The Key Components of a Successful Upsell Strategy! the easy way to increase bookings

Do you want more
Direct Bookings?

Are you ready to take your upsell strategy to the next level? 💰 Do you want to increase your revenue while also providing a top-notch guest experience? 🤔 Do you want to learn from a former Creative Director at Facebook and Twitter on how to upsell the right way? 🔥 Then you won’t want to miss this episode!

In our industry, upselling can be a powerful tool to increase revenue and enhance guest experience. By offering guests upsell options that add value to their stay, you can not only boost your profits but also create loyal customers who will return again and again. The key to successful upselling is to focus on adding value to the guest’s experience and not just trying to sell more products. However, upsells can be tricky… Focus on the incorrect value proposition, and you can end up losing trust or spamming guests. They can view your upsell attempts as nothing more than a money grab 😒, so how do you upsell the right way and boost your business’s customer lifetime value?

By understanding the needs and wants of your guests and offering them relevant, high-quality upsell options, you can create a win-win situation for both the guest and the property owner.

In this episode, we have the perfect guest for you. 🎤She has written, in both words and action, the Upselling Playbook and has worked as a creative director, at both Facebook, and Twitter. We are thrilled to have Annie Sloan, Co-Founder and CEO of The Host Co, as our guest. 🔥 We dive into the topic of upselling and how to do it the right way. We explore the essential elements of every upsell and how to determine what to upsell and what to avoid, and at what price. We also discuss various bundle-relevant products for short-term rentals, how to use upsells to provide value to your guests, and the opportunities for upselling in the electric vehicle industry. Additionally, Annie shares tips on creating short, engaging videos, popular upsell items for guests, and why guests will choose to purchase your product even though it might cost more.

When you cross-sell and upsell, you give yourself the ability to really examine your entire suite of services and products, to find a natural fit with your client. In this situation, I was able to bundle the design services I had with the printing services I could provide.

In this episode, we cover:

What are the essential components of successful upselling? 💰

How to determine the right upsell options to offer guests by understanding their needs and wants.

What are some opportunities for upselling in the electric vehicle industry? 💡

What are some of the popular upsell items for short-term rental guests?🤔

How to make short, engaging videos to pitch your products and services.📹

Common mistakes in upselling to avoid.❎

Annie Sloan is the Co-Founder and CEO of The Host Co., the company that enables short-term rental hosts to add instant amenities to short-term rentals – from massage and chef to in-home shopping and beyond.

As a former Creative Director at both Facebook and Twitter Annie built successful digital products as well as great stories. Her background includes leading projects for HGTV, Google, Microsoft, and Airbnb. A graduate of the USC Film School, Annie worked in film internationally and spent a cumulative four years on projects in Asia, Africa, and Europe. Through this, she developed both a global POV and a passion for supporting and strengthening small hospitality businesses through technology and creativity.

Listen to the episode to learn about unique upsell products, the upsell playbook, and why attending the Revenue Maximizer Mastermind Seminar is a must. Plus, find out how to pitch your products so that guests choose you.

📽 Watch the episode here
🎙 Listen to the episode here


Bart: Hello, everyone. Welcome back to another episode of the Accommodation Show. 

I’m very pumped this week because we’ve got the wonderful Annie Sloan on the show from The Host CO. The Host CO. Welcome to The Accommodation Show. 

Annie: Thank you. I’m very happy to be here.

Bart: We talked at the end of last year, about all things short-term rentals, amenities, upsells, making more money, and improving the guest experience. And what was lovely about our conversation was that I genuinely just wanted to talk to you for ages, but we didn’t have enough time, but this is the first time I’ve seen you since then. And I’m so excited to share you with our audience. Annie, I would love you to introduce yourself. Letting everybody know a bit about your background is quite interesting. What you do at The Host CO. and how you fell into this particular business?

