Surviving the Holiday Rush

The holiday season is here and so are packed weekends, price pressure, and endless client emails. Join us for Check Cherry Live: Surviving the Holidays, where Judd and Matt will show you how to simplify your workflow, prevent overbooking, and maximize profits when demand is highest.

You’ll learn how to:
✅ Use Flex Pricing and surcharges to boost revenue on peak dates
✅ Set booking caps and blackout dates to avoid chaos
✅ Organize staff and manage availability like a pro
✅ Save time with the Client Portal
✅ Automatically reach back out to this year’s clients for next year’s bookings

Perfect for those who have a busy holiday season.

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0:00 Tonight we're going to do something a little different. Uh kind of it's Chick Cherry Live, surviving the holidays, you know, and we're going to talk about some of the things that we see our customers use around the holiday season. Um really it's interesting because we see on the platform uh a lot of revenue connected collected leading up to Christmas Day and then it just kind of like our

0:24 lowest week of revenue collected is that Christmas week. So, it's like the highest and the lowest are right next to each other each year. And, uh, from what we see, a lot of that has to do with, uh, photo booth customers doing corporate, uh, bookings in December. Um, obviously there's weeks or there's bookings throughout the week and so on. And so, uh, we just wanted to kind of share

0:48 some of the things that you could, uh, set up in your account. Um, give you guys an opportunity to share tips, uh, that you're doing, um, that type of thing. So, I thought uh Matt would drive as usual. We kind of show off some features and just have a discussion. We like to keep these things pretty casual. So, if you want to hop in and chat, raise your hand. Um you can also leave a

1:07 comment. I'll monitor that as well. U but these are just basically tips and tricks to help you during the busy rush make the most money, stay organized, you know, that type of thing. So, um, Matt, maybe you could share your screen, hop into the one of the demo accounts, and I'm looking for the chat window. There it is. Um, and again, we like to keep it casual, so if you have questions,

1:33 you know, feel free to u hop in there. But, um, you know, again, it's about making money, staying organizing, staying organized, and just stressing less. Um, so I think that um, probably a good place to start in my mind is with flex pricing and holiday search charges and the stuff we see our customers do. Um, and the reason you do this simply put is you know you're going to

2:00 get booked in December and um, you know, if you're offering online booking, you're sending proposals, you can configure flex pricing and check cherry to automatically add a sir charge uh, to a booking. So maybe it's like 25%, you know, on top of my regular package prices or maybe it's $150 search charge, that type of thing. Um, yeah. So Yep. Go ahead. Yeah. So with with the uh the flex pricing

2:29 um you know you'll find that along with a lot of other settings under the manage dropdown. Um so if you go to manage flex pricing you can set that up and the way flex pricing works is that is that um basically it modifies any any pricing you already have in the system. So, if you've got a package that you charge 500 bucks for, you could um you know add a search charge or

2:50 a discount to that. And with flex pricing, it'll automatically be be applied and only if those uh certain conditions are met. Um so, if we wanted to have a uh Decemberwide um special, you know, December 2025 pricing, uh you know, it probably makes sense to do that as a percentage. And so we might do a, you know, whatever, you know, 10% search charge on that. And you can also come in

3:17 and limit that to certain packages as well. So, you know, it's real common we'll see like, oh, I just want this to apply to, you know, to my photo booth or to certain booths or things like that. Um, less common, but also sometimes useful, you can also limit it to certain add-ons or even backdrops if you want to. Um but probably most common is is limiting it to only certain packages.

3:39 And the next section you'll see is um what does that search charge apply to? Um and basically what that lets you do is you know most commonly this is either going to be you know like hey if if somebody chooses a package and then a bunch of add-ons you know does that 10% search charge apply to the full amount or just the um just the specific package. Um so with this setting you can

4:01 kind of control that. And then for um for these purposes, you know, for for this uh um you know, December, we want to look for bookings that start on a certain date. So, we'll go ahead and say from December 1st to December 31st. Um and then that'll automatically apply. Um lots of other settings as well, but but that's kind of the main one. Um main thing I would, you know, just double check, you

