We value saying no

We don't want to build everything for everyone - we're always finding new ways to focus our energy and time on a smaller group of higher impact tasks. Saying no to feature requests is as important as choosing the features we do decide to work on. You won't find our engineers spending hours on support for Internet Explorer 8.

We want you to work on things that excite you

Even the most exciting core responsibilities can become humdrum after a few months, that’s why we encourage our team to spend 20% of their time on something new that gets their creative juices flowing. Even if you don’t take us up on this, we have hackdays where regular work is frowned upon.


A small team means we have more flexibility than most. At Caretaker you’ll get to pick out whatever tech setup you prefer - from computer to monitors to headphones to keyboard and mouse, whatever works best for you, we'll get it. We've been remote-first since day 1, so we're here to help with tips on setting up your remote or mobile office. We also cover the basics:

  • Medical, dental, and vision insurance

  • Gym membership

  • Unlimited vacation

  • Stipend for home office