Annie: Oh wow. Great to meet you all. I am the CEO and co-founder of The Host CO and we are a company that plugs in instant amenities to all types of short-term rentals. Things like massage chef charcuterie boards, even in Home Shopping. So that hosts have a new ancillary revenue stream. 

We’ll get into it briefly about my background. So I’ve been a short-term rental host for years prior to Airbnb’s existence I used to rent out my place on Craigslist, which I mean, that’s sketchy. I would ask for a licensed copy, and that’s it. And then I would leave town and go to like Guatemala or you know, Australia or something. And, you know, leave my apartment in San Francisco. No insurance right? As you do, but have gotten much more professional over the years with that. Prior to The Host CO, I was a creative director at Facebook. Prior to that, I was a Creative Director at Twitter. Don’t come at me, I don’t work for either company. So but throughout all of that time being a short-term rental host, and my co-founder runs a big property management company. We’ve just been talking about this huge gap, which is guests are asking questions, and we’re unable to solve so many of their problems right, essentially with amenities because it’s not automated. So that’s how we got to where we are today.

Bart: Yeah, amazing. Look at it. I love your background because I quite enjoy talking to kind of creative people, people that are thinking out of the box. And I think that within short-term rentals, you need a lot of that innovation. And I also think and this is really important is that a lot of the listeners of this accommodation professionals so people across the industry I mean, you know, it doesn’t matter if you’re running a campsite, if you’re you’re renting out what was gonna say tiny homes. If you’re in a massive hotel, you also need to be thinking about the same principles and this evolution in technology, as things are actually changing. And I love that you can bring a fresh angle to this and some of the problems that we’re facing, or it’s not even some of the problems but also creating solutions for our guests that we might not have thought of in the past. So it’s kind of bringing technology into the accommodation space. What are your kind of thoughts on that?

Annie: Really, that is so right on. I think that particularly through the pandemic. One thing that we’ve really seen a couple of megatrends here are one, obviously short-term rental has been booming and now hotels are back to booming as well to the short-term rental industry. Industry awareness was about 40% pre-COVID And that was 80%. So people who had never stayed in a short-term rental before now stayed in a short-term rental, and they have different expectations, staying in a short-term rental. The other thing that happened during the pandemic was on-demand services. So for example, I probably ordered groceries online, I don’t know twice, prior to the pandemic. Now I’m like, I don’t know Little Lord Fauntleroy. I’m like I’m not going to the grocery store, you know. But we’re also used to those on-demand services and having things available to us. And those two huge, huge trends essentially, coming together to short-term rental guests saying I want things and wow now I can get them via on-demand services or amenities available to me in the short-term rental. So right now, people are looking for that anyway.

Bart: Yeah. And there we go. So that’s the big reveal, folks. That’s what we’ll be talking about today is how, where the trends are going, and how to meet a changing consumer or guest’s expectation and bring that into your business. Because right now, we’re talking about more and more pressures, being on your business as there’s a more competitive landscape out there. So more and more people coming into the business, as folks are returning to the big urban setting. And going back to hotel so you’ve got even more competitors. And then lastly, of course, you’ve got all the economic pressures, which are going to put a lot of pressure on the business so when guests are turning up and this doesn’t matter if it’s a short-term rental but also hotels so older hotels, older motels, and we’re doing things that they used to you guys have to upgrade. I guarantee it otherwise you’re gonna really suffer because everyone else is upgrading around you. But once we’ve upgraded our place, and once we’ve made it all nice, we need to then deliver even more if we want to command a much higher price. So when we talk about guests getting things on demand, about amenities, about improving the guest’s experience, I would love to get your thoughts on this idea of the blend between an upsell versus adding value to a guest and then we’ll talk about later on server knows we’re talking about trends and things that you can do in your business. But I’d love to know your thoughts on that sort of juxtaposition.