4:28 know, we also do support based on when something is booked. Um, but if you're trying to do uh holiday pricing, you'd want to use the start time, you know, the start date of the event. Um, and as usual, chat with us anytime you have questions on that, flex pricing is used for a lot more than just this use case. There's a lot of different ways uh you can add uh search charges and

4:47 discounts with Check Cherry and and we think flex pricing and one of the reasons we came up with it um is that we we saw customers would want to have special like this these are my holiday packages you know type stuff and it just becomes unwieldy um and not a great solution for something like Check Cherry um where you have all your packages in one place. Uh we do have some customers that do

5:09 that, but we think the flex pricing um and putting them under maybe a corporate package group um in your packages is and then adding flex pricing is absolutely the way to go and it works really well. It's also worth noting it'll show up as a separate line item on the invoice so the customer will know uh why they're getting charged more. So if they come back and book you, they're going to know the

5:30 prices that they saw um on your website initially or that type of thing. Um, but yeah, I think it's absolutely and kind of along these lines, another thing we see a lot around this time of year is that people want to do like maybe like a Black Friday special or some kind of a discount. Um, and again, you can do that one of two ways. You can make it something that automatically

5:52 gets applied. you know, anybody that books you on, you know, the Friday after Thanksgiving, you could come in and say, you know, based on uh whatever day that is, you know, either that specific day or that whole weekend, you could say, "Hey, you know, those people get a $100 discount." Um, and that'll get applied automatically. Or you can make it more of a code that, you know, that

6:14 you give to people where they have to type it in and um, you know, manually enter it. And that can be kind of nice from um you know if you want to send it out via email or on social media or things like that. Um sometimes those codes are nice. And again what you can do is say um under the discount codes based on the book date you could set it to you know the 28th and you know maybe

6:38 a couple other days too. So um so yeah that's another thing that we see a lot this time of year. Another thing that's popular is people will do a search charge uh which typically is going to be more than just your entire December for New Year's Eve weekend. And so New Year's Eve weekend falls on different time periods. I don't know if you want to go to the calendar picker and see kind

6:57 of where that falls this year, but um and if you know it is important that um flex multiple flex pricing rules can apply. So something to be aware of um you know but New Year's Eve you know that type of that night um can be very popular. where we've seen customers 3x their prices, 2x them, that type of thing. Obviously, uh you're probably, you know, going to pay staff more, too, I think,

7:21 is is uh common. And anybody has if anybody has, you know, anything to share on how they pay staff around the holidays, I'd be curious uh to know how that goes. Um you know, what you guys are doing. But that's a great way to still maintain your profitability, take care of your people, and uh get those bookings. Awesome. Yeah. And then uh I suppose also worth noting, not everybody wants to

7:45 work New Year's Eve, Matt. So we also do that. And so another thing that's important to know is you can set blockout dates in check. And so you can basically say, hey, we're not going to take any bookings um during a certain period. Um you can block off all of your uh availability basically. And so that can be very helpful. Yep. I'll let you take it away. Yeah. So, if you go to the calendar,

8:12 um that's the easiest place I think to create the blackout dates and um go to sales calendar, click add new and add a blockout date. And so once you select that, you know, that can just be a simple date if you want, you know, if you're going to be out of town traveling for for uh Thanksgiving. Um I don't even know when Thanksgiving is this this month, but um you can put in those dates

8:35 to block it off. Um, and you can make that all day or just part of the day if you need to. Um, and you can say, you know, travel. Uh, this is this reason is just for you. This won't show up to the clients or anything like that. And then you can also block out just certain packages. You know, maybe you have staff that can handle photo booth, but you know, for other things, you know,

8:55 for weddings or for, you know, you probably won't be doing a wedding then, but for certain services, you might not want to take. So you can u by default block out everything but you can also just block out certain things if you prefer. Yeah. And I think um you know another thing that can happen in the holidays is you'll get uh more last minute bookings. And so a couple of things to think

9:18 about. One is um there are some settings if you're offering online booking as to how soon you're willing to offer how much lead time you need. So just something to be aware of. Um and then also you can searchcharge for last minute bookings uh as well. So those are two two options um you know to go into I think in yeah another thing that comes up a lot with you know this time of year

9:44 is you know obviously you might be out of town or you might be traveling you might not want to take bookings you can also um that's going to come up a lot with your staff as well and so your staff have the ability within the app within their account to set days off. Um, you can even make it so that they have to, you know, basically submit that and you can improve it. But within the calendar, you

