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Implementing your vacation rental software

Implementing new software can be just as involved as opening a new property (except with less travelling). You have to coordinate a lot of moving parts, verify that things are working smoothly, and deal with hidden issues that pop up at unexpected moments. But in the end, it will all be worth it.

We’ll help you approach this process in a logical and organised fashion so that you can get things done efficiently and with as few nasty surprises as possible. And the first step in this process is making a plan. 

Make an implementation plan

An implementation plan will help you lay out what needs to be done, who needs to do it, and how long it will take. It limits the chaos of setting up and learning new software. 

Be sure to do the following when making a plan to implement your new vacation rental software:

Assess resources. Find out how much help you can get, both internally and externally. See if anyone on your team has the bandwidth or expertise to help. If you paid for onboarding, the vendor will assign a customer success person to help you through the setup process. 

Define outcomes. Go beyond simple goals like “get the software up and running.” Be specific. Use dates. Try outcomes like “start accepting bookings on the system by X date.” This way, you have a fixed and measurable target to shoot for. 

Assess potential risks. What could prevent this plan from being completed on time? Is anyone going on vacation? Are there any technical, manpower, or skill issues that could block your progress? Noting them in your plan gives you the opportunity to plan around them.

Set tasks and due dates. No plan is complete without assignments and deadlines. List down everything you need to do and make sure there’s someone covering each item. Set dates to motivate people to get it done—if you don’t, the task will just get shelved in exchange for something else. 

Also check for any dependencies—tasks that can’t be done unless others are finished first. For example, you can’t update listings on the system without integrating all of the booking platforms first. These are potential choke points and should be taken into account. 

Migrating data

If you’ve already been using a vacation rental property management software and have just signed on with a new one, you probably need to migrate your data. 

Data migration means transferring your booking and calendar data from your old software into your new one. There are a few things that need to happen in between, but it’s still a lot better than manually recreating your entire calendar.

Step 1: Export your calendar and listings

All vacation rental software allows you to export your booking data and listings. If you’re unsure where to find these options, consult the knowledge base or ask a customer service person. They’ll be able to point you in the right direction.

Remember to export your data before you cancel your subscription with the old software. It sounds like a no-brainer, but you’d be surprised how many people make that mistake. If you have already canceled, customer service may be willing to do it for you, but there are no guarantees.

Step 2: Format the data

Next step is to rearrange the data into a format the new software will accept. This may mean rearranging some columns or saving the data as a CSV file. Look for some sort of template to help guide you—most vendors will be happy to provide you with one. Again, if you can’t find it in the knowledge base, ask a customer service agent.

Step 3: Import the data

Now you import the reformatted data into the new software. Don’t worry about errors—most vacation rental software will alert you and point out what to fix. Keep at it until all your data is imported successfully.

Once you’ve imported the final file, it’s time to verify the information. Examine your listings very closely for any inconsistencies (you want to be the one to spot mistakes, not your guests). The import might have gone smoothly, but mistakes can still happen. 

Setting up the software

Carefully review preferences and settings before officially launching the software platform so that you can be sure it’ll behave as you need it to. Important areas to configure include:

User accounts for you and your team. Ensure all your team members have gotten their passwords and permissions. You may have to adjust this several times before all your team members get the right combination of permissions.

Integrations to all of your booking platforms. Test and verify that the connections work and data transfers correctly. Also connect important third-party apps like dynamic pricing. 

Automations like automated guest messages and reviews, automated security deposits, and guest identity verification. These are set and forgotten, so you only need to do it once.

Notifications might have to be tweaked before you’re totally satisfied. Try activating all notifications that seem important first and then dial back the ones that get excessive.

Test, test, test

The last thing you want is to officially open doors on your new vacation rental software… only to discover it doesn’t work properly. 

Test the software extensively to make sure it runs properly—especially the booking-related functions. Double-check that you have the right pricing and booking rates, and that your channels are set up properly. Monitor your API connections and integrations to make sure there are no double-bookings or other related issues. 

Get other people to help, too. Send notifications to team members and ask them to run their own tests. Keep an open mind whenever someone brings an item to your attention. Take action on their feedback immediately.

Training the team

Now that you’ve got the software, it’s time for your team to learn how to use it. The question is, who will be teaching them?

If you paid or have access to an official onboarding class, then that question is easy. Get the class curriculum from the trainer. What’s the training schedule like? Is it just one marathon session where everything is lumped together, or is it broken down into several classes? 

If you have a choice, pick based on the amount of free time your team has available. Try assigning people to classes based on their job function. Keeping the subject relevant to them will improve knowledge retention, and (hopefully) leave them with enough free time to work on their regular tasks. 

The same rules apply if you’re going to be the one teaching them. Keep training sessions small and focused. Make heavy use of the vendor-provided learning resources.

Set “check-in” milestones to see how your employees are progressing. Make these milestones public to motivate employees to learn the software, and be strict in enforcing its use. Far too many people slide back to old habits because it’s more familiar—even if those habits are incredibly inefficient.

Lastly, be open to follow-up questions and feedback. Some people will take longer to adjust than others, and they need as much help as they can get. 

Don’t forget to train people outside your core team. Get your cleaners into the habit of looking for notifications, for instance. If your vacation rental software also includes a portal or app for cleaners to check in and post updates, you’ll have to show them how to use that, too.

If you interact with an external stakeholder like a property owner or a client, you will also have to schedule training sessions for them so that they can learn how to navigate their client portals and pull their own client statements.

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Read more about what you need to look out for when assessing what vacation rental software to buy.