Cherry Picked!

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

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. Shortly after, Angela began to use Check Cherry to run her business. The benefits of using Check Cherry also include collaborating with clients leading up to their event. "I love how much time Check Cherry saves me. Everything I need for a booking is in Check Cherry. It helps me look like a pro." Using Check Cherry, Angela can offer her customers an easy-to-use and intuitive customer portal where clients can choose backdrops, photo booth templates, and fill out questionnaires.

"Check Cherry is one of the two best values for my photo booth business." Her other top value is Darkroom Booth, a popular photo booth program for operating DSLR photo booths. 

Angela started her business with one photo booth and can now accommodate nine bookings on any given night. "My bookings went through the roof when Check Cherry rolled out proposals because customers had all the information they needed, and with just a click of a button, they can accept and become clients." Check Cherry also offers an option to provide clients a genuine end-to-end online booking for photo booth rentals. "I love getting an email that a client booked without me talking to them."

Check Cherry co-founder Judd Lillestrand said: "Angelas knows how to make her clients happy and close sales. I'm not surprised by her growth. She's been a great customer, provides actionable feedback, and is very likable."

With more photo booths on the way, Desert Memories Photo Booths is still growing. In fact, with the time Angela saves running her business on Check Cherry, she's got the energy to start on a new venture. 

The new company will provide services for Pinterest-worthy slumber parties. "We'll provide Teepees, garlands, pillows, lights, and other cute stuff to make for a memorable slumber party." She also plans to run that business with the same Check Cherry account with a different brand.

Angela is an empty nester and staying busy. With her background in sales and marketing, a Check Cherry account, and a positive entrepreneurial spirit, she's making the most of the newest chapter in her life. "One of the things I appreciate about Check Cherry is they focus on delivering value to businesses like mine. They have the best customer service and manage everything from leads, proposals, billing, taxes, contracts, & event choices like backdrops and template designs."

Do you have a Check Cherry success story you want to share?

We want to hear bout it! Send an email to and tell us all about it.

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. The word means "the highest point in the development of something; a climax or culmination." When Zach started using Check Cherry in 2017, Apogee offered DJ and Photo Booth services. Today Apogree provides DJ, florist, photography, videography, photo booth, casino parties, and planning services. "The system is flexible. It's helped me figure out packages and add all my services.", Zach reflected. 

Zach's noticed the buying preferences of brides changed, and he's ready to capitalize. "We have a more modern, ready-to-book, ready-to-click bride." Zach uses Check Cherry's online booking system to accommodate such customers. "Any service we put on Check Cherry has been booked online.", he continued. Zach is 

"Offering online booking is not only a great way to close more sales, but it's also a great way to collect high-quality leads." Check Cherry co-founder Judd Lillestrand. "That's because people don't want to waste time early on in the evaluation process and want to see pricing and packages. I love that Apogee has a call to action for a 'Pricing Guide .' It sends people to the Check Cherry booking engine. Zach's smart.", Judd continued.

The benefits of using Check Cherry's online booking platform are not limited to allowing customers to book anytime they're ready. If a person does not complete the process by signing a contract and paying an initial deposit, they automatically become lead in Check Cherry. "I love how easy it is to convert a lead into a proposal. We often follow up with someone who didn't finish booking over the phone. It allows us to answer any questions and close the sale by sending a proposal.", said Zach.

👉 Suggested Article: Banquet Hall Booking Form [Tips & Tricks]

Apogee is still growing, too. In February 2020, Apogee started a Wedding Venue in Salem, Oregon. The recipe is simple: provide modern brides with amazing services for just about anything they need. It's a proving ground for the next step in Apogee's journey to becoming the biggest wedding/event service provider in the United States.  

"The team at Check Cherry has been great over the years. There have been so many updates. It’s clear they care about me and my success."

Do you have a Check Cherry success story you want to share?

We want to hear bout it! Send an email to and tell us all about it.

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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February 9, 2021 Judd Lillestrand

5 Tips For Capturing Last-minute Bookings

Accommodating last-minute bookings is a great way to acquire new clients, boost revenue and demonstrate you're ready for business. For some entrepreneurs, a last-minute client can be undesirable. However, by following the tips in this article, you'll be able to shorten your required lead time, capture more opportunities, outperform the competition, and charge more. I'm using the term "last-minute" to encompass the concept of accepting a booking with a tight lead time. Depending on the service, this could be as short as same-day bookings (real estate photography) and might even be a couple of weeks (wedding photography) to be considered last-minute.1.

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January 5, 2021 Judd Lillestrand

Highlights From 2020

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.

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