7 reasons why new online booking software feels overwhelming for water sports rental businesses

By Brieanne Biblow

Booking ManagementBooking Management

Illustration of a frustrated woman in a red top and yellow pants sitting at a desk looking at a laptop with an online guest booking system

Change is scary. That goes for everything in life, but especially in your business. 

For most seasonal rental operators consistency is key – like knowing what booking volumes to expect in your high season so you can plan accordingly for your low season. 

So it makes sense that disrupting your business’s flow with an overwhelming change like upgrading your booking system isn’t at the top of your list. 

We know getting started with a new watersports rental booking software can feel overwhelming. But whether you rent kayaks or canoes, surfboards, or sailboats, the benefits of switching are huge. 

Just imagine, your customers will be able to self-book water sports rentals online 24/7, without waiting for you to email back or pick up the phone. 

On your side, you can keep track of equipment in real time. No more clicking through a spreadsheet to see what’s available or relying on pen and paper. The benefits go beyond bookings, too. An online booking system tracks waivers, sends automatic confirmation emails, and drives more revenue with unique pricing features.  

It sounds intimidating, but it could be exactly what you need to run your business efficiently.

To hopefully dispel some of your fears, here are seven reasons you might be hesitant about using new online booking software — and solutions for each one.  

7 reasons why a new online booking software might feel overwhelming

When you’re running a water sports rental business, bookings are everything. It’s how you make money after all. Let’s walk through what might be putting you off switching your online booking software and how we can help. 

1. Lack of familiarity 

If you’ve been using a booking system for a while, you’ll know all of its nuts and bolts — especially if you built a system from scratch to suit your needs. 

You may not know how to implement a new online booking software into your business. And even if you do, switching watersports rental booking software providers means having a whole new system to get up to speed with. 

The solution: You don’t need to figure out new software alone. With Checkfront, our team of onboarding specialists can walk you through how to set up and use our software. You’ll hit the ground running and get back to serving your customers. 

2. The learning curve

Once you’re set up with a new online bookings system, there’s still a learning curve. You’ve got to figure out how to take bookings, customize digital waivers, and allocate your assets. It can feel like learning to speak a new language. 

Let’s flip the script here, though. Changing habits can be hard, but it might be necessary. Clunky self-made systems or unorganized filing cabinets probably need to go anyway. 

Learning a new way of running your rental business could be the thing that helps it grow. And it’ll save you a lot of time and stress in the long run. 

The solution: Learning curve meet Checkfront’s simple set-up guide. It will walk you through how to set up your products, customize your booking page, set up automated emails, set up online payments, and more. Plus, if you learn best by reading, our robust knowledge base is packed with resources to help answer your questions. 

3. Technical support availability

Integrating new technology into your business can be overwhelming even when everything goes well. So when you hit tech issues, we know the stress levels creep higher. 

And when software hiccups happen, you don’t want to be left in the lurch without technical support. 

The solution: Our best-in-class technical support team is always on hand to troubleshoot issues fast. They can answer any questions that come up, and share detailed videos showing you how to get you back on track. 

4. Integration challenges

You might already have software tools you know and love, whether that’s for accounting, payments, or analytics. So, you want to be sure that any new online reservations software is going to play nicely with your existing tools.   

The solution: Checkfront integrates seamlessly with several software tools you might already be using. That includes Quickbooks, Stripe, Google Ads, and MailChimp — just to name a few. 

5. Customization complexity

One of the pros of moving your booking systems online is that you can customize everything to fit your business needs. On the other hand, one of the cons is that this customization can take time.

While time-consuming, customizations can lead to better workflows and new ways to drive revenue in your business. 

With any new software, you can offer features you weren’t able to before, like upsells right at checkout. For example, want to offer a discount on fishing rods when customers charter your boat or upsell a bottle of champagne? That’s now one click away with an easy add-on. 

group of 8 adults whitewater rafting on rapids

The solution: Checkfront is the most flexible online booking system out there. But don’t just take our word for it. Explore our built-in features like automatic email notifications and seasonal pricing. There are even flexible booking options, so guests can rent equipment daily, multi-day, by timeslot, or with flexible start and end times. And there’s no risk of double booking.

Tight on time? We’ll do the hard work for you. Our team of implementation specialists will completely configure your account with all the customizations you need. Or, if you took over Checkfront from a previous business owner, our specialists can run training for you and your team. 

6. You’re unsure about features

From stand-up paddle boards to boats and jet ski rentals, your business is unique and complex. So you might be wondering if an online booking management system can do everything you need it to. 

You don’t just want to take bookings. You want to manage inventory, track Facebook ads, pre-schedule emails to collect reviews, and see at a glance who’s signed your rental waiver and who hasn’t. 

The solution: Checkfront is built for water sports rental businesses like yours. We’ve spent 15 years building our product with more than 5,000 customers. With their help, we’ve created robust features to cover everything you need — and a lot of things you didn’t know you wanted. 

Whether you want to take more bookings, maximize your resources, or more effectively run your business, we’ve got features to make it happen. And because your business is always evolving, we’ve launched our Idea Portal. Here, you can share which features you’d like to see next. 

7. The price

New software comes with a price tag, and this can be intimidating. Evaluating different softwares and comparing price points can often leave your head spinning. But as you know, you need to spend money to make money. Good software is one of the best investments you can make for your business. 

The solution: For water sports rental operators, our Growth Plan is the perfect fit. It comes with added features like unlimited bookings and waivers and the lowest booking fee model on the market.

A white box with text inside that shows pricing for Checkfront's online booking software.

Final thoughts 

Setting up online booking software for the first time — or switching booking software providers — can feel overwhelming. There’s the time, the tech, and the price tag to think about. 

With Checkfront, you don’t have to figure this all out alone. Our team is on hand to get you set up quickly, help train your team, and offer flexible pricing options. 

Plus, Checkfront is the water sports rental booking software that’s as unique as your business. We’ve got customizable features to suit your needs. So whatever you rent, and however you want to rent it, we’ve got the tools to help. 

Make the switch (easily) to Checkfront today

Online bookings. Flexible pricing. Outstanding support.