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Hand-selected articles, guides, and more from the makers of Check Cherry, designed to help your business grow and flourish.

January 10, 2022 Judd Lillestrand

Highlights From 2021

Overall, 2021 was a great year here at Check Cherry: improved market conditions allowed our customers to thrive. While the first quarter was still slow, the rest of 2021 showed substantial booking volume. 


Around this time last year, revenue collected for our customers was down 54.3% Y/Y. That steep drop was the direct result of the pandemic and canceled events. I'm happy to share revenue collected on the Check Cherry platform is up 294.1% when compared to this time last year.


Platform Developments


We made meaningful progress on improving Check Cherry's online booking software last year. Just like the previous years, we listened to you, implemented customer feedback, and laid the groundwork for more exciting changes to come. A big thank you to all of you who took the time to let us know how Check Cherry could be better.


Here are some highlights from 2021:


Payment Enhancements

We redesigned the workflow for making payments and added support for Apple Pay and Google Pay. You can also save client cards and charge them at a later time. We strongly believe payments are a core to Check Cherry and represent one of the more significant opportunities to help our customers grow by making it easy to get paid. In 2022, we want to continue enhancing payment features.


Flex Pricing

Developing a system that encourages a standardized way of selling with packages yet offers enough flexibility to reflect real-world situations is one of the more considerable challenges we face.


In 2021, we introduced Flex Pricing, so you can automatically add surcharges or discounts based on several factors. Common examples include increased pricing for high-demand dates such as New Year's Eve and discounts for bookings scheduled on less demanding dates such as weekdays.


Flex pricing has been a popular feature, and we see more opportunities to help you hone in one of the perfect pricing strategies so you can maximize profitability.


Multi-date Bookings

We finally added support for multiple dates and times per booking. It was a long outstanding feature request, and it required quite a bit of work to make it happen. It feels good to get this one behind us, and we see more opportunities to leverage the underlying changes to make Check Cherry better in the future.


So if you're booking multi-day events or selling two packages to the same client with different start and end times, Check Cherry has a solid solution to help manage more complex bookings.


Custom Booking Questions

Another frequent feature request was to allow you to collect more information during the booking process. I'm happy to say we found a paradigm that meets our need to standardize data and offer high-fidelity software with your need to ask questions specific to how you do business. 


With Custom Questions, you can add optional or required questions to the booking engine. This first iteration is only available during the online booking process, but we plan to bring them to proposals and mini sessions in the future.


Date Only Scheduling Mode

Most of you bill hourly or at a flat rate per package. However, some charge a daily/weekend rate for event space or equipment rentals. In 2021, we added a new scheduling mode allowing for packages to bill based on a daily rate. We're always excited about expanding the usefulness of Check Cherry and look forward to seeing how this feature develops in 2022.


Unit-Based Pricing

A common feature request from event space owners, real estate photographers, and caterers was an elegant solution to vary pricing by quantity, such as guest count or square footage.


New in 2021, you can now configure packages to charge based on Unit Pricing. This new option also works well with Check Cherry's add-on system and allows an opportunity for add-on prices to increase as the number of units increases.


Better Mini Sessions

In 2021, our mini session scheduling feature set continued to improve. For example, you can now sell add-ons with mini-sessions giving you another option to help maximize revenue. We also added the opportunity to offer discount codes giving you another marketing tool to sell better. Check Cherry's questionnaires were also brought to mini sessions, so it's easy to collect more data after the initial booking. We made the process of rescheduling mini sessions a lot more intuitive, and mini session clients can now save a card on file for future use.


Performance Improvements

Fast page load times matter, and I'm happy to share 95% of Check Cherry web requests are complete within 735ms or less. That's the result of work we performed in 2021, including improved image processing, upgraded servers, more robust message processing, and more. 


Reporting Upgrades

Giving you excellent access to your data has always been important to us. This year we added support for saving reports for frequent access. We also added shortcuts to standard periods such as "Last Quarter", "Last Month", and "This Year". There were also several smaller changes such as sorting by booking total and filtering by staff or customers account.


Better Booking Attachments

We enhanced features for attaching files to bookings adding both client-level and staff-level permissions. You can now add attachments to be seen only by staff members or admins. You can also add an attachment that links to a document stored in the cloud, such as Google Drive, which is a great way to share a document such as a staff guide while managing it in one place.


