What I like best about CheckCherry is how much time it saves me while keeping my business organized. Everything I need is in one place—lead management, contracts, invoices, payment processing, automated emails and text messages, scheduling, and client communication.

I also love that the platform is constantly evolving. The team is always adding new features, especially the recent AI integrations, which show they're committed to staying ahead of the curve. On top of that, their customer support is second to none. Whenever I've needed help, I've received fast, knowledgeable, and friendly support.

The best part is that CheckCherry is extremely customizable while still being easy to use. I've tried other CRM systems, and none have matched the combination of simplicity, flexibility, and powerful automation that CheckCherry offers. Review collected by and hosted on G2.com.

I don't use their forms for music collection as I have found other softwares that fit my needs better. Review collected by and hosted on G2.com.

Instead of sending multiple emails and documents back and forth, our clients receive one link where they can review their proposal, choose add-ons, sign agreements, make payments, and receive automatic confirmations, receipts, and payment reminders. The entire experience feels professional and has significantly reduced the amount of administrative work for our team.

What really separates Check Cherry is how well it works for entertainment businesses. It feels like it was designed with companies like ours in mind instead of trying to adapt generic CRM software to fit our needs. Review collected by and hosted on G2.com.

The only downside is that there can be a bit of a learning curve when setting everything up, but the onboarding and support from Matt and Judd made the process much easier. Review collected by and hosted on G2.com.

I love the personal aspect of it the most. We can talk to the owners Judd and Matt to talk about how to better improve our way of using it. They are so eager to help and always looking for feedback on how to improve the system. We always feel heard and understood. We also love how easy it is to use for both us and our clients. It’s so easy to book and personalize it to your needs and what you offer. Review collected by and hosted on G2.com.

We never had any issues and if we do, we reach out for help and get our problems solved quickly. Review collected by and hosted on G2.com.

Check Cherry centralizes our entire booking and client management workflow in one place, which has significantly streamlined our operations. The ability to create customized packages, automate quotes, contracts, and payments, and manage events through a clean dashboard saves us hours of manual work each week. The system is intuitive and easy to implement, allowing us to get up and running quickly without heavy onboarding. We also value the flexibility to tailor workflows for different event types (weddings, corporate, private events), which directly supports higher conversion rates and a more professional client experience. Review collected by and hosted on G2.com.

While Check Cherry is powerful, there are limitations around advanced customization and white-labeling—especially when managing multi-brand or partner (white-label) events. Pricing logic can also be restrictive when trying to handle different margins between what we charge partners vs. what they charge their clients. Additionally, deeper automation (conditional workflows, advanced upsells, or more granular integrations) requires workarounds rather than being native features. The mobile app is very useful but could use some improvement. Typing or modifying email messages within the app is painful. When you select text it is really hard to manage selection as it auto scrolls all the way down within the small window. Maybe it is an iphone issue, and not an app issue, not sure. Review collected by and hosted on G2.com.

I run an event rental business and use Check Cherry for my bookings, and it's been an amazing integration for us. It makes integrating and managing events wonderful. My customers can book on their own, and event planners can share referral links to earn commissions. It has great software that makes life easier, and I recommend it 100%. It is very user-friendly compared to others, and their support team works with you, answering messages quickly. If many users request a specific feature, they make it happen. It solves my booking needs, client management, and point-of-sale. I appreciate how user-friendly and easy it is to manage. The automations are valuable as clients can book and manage their bookings without my involvement, saving me a lot of time. The initial setup was very fast and easy, making the transition smooth. Review collected by and hosted on G2.com.

I would hope a security deposit feature could be added Review collected by and hosted on G2.com.

Hands down is the customer service! But what I like is that it reduces time with automations and minimizing how often I have to do the same tasks. Whenever something might not be working correctly or needs an update, their team is easy to approach. Review collected by and hosted on G2.com.

There really isn't anything I can think of that I dislike. If I ever have an issue, I go to their team to talk it over and either a new feature is released or they provide a work around based on what my needs are and the current functionality. Review collected by and hosted on G2.com.

I love that I can review everything regarding a booking. It has great auto functions, but yet it's manual enough for me to still be able to customize my operations. It keeps my team members organized and notifies them that they have event bookings gigs, which I love. It’s also a great way for me to remind myself if we’ve already booked or haven’t booked, helping ensure that we’re not undercharging or overcharging our clients. My team members have the booking gigs attached to their calendar so they receive text messages notifying them of events that they’ve been booked to work, which is one less task for me to handle. They receive auto text messages of their event, whether it’s a pre-event form, post-event form, or our manual. It just makes it really easy for our team to access. Review collected by and hosted on G2.com.

It’ll be nice to see more of a visual pipeline of our operations per event. Review collected by and hosted on G2.com.

I like Check Cherry's ease of use for both me and my clients, especially the client portals, which are absolutely amazing and include everything I need. These portals cut down drastically on the time I have to spend going back and forth with clients because they can book themselves and adjust their bookings right within their own portal. The initial setup was incredibly easy and very helpful, thanks to all of their videos, trainings, and the very fast replies from their customer support. Review collected by and hosted on G2.com.

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We use Check Cherry as the CRM for Tumbleweed Photo Booth, and overall it has been a great system for managing our business. It makes sending proposals, booking events, managing staff, and collecting payments very streamlined. I especially love how easy it is for clients to select add-ons during the booking process—it’s clean and user-friendly. Review collected by and hosted on G2.com.

My only drawback is with email integration. Since emails are sent from Check Cherry instead of my business email, they sometimes end up in clients’ spam folders. If that integration improves, this system would be nearly perfect. Review collected by and hosted on G2.com.

This was my first and only CRM that I used for my photo booth business. I love that it checks off all the things I need for my business from setting up packages, add-ons, building out quotes, adding package and quote alternatives, to be able to integrate other softwares that I need to run the business. Everything has been smooth sailing and the customer support is same day when I need it. Review collected by and hosted on G2.com.

I wish it did have an option for staff to request which bookings they want and payroll services Review collected by and hosted on G2.com.