Annie: Well, first I will say, we have about 15,000 hosts on our main social channels and we pull people a lot. And hosts in general run from anything upsell. Generally what I’ve found is that and we’ve discovered because most hosts think, “oh, I don’t want to be there I don’t want to have to say do you want this right and also never ever nickel and dime anybody. What we like to say is don’t ever sell anything to anyone that is under $20. Right? And if it is under $20, you should be providing that for free if you can, right so an example of that is give someone a six-pack of Lacroix right? Give them a sleep mask. 

Those are the kinds of things that they’re going to remember those lovely little things. But when every other guest says Do you have an extra phone charger and you know you’re not getting a phone charger pack if your guest uses it right, that is outside of the scope of what you can provide for free so always give what you can and there are so many little touches that don’t cost very much that you can get for free right, the note, the welcome basket. But in terms of upsells versus value add, make sure that essentially every upsell anything you can offer is always positioned as a completely as a value add. You are never selling anything to anyone and I think that is key in hotels in short-term rentals. It’s, hey, if you’re interested in a MidState clean because we see you’re staying for a long time, right or you showed up with seven kids do you need that? How about same-day laundry service right? 

Or a big holiday is coming up with flowers and chocolate, these can be at your door an hour after you arrive even so far as hey we know your booking in Austin during South by Southwest. Would you like two badges and would you like them delivered to your door right after you check in? All of those things. First of all, they’re going to be a value add. Even if people are paying for them. They’re still positioned as a value add. And they also give you a distinct edge in your property as well. So you can even write those into your listing, depending on if it’s you know if there’s a seasonality to it, or for example, here’s a great one because everyone remembers this one. The Superbowl is coming up. We have hosting Phoenix who are offering a charcuterie board in the shape of the team logo. And who wouldn’t order that right? And that’s probably going to cost you 200 bucks, right? 

But that’s going to be what you take on Instagram. Here’s another part of that upsell versus value add is what are people going to take an Instagram I don’t want to say just Instagram but take a photo op posted online so all of their friends, it’s not just Instagram wall anymore, or, the cowboy pool necessarily. It’s those additional things that you can bring in to make it something that they want to rebook or something that their friends will want to rebook.

Bart: Yeah, wow. So there are so many different ideas that are kind of coming to my mind based on what you’ve said already. And I think that’s the reason why I really enjoyed talking to you is because when you start to get a few ideas and your brain just starts going everywhere, I can do this and we can do that. So through this episode, folks, you’re gonna get so many different ideas of ways that you can implement technology into your business to provide a better guest experience and to do add-ons and that sort of thing. 

But I really want to push you a little bit harder on differentiating between what an add-on is and what’s to be kind of already expected as part of the property and I’m going to give you an example to really make your life a bit difficult. Hopefully, I had a client of mine reach out to me and said, “Hey, Bart, over the Christmas period, we’ve been inundated with EVs, so electric vehicles, and they all expect to charge for free to charge their cars for free.” And there’s this kind of debate of well, how much does it cost? So charging an Eevee overnight is anywhere between sort of $5 to $10, roughly, depending on how long and that sort of thing if you’re not using a fast charger. So how do we as hosts, as hoteliers? How do we figure out, is there a formula that we can use? No Well, that’s that we can charge as an add-on that we can’t how do we how do we figure out a good baseline to work from

Annie: I understand people saying, oh, what should be included? Right? I think the first thing is to bundle things. If you make sure they’re not a $5 item again, people in general. Oh, $5 for parking. When you talk about where we are in Joshua Tree in Palm Springs, everyone charges for pool heating. That’s like 200 bucks for a week. Right? And it has just become really normal because it’s expensive, right? People don’t know that. It was expensive. So putting that up front, offering something like unlimited charging this much. I mean, there’s it’s interesting how you would control that right? But I’d say bundling in general would be it or just making it very, very clear. Obviously in your notes, what is included and not included? That is something that’s the cardinal sin, right? is putting something in your listing and then charging for it. Right. That’s like saying, Oh, we have a llama farm and then you know, they arrive and you say great, it’s 20 bucks to see the llamas. 

