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Highlights From 2020

January 5, 2021 Judd Lillestrand

It's time for another annual recap. There's no way around it: 2020 was a rough year for most of Check Cherry's customers. A prolonged pandemic, restrictions on gatherings, and general uncertainty resulted in fewer bookings for our customers.

Adversity aside, at Check Cherry, we were still able to make substantial progress in improving the platform during 2020. We're grateful for all the feedback and ideas you shared with us to make Check Cherry better. The pandemic shifted our development priorities, and I want everyone to know we worked hard to adjust and help you navigate the market's challenges.

Here is a quick recap on how we Check Cherry platform improved over the last year:

The Postpone Status

Our first feature in response to the pandemic came mid-March as cancelations and postponements started rolling in. We added a Postponed status for bookings. By marking a booking as Postponed, it made it slightly easier to navigate the pandemic, stay organized, and salvage one's current book of business.


Check Cherry now allows for your account to operate with multiple brands. While this feature had long been on our list of things to offer, the pandemic made it a higher priority because many of our savviest customers branched into other services to diversify their business and keep earning.

Contracts [Enhancements]

Getting clients to sign the right agreement is essential, and over the years, we've had many feature requests/ideas in this area. In 2020, now you can set up multiple contracts, insert data based on package or add-ons purchased, and dynamically add merge tags—essential features for those operating various brands and offering unrelated services.


Check Cherry is excellent at helping service entrepreneurs stay organized. With Checklists, you can build multiple lists for each booking automatically. This feature is perfect for creating pre-bookings todos, equipment checklists, and deliverable reminders. You can also add a list for your clients to help guide them through the process of working together.

Google Calendar Integration

A lot of Check Cherry customers operate their business while holding a full-time job or earning elsewhere. Check Cherry's Google Calendar allows solopreneurs to automatically block off company availability based on events they add to their Google Calendar.

Mini Sessions [Enhancements]

This fall, we received a lot of great feedback on the mini session scheduling features of Check Cherry. We reworked the feature in many ways to make it easier to use, more powerful, and more integrated into Check Cherry.

Message Queue

We believe business automation helps people free up time to connect on a more personal level with clients. You can now automatically generate an email or SMS/text messages for a booking but hold it in a queue for later review. At that point, the message can be manually reviewed, edited, and send out with a click by personalizing messages to a client meaningful impact on their effectiveness. 

New Online Scheduling Modes

The pandemic resulted in more of our customers offering services that are not anchored by an inflexible event/wedding date. People needed a way to let prospects easily browse their availability online before picking a date. We're happy to say Check Cherry now offers customers the ability to choose slots and tools for you to specify slot availability.

Booking Engine [Enhancements]

Online booking and scheduling are core to Check Cherry. In 2020, we were able to focus a bit more on the booking engine. You now have more control over the look and feel of the booking engine colors so they can better match their brands. One can direct someone away from online booking and into a traditional Contact From to collect leads for high-touch sales such as corporate bookings.


It's common for our customers to provide services at the same places throughout the year, from popular wedding venues to their favorite photo shoot locations. Customers can now store those places in Check Cherry and add pubic and private notes. One can even include Places as a step in the online scheduling process, allowing clients to select a location while booking online which is great for booking photography clients online.

Calendar Refresh

The calendar is one of the most used features of Check Cherry. We distilled years of feedback to rethink how to make it better, from seeing Leads on your calendar to spot a hot date to better search capability and even some helpful filters to find specific bookings.

SMS Messages

We consistently received feedback from customers who wanted to send SMS/text messages just like they send an automated email. I'm happy to say in 2020, we got it done by integrating with Twilio to send the messages. Now one can send important staff reminders, proposal invitations to clients, and any of the other hundreds of combinations that else Check Cherry's powerful messaging automation provides.

Proposals [Enhancements]

Check Cherry's proposal system is simple, elegant, and highly effective. It's a feature that is heavily used to generate sales, and we made it even better in 2020 by adding the option for a client to choose add-ons and/or backdrops before accepting the proposal. Also, Proposals can now show staff members assigned to work the booking to help make a human connection and drive more sales.

Hourly Add-ons

Our customers frequently vary the price of services based on the length of a booking/event. We added a new option allowing add-on pricing to be calculated on an hourly basis. 

A bunch of smaller tweaks and changes

There were over 1600 commits/changes to the CheckCherry platform in 2020. Many of those changes were small tweaks or improvements to the underlying platform, which most people will never explicitly notice. However, all those little changes add up to help make Check Cherry easier to use, more powerful, more reliable, more enjoyable use as a customer, and more fun to build as a developer.

Looking at 2021

Internally, we're optimistic about 2021, the COVID-19 vaccine is rolling out, and we expect to see pent-up demand for our customer's services emerge in the coming months. The pandemic has really highlighted the value of getting together and the incredible role it plays in everyone's well-being. 

Thank you for the continued support and for allowing us to play a role in helping you grow, manage, and delivering fantastic client experiences. 

Good Riddance 2020. Happy New Year! 

People will ❤️ how easy it is to book you online.

Try Check Cherry free for 14 days, no credit card required.

Try Check Cherry free for 14 days, no credit card required.

⭐⭐⭐⭐⭐ "I love it!"

"I found Check Cherry when doing a search for something to schedule mini sessions for my photography business. It's the perfect end to end online booking and payment solution. I has made my work so much easier, and its convenient for my clients to click to select their session, sign the contract, and pay. I love it! Not to mention, their customer service is on point. Quick response time and open to suggestions. Fantastic!"

~ Cammy