QR Codes Everywhere

It seems like QR Codes have officially hit the mainstream. In 2021, we added the option to insert QR Codes in Automated Messages, and anywhere you can copy a link in Check Cherry, you can also generate a QR Code. So if you are looking for an easy way for people to start the online booking process in person, just grab the QR code and drop them right into the booking engine.


Questionnaire Improvements

To reduce confusion, we renamed Forms to Questionnaires. We added signature and file upload field types as options for your clients and staff to complete. We also added an option to upload an image as a label, giving customers more context when filling out a questionnaire.


New Integrations

Check Cherry integrated with the popular photo booth backdrop provider PB Backdrops in 2021. Now you can pull in hundreds of awesome backdrop designs to give your clients more options. You can also set prices for all backdrops in a category, so it's easy to charge extra for any backdrops you don't already own, but include the ones you already own for free.


Better Client Accounts

We enhanced features for user accounts, and you can now add multiple client accounts to a booking. Furthermore, there are options to hide pricing for client accounts and prevent a specific client from receiving automated messaging, which can be used to give wedding planners and other third parties access to the booking.


Easier Automated Messages

We updated the UI for managing Automated Messages. With tags and previews, it's now easier than ever to review, preview and organize your email and text message templates. We also added the option to pull in some templates when manually crafting a new message from Check Cherry.


Proposals Builder Enhancements

The process of building proposals is easier than ever. Check Cherry is now more thoughtful about which options will be shown and required based on your package settings.


Tons of smaller stuff

As usual, much of the software development work completed was smaller in scope and not highlight-worthy. However, these minor changes add up in significant ways, and over time they make Check Cherry more enjoyable, more reliable, and just overall better.


Looking at 2022

We're excited about 2022. Check Cherry has come so far over the years, and we'll have an opportunity to continue improving our service and making it even better. 


Thank you for being a customer and helping us create something unique. We love seeing our customers do well and are excited to introduce new ways to help you thrive in 2022. 


September 20, 2021 Check Cherry

7 Tips For Better Mini Sessions Flyers

Selling out your mini sessions is key to making them an effective of your photography business. It's also great marketing because it shows people you are in high demand.


The first step in selling out your mini sessions is to get the word out to your audience. Often, this means posting advertisements online and sending a flyer via email to past clients. In both cases, this first impression of your mini sessions will make or break them. 


In this article, we'll cover practical tips for making your mini session flyers more effective so you can book more clients.

Promote The Location

Your mini sessions should be convenient for both you and your clients. By advertising the photoshoot location, you'll help people know how far of a drive it will be for them. 


Share The Date(s)

Along with the location, people will need to know which date you plan on hosting your mini session. If you have multiple dates for the same theme, make it clear there are options.


There is no need to get bogged down and list specific time slots. Leaving a reason for people to learn more is a great way to gauge interest.


Make The Purpose Clear

The best mini sessions have a purpose or theme. Let people know why they need to stop what they are doing and book a slot by today. For example, is this an excellent opportunity to get pictures for Christmas cards? 


Suggested article: Ideas For Mini Sessions


Provide A Sample

One of the most effective ways to convey the value of a mini session is to provide a sample photo of what one should expect from participating. While many mini session templates online have slots for multiple images, we recommend leading with one great photo. It will help your flyer feel less cluttered, be more prominent and give you room to focus on other important details listed in this article.


Include Deliverables And Price

Provide a brief description of what is included with the mini session, along with the associated cost. Common deliverables are the number of finished images, usage rights, and turnaround time. While it's wise to offer optional upsells as add-ons, you should avoid cluttering up your flyer with too much info and show more options later in the sales process.


Include A Call-to-action

Now that you've given people enough information to let them know if it's a good fit, it's time to let them know how to proceed. Don't be coy or shy here; include short instructions covering how one can book. Call-to-action examples include:


"Text to book | 555-909-2360"

"Call For Avalalbity | 555-415-1212"

"Book Online Now | https://rainier.checkcherry.com/mini_sessions"

"View Available Slots | https://rainier.checkcherry.com/mini_sessions"


Offer Online Scheudling

Let people know that securing a spot is hassle-free by using a quality mini session scheduler like Check Cherry. By showing the real-time availability of time slots, you'll save clients the frustration of going back and forth to secure a spot. You'll also be able to display optional add-ons during the booking process, which leads to more money in your pocket.