You know, you never do that right. The other thing is don’t mention it and then after booking again, position things as an offer. If that is something that it is really adding up and it is really cutting into your bottom line to do Evie charging right after they book. say “here are the amenities available to you.” And maybe include that as an amenity. Just even so it’s socialized. Right, right after booking, so it’s socialized, I think is key to that.

Bart: Yeah, love it. I think there are some great tips in there. And I will the one that really strikes me is nickel and diming. So then if it’s a low-value cost to your business, you know some of it you’re just gonna have to wear or include in the price of the actual booking. Because otherwise, people will not feel great about booking with you, you’re gonna make them feel crap before they’ve even started. And then you’re probably going to try to add on other things and do that and they’re gonna be like off yeah, you’re charging $5 or $10 for the charging for car charging, what else is it gonna be? 

So I love that and then so let’s go back and have a quick talk about guests’ expectations and things changing within the marketplace and where we see that going. So, last year, if you’re in a short-term rental cars kind of money for jam, people would just turn up and they’re kind of clamoring over each other everyone was putting up their prices this year, it’s predicted to be a lot different, it’s gonna be a lot tougher. So, therefore, we need to improve our service offering. The way I see it is that we need to not only offer a great place to say we also need to ensure that the experience is consistent, that it’s exceptional, and that it meets our customer’s needs and to meet our customer’s needs. We need to understand our customers. So that’s customer avatar, which we’ll come back to but when we’re offering these upsells and add-ons and that sort of thing, where do you see that fitting into this puzzle?

Annie: In a couple of places, I completely agree we were in an area that was for my own rentals, super high demand. And then just in general, super low predictability. Right. You don’t know what you’re actually going to get or how good it’s going to be. So making sure you’re very consistent. And then mentioning so in terms of, again, add-ons and upsells either including that in your rental so this is another thing that that we are seeing is spa weekend, and everything is included right in that and you can charge a whole lot more for that. If you put that together yourself or you figure out the bundle that you need. That includes massage therapy for two it includes flowers or what have you, right and you can set that up as one package. Or directly after booking you can always say we have additional items available, including in your listing things that are going to catch people’s attention things that are you know the whole journey that you’re sending them on you’ll arrive and you’ll you know we’ve talked about this you’ll arrive and sit by the sea and then you’ll optionally include bohemian picnic for four in an inflatable bubble on the beach. Just again, snap positioning just let us know if you’d like that while you’re here. 

I don’t know how Bochy dinner for 10 is available. Those are the things that mention but making sure that it’s not included. It’s available or if you’d like this right. If you can include that in your listing and people go you know, their ears perk up because they’ve been reading other listings where they don’t have any of that available right. And then directly after booking, just an automated and what our service does, it’s an automated digital storefront where you can essentially offer any of these services and then it connects to your vendor or our vendor and schedules everything and pays them out. So you’re you know, you’re not doing much, which is great.

But sending that right after booking and people might not say. ” oh, I want that hibachi dinner for 10” now, but it’s socialized. So as they get closer or as they start really planning on Okay, where are we going to what are we going to do where are we going to eat? Well, you know, it’d be great one night is this is that in the other? Right? So making sure right after that booking adrenaline, oh my gosh, when planning and then what we see host doing some of our top sellers. They’re sending up they do quite a bit of direct booking, they’ll send an email 30 days before they arrive, and they will include an image of their store so you can see because nobody reads anymore. Sad. I mean, we’re all looking at a screen. So seeing those different things that are available is a real driver of people. Oh, I want that, that, and that.