10:07 can toggle on and off um, all of your staff off days. And, you know, a lot of times staff don't go through the app or they, you know, maybe they just send you a text or things like that. You can also record that yourself so that you have um, you know, just enter the staff member and the dates and reasons to block off um, to block them off as well. So, um, it makes it really easy to see

10:30 who's available, who's not, um, and make sure that you're able to, uh, you know, you have sufficient, uh, availability to cover your different days. Yeah. And I suppose just for, you know, if anybody's new, you know, just letting showing them how you assign a staff member might be helpful. If anybody's new to Check Cherry. Um, yeah. So, if we go to, you know, any any bookings that come in,

10:53 you know, when somebody comes in through the online booking, they accept a proposal, they're going to have a booking with you, and you can see all of your bookings, you know, lots of places, but under sales bookings. And if we go to one of these bookings, um, we're going to have a section called staff here. And so, if I click assign staff, I can see who's available,

11:14 you know, scroll through. If they're unavailable, it'll show it. So, I can see that right there and assign them. Um, I can even give them a role if needed. And when I click that assign button, um, by default, you know, unless you've set something else up, by default, they're going to get an email letting them know that they've been assigned to that event. So, that's going to have the, you

11:34 know, the details and then if they click through on the link, um, that's going to, you know, depending on what you give them access to, they'll be able to see things like the date, the time, um, you know, package, all that type of stuff, where to be, um, and things like that. So yeah, I think that's helpful. Um, and so maybe just touching on those availability settings. Um,

11:54 yeah, there will be more bookings. Uh, so you want to just double check your availability settings so that you're not uh over booked. Um, and so that'll be helpful, too. Yeah. So under uh manage business settings and availability, uh, that's where you can come to set your availability settings. And so, you know, if you're real small operation, you know, that can just be as simple as saying, "Hey,

12:19 businesswide, we can only take one booking at a time." Um, you know, and and when we say one one at a time, that could mean, you know, one per day, or you could, you know, maybe stack them if if one's in the morning and one's in the evening. Um, you could also bump that up to two. You know, maybe you've got two booths and you think you can be in two, you know, handle two events a

12:39 day. Um or you can take that out and not have a limit at all. Um and then if you scroll down to your packages, you can come in and set rules based on that as well. So um you know, if you have one 360 booth and uh you know, two two of some other booth, you can set those limits as well. And basically the way availability in Check Cherry works is that we'll go through all of the

13:05 different rules and see if there's anything that prevents somebody from uh from booking you. So, you know, if if you've got a businesswide rule of one, you don't need to come through and set one on every single package. You know, it's kind of there's no way for anybody to book more than one. So, it doesn't, you know, so it's pretty simple. Um but, you know, it also wouldn't hurt anything

13:27 if you did. Now, so, oh, go ahead. Yeah. And then I was also going to point out the the lead time. Uh, so this lead time setting is important, too. You know, if you set this to none, you know, somebody can book you for, you know, 30 minutes from now. And, you know, that's probably not not what you want in most industries, right? Um, so typically we'll see that, you know,

13:51 at least a day. You know, some people like to push it out a week. Some people push it out further, but you know, generally you'll want to set that at least uh, you know, a day or it's worth noting if you're offering online booking and you have that setting and they're within the time frame, you'll still get a lead, right? So, you'll still see things. And so, another thing that we'll see

14:10 is people will get leads and then they'll find maybe uh somebody else to handle the booking that's outside of their organization, kind of a white label, so to speak. And maybe it's worth showing them on a proposal how you can kind of override uh the availability settings to say, "No, no, no. I actually do want to do this. Even though I'm over my caps, I have somebody that's going to

14:31 do it." It's probably worth mentioning that, too. Yeah. So, say somebody calls you up. They're like, "Hey, I've got, you know, I need a 360 booth." Uh, let's see here. Got weird names on this one. um I need a booth, you know, for like tomorrow. Um if you click this reserve date checkbox when you're creating the proposal, what that's going to do is that's going to hold the date for them. And so