August 23, 2021 Judd Lillestrand

11 Tips For Sending Proposals Clients Will Accept

Sending online proposals can be an attractive way to present your services. Done well, they make it easy for someone to finalize a purchase by signing your contract and paying an initial deposit/fees. With the tips in this article, you'll be able to level up your proposals, so they become a highly effective part of your sales process.


👉 Some people refer to proposals as quotes. For the most part, people use these terms interchangeably. 


1. Understand your prospect's needs.

The first step in presenting a highly effective proposal is understanding the needs and desires of those looking to hire your company. After all, the goal is to provide an offer they are likely to appreciate.


Before crafting a proposal, start with a friendly conversation to learn more about your prospect's wants and values. Be genuine and establish yourself as a guide by asking questions to identify whether or not it's a good fit. These conversations are your opportunity to demonstrate the caliber and quality of your company.


👉 Remember, not everyone is going to be a fit. It's ok to turn down an opportunity and focus efforts on those more likely to book by not sending a proposal.


2. Leverage multiple communication channels.

It's good to nudge a prospect to your preferred communication method, but let them know you are open to other ways of communication. Avoid forcing a client to communicate over one specific medium (phone, text, email, etc.) because it's how you want to sell.  


👉 You can increase the chances of people responding, feeling comfortable, and trusting you by using their preferred method of communication. 


3. Make your proposals easy to understand.

A shorter and more straightforward proposal will perform better than a proposal with unnecessary content and fluff. Unless you respond to a lengthy Request for Proposals (RFP), it's best to skip the clutter. For example, there is no need to sell your company at this stage. Your marketing collateral/website and sales communication leading up to the proposal are the places to make that happen.


4. Make the look great on phones.

Whether you email or text your proposal, the chances are good it will be seen first on a phone. Avoid sending pdf files and word documents because they just won't look good on phone.


4. Add imagery.

Including pictures of your packages and add-ons will go a long way in helping people understand what you are offering and make them feel more comfortable. Include photos of your packages, add-ons, and any other relevant information.


6. Offer a complete breakdown of costs.

Be sure all costs, including tax and travel fees, are disclosed upfront on the proposal before the client accepts the offer. You risk losing trust and annoying a customer if you add more fees/tax after presenting your offer. 


👉 Word of mouth is a great way to grow your business. When people have negative experiences with your company, they are much less likely to refer you, and many will never tell you about it.


7. Add your brand to each proposal.

Add your company's logo to each proposal. You can even take it a step further by incorporating your company's color scheme. It will go a long way toward making your company look professional, trustworthy, and ready to do business. 


👉 People will judge the quality of the services you will provide based on how your sales process goes. If they get the sense, you are not professional and organized; you'll lose sales. When you look like a pro, you'll be able to charge more.


8. Make the acceptance process easy.

With few exceptions, the days of printing, signing, and faxing documents are gone. Digital signatures are the standard. Be sure to provide a call-to-action and easy workflow for securing your services. Often that means signing a contract, paying a deposit.


9. Offer multiple payment options.

If a deposit/fee is required for securing your services, make it easy for people to pay. The payment step is when most sales are lost. By making it easy, you'll increase the chances of closing the sale.


👉 Use a quality online booking website like Check Cherry, which supports Apple Pay & Google Pay to make the process of collecting a deposit quick and easy.


10. Give time-sensitive discounts.

Expiring discounts are a tried and true way to motivate your prospect to make a decision and commit. If you offer a discount, be sure to put a short time limit for accepting the offer. A few days is a great place to start, and you can adjust based on your observations.


👉 Keep in mind, you can honor the expired offer if they are willing to commit shortly after the initial expiration. Favors are a great way to establish goodwill with clients.


11. Follow up.

If a proposal is not accepted or declined, it's a good idea to reach out and check-in. Another benefit of offering a time-sensitive discount is it will give you a sensible reason to follow up in a day or two, and it sets expectations on when someone will make a decision. 


Avoid over automating your follow-up and sales process. Anything over a couple of touches is probably a wasted effort which is more likely to make your company seem impersonal and out of touch. Try crafting personal messages to increase the chances of people responding. 


👉 A a quality online proposal system like Check Cherry will show you if someone has viewed your proposal. 


Bonus Tip


12. Compliment proposals with online booking.

Avoid sending proposals to every lead without a conversation. It's a sure-fire way to decrease their effectiveness and will dilute your follow-up efforts. Instead, use a quality online booking website like Check Cherry to accommodate a lower-touch, self-service sales process. You can even direct people who want to see your pricing guide and collect leads for those who start but do not finish the booking process.


August 5, 2021 Check Cherry

Photo Booth Success Story: Angela & Desert Memories Photo Booths

When a sales and marketing pro with 25 years of experience decided to start a photo booth business, she knew the buying process needed to be smooth if her newfound company were to flourish."I first started looking for solutions because I wanted an easy way for my clients to sign contracts and pay.", said Angela Flores of Desert Memories Photo Booths. After using more traditional solutions, she found something that worked well. "Check Cherry does such a great job at making my sales process efficient. I've doubled my business each year (less covid's 2020), and I truly believe Check Cherry played a role in my ability to do so."Angela started Desert Memories Photo Booths in 2017 to service the Tucson and Phoenix photo booth rental markets.

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August 2, 2021 Check Cherry

Wedding Venue Success Story: Zach & Venue APOGEE

When a seasoned entrepreneur wanted to take his event service company to the next level, he knew he needed to find the right system to help along the way. "At the time, I was spending a lot of time sending emails to clients. I came across a video of Check Cherry's automated messaging on social media and decided to sign up for a trial.", said Zach Thomas, CEO of Apogee, an Oregon Wedding & Event Services company. "I attribute a lot of my ability to grow the business to the time I save with Check Cherry. It allows me to focus less on repetitive tasks and more on the bigger picture."Zach has big plans. It's no misnomer he named the company Apogee.

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June 14, 2021 Judd Lillestrand

Going Viral On TikTok: Dollop Photobooths & Mini Sessions

At Check Cherry, we love getting to know our customers, and it's extra fun when they share their success stories. This article is about Dollop Photobooths, their fantastic photo booth concept, and how they used Check Cherry's mini session scheduling feature to pull it off and scale up after going viral on TikTok.The ConceptRent a pop-up studio space in a convenient central location.Dollop chose Cross Street Exchange, a famous work & leisure hub with a high-rise office building & old shophouses turned into stores & eateries.

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March 30, 2021 Judd Lillestrand

14 Reasons You Need A Photo Booth CRM

Performing a job well done at the event is an essential part of running a successful photo booth business and making clients happy. However, experienced entrepreneurs know most of the work in running a successful photo booth business happens before and after each booking. That's where a Photo Booth CRM can help you book more clients, manage bookings and automate a lot of the boring stuff you don't like doing.What is a Photo Booth CRM?CRM is an acronym for "Customer Relationship Management". A Photo Booth CRM is a system designed specifically with the needs of those providing photo booth services to customers.

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March 26, 2021 Judd Lillestrand

$25,000,000 Booked on Check Cherry

Recently, we passed a milestone: $25 million in bookings on Check Cherry. In late 2017, we crossed the 1 million in bookings milestone. Check Cherry's booking and client management system has come a long way, and we've our customers to thank for helping us get here and improve the service. We're excited about the future and know there is still a lot of room for growth and improvement. We'll keep working hard to help make customers successful and can't wait until the next milestone.

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March 16, 2021 Judd Lillestrand

Use Modern Payment Options To Increase Sales

In this article, we're going to give you some tips for happier, healthier, smoother payment processing so you can make it easy for customers and get more bookings.Clients will love it when it's easy to do business with your company, and one of the more critical aspects of running a smooth operation is making it easy for clients to pay their deposits and balances. At times, payments can feel awkward, painful, and downright discouraging. Thankfully there are a lot of options for collecting payment today, and they'll make both you are your client's life better.Focus on making it easy for your clients.If you make it easy to pay, more people will book you online and accept your proposals.

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March 5, 2021 Judd Lillestrand

Photo Booth Booking Forms [Tips & Tricks]

When you're ready to start accepting bookings for your photo booth rental business, it's essential to collect the right booking details to ensure the job goes smoothly, the client is happy, and your business gets more 5-star reviews.In this article, we'll cover some best practices for collecting information when booking photo booth rentals. With these tips, you'll be off to a smooth start and avoid common mistakes we see new photo booth entrepreneurs make when taking bookings.Event Type and Desired PackageAllow people to indicate the type of event they are hosting and the package they would like to purchase. Only show them the packages which are available for their type of event.

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