15:01 we'll basically, you know, will will prevent that from being um you know, basically that that kind of overrides your availability settings. Uh after you've created a proposal, you can also change that as well. So, you know, with this proposal, this one says proposal date reserved. And again, that just means that I'm holding this date for them. Um, I'm not going to let, you know, if

15:25 even if somebody else comes in and books, it's not going to make it so that that this is unavailable. You can also treat your proposals as date open. And with date open, it's kind of more like, you know, a little more like online booking where if you know, maybe you send them that proposal, the day was available, and then somebody else comes in and books you, um, you know, if that causes

15:49 it to become unavailable, we're not going to let them book. So, uh, it's worth kind of considering like do you want to, you know, in general, I would say most people typically use one or the other. uh you know and so it's kind of worth considering like do you generally when you send a proposal are you holding that date for them or are you uh kind of treating it as first come first serve. The

16:10 other thing when you create a proposal uh we have this proposal valid through setting and this is a a nice way to make proposals expire. So you know it's great if you want to hold a a proposal for somebody but you probably don't want to hold that for them for six months. So setting a proposal expiration is real helpful for that. And you can set a default of say 7 days out. Um you can say

16:35 hey anything um you know for all of my proposals I want to default something. That's why this is currently prefilling. Uh but you can also override that as well. You know if they're like hey I'll get back to you by Friday. You know maybe you set that expiration on Saturday so that they don't um they don't get over or that right you know you're not holding that forever especially

16:55 this time of the year. So, I like it. Um, and so, yeah, we covered blackout dates, um, time off. Um, yeah, and I think, you know, again, I I just would recommend not having separate holiday packages. It's going to keep your reporting uh, cleaner and simpler and using the flex pricing. um you know they think that's really the way to go in terms of being able to just

17:23 manage the business and the reporting and also maximize the revenue. Um you can always include certain things you know to the packages after the fact you know all that stuff. It's yeah um and so kind of define that a little bit. So under under managed packages sometimes we do see people set up you know they have their kind of their normal packages you know their basic classic

17:44 and premium and sometimes people will have just a holiday package with with that special pricing and you can do it. Um, but as Jud mentioned, kind of the disadvantage by having a separate package or se separate pricing like that, um, you know, when you kind of look at your stats of how many how many premium packages did I book all year kind of gets thrown off because you've got something

18:06 else there that you know that doesn't fit that pattern. So, and then um, yeah, and again the bookings I see just tons in the photo booth world, just tons of bookings in December. So, uh, always makes me happy, you know, to see that. Um, probably not worth discounting a lot. Um, great to to keep earning and so on. Does anybody have any questions or comments about how their

18:30 holiday bookings are looking? Um, is it, you know, are you are you happy with the holiday so far? Um, I can hop over one one thing I can kind of show off is um just kind of what what the numbers do look like throughout the year. So, uh, we've got these internal stats that we keep of, you know, when when do bookings happen. Um, you know, and then when is revenue collected and the,

18:59 um, you know, the the revenue collected is going to be a little smoother because, you know, somebody's booking you maybe a month out, uh, maybe a couple months out. They're going to pay that deposit and then they're going to come in and pay the the revenue, you know, the rest of it at the end. But the bookings happening is going to be gets a little bit

19:17 more spiky. And so you can kind of see, you know, um so far what we're seeing, you know, this year is is up over last year in in terms, you know, um of bookings happening. Um but the the pattern is pretty much the same from year to year, you know, depending on when holidays fall and things like that. And you know, this is this is the big spike last year, you know,

19:38 December 9th to 15th. Um, you know, I'm not sure which which weekend that'll correspond to this year, but uh the spike is just, you know, it's huge. It's not not much in, you know, the first week uh or that last week in November. Big spike here goes even higher. Um, you know, drops a little bit and then the slowest week of the year is the week after. So, we generally see

20:02 the the busiest to the slowest um, you know, happen within a week or two of each other. Yeah, love it. And of course with that, you know, we'll see the the bookings come in. You know, people are booking out a ways before that, though. So, you know, all those bookings that are going to happen in December, they're they're getting booked now. So, now's the time to be marketing

20:25 if you know, make sure you're you're out there. Um you know, any specials you have, any you know, have your pricing in order, you know, that's all all coming through now. So, right. Love it.

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