Bart: Yeah, yeah. I love that. And I think that one of the formats has come out really strongly this year. And I think that this is a good tip for everyone, to use video a lot more as well. So if you can create a little video, it doesn’t have to be well produced. All you have to do is and there was a coach that told me this like I’m fired. It’s so easy. Why are you putting so much effort into it? He said, Look, get your camera filming your face saying I’m going to show you blah, blah, blah, stop, flip the camera show whatever it is that you’re trying to do, just as if you’re reading it, have a look at this, and then put the camera back. Isn’t that amazing? And then you stick it all together using Instagram or an app. It takes you literally a few minutes and all of a sudden you have quite a piece of content that is quite engaging, And that people really live and you’re building a bit of personality too. So that’s, that’s what I’m doing is just for my clients. 

What’s fascinating about this conversation that we’re having is that this idea isn’t new, and it’s been something that I’ve been thinking about for a year and a half. I did a course on this maybe a year and a half ago two years ago because we’re trying to find ways to get more margin out of the property but also really important to improve the guest’s experience. One of the things that you’ve kind of started to lean into is rather than just talking about upsells and selling and selling and giving people this and that and they have to spend more money. There’s a whole converse of that, which is certainly an experience so the experience can be and one of the ones I love is you’re on the property, a helicopter will come and pick you up and then take you to a local winery for some wine sample. Then you’ll have some wonderful lunch, and then you’ll get helicoptered back, and then when you get back to the room, it’s all set up nice and you’ve got the gowns, out flowers, and whatever else right so the ultimate romance package, and the margin that you make on that is just ridiculous. 

Because the price doesn’t matter anymore, right? It doesn’t matter. It’s the experience that you’re getting. And then from a host perspective to settle this up, it is not incredibly expensive if you price it correctly. So this more experienced type of economy and that sort of thing. I think it’s really important to understand and understanding what we have to offer and where the market is going. So I don’t recommend that everyone starts to do these kinds of experiences, but there will be experiences that fit your guest’s avatar. Are you seeing any trends? What are your thoughts?

Annie: Oh my gosh, well, I think you are so right on that it is really specific to the rental and obviously what you can put together or put together with vendors. We see people who are literally selling North Carolina’s state-shaped Christmas ornaments all year long and that’s all they sell. Right? But they’re adding, I don’t know 30 bucks 30 to 60 because people might have I don’t know why they do. But that’s $60 per booking it starts to add up right and then we see people who are doing quite a bit of higher priced items. 

I would recommend doing things that are much you’re gonna get a higher margin on them but it’s just fascinating what works for each location. A personal chef is absolutely huge. Anything let’s say laundry, even if you have laundry, having someone fold it and put it away. It feels like a vacation. Right? If you look at the pie graph of what full-service hotels offer. Full-service hotels make roughly 30% of all of their revenue on upsells. And if you look at short-term rentals, there’s it’s you know almost nothing or nothing right? I’m in full-service hotels, the largest category is food and beverage by far and that’s because they have bars you know, we all love those right? But food and Bev if you just map to that is going to be your best even if it’s you know $400 In in snacks dropped off. I do that with my girlfriends for the weekend.

The next category is wellness. And that is something that I’ve been talking about trends even, I don’t know 10-15 years ago that that probably was alterations rather than wellness but wellness is massive. And that’s what people want to do on their weekends. One of our biggest sellers is massage, Reiki sound bath facial meditation sessions with a professional coach, private yoga, and again, I mean these are often I would say they’re booked more by female guests than male guests but it really depends. IV hydration which is where a nurse I don’t know even know if you do this out of the states or even out in California.

Bart: The first I need the first time I saw it was in Vegas when I was over there and I was so tempted. I was like in the morning I woke up I was like, Okay, I’ve had a Vegas night and I’m like God, I understand that.

Annie: And it is expensive but again, anything involving wellness or hangover those are absolutely huge. And then certainly alterations which if you have a property management software, most of them can do late-check out early check-in mid stay clean, but you can go far beyond that. We see quite a bit of pool heating, and access to different spaces that you couldn’t ask that we’re not again on your write-up. So you’re not saying you know, again, you have access to everything and you don’t. We’re also seeing a personal trainer, or like coming someone coming in to do a person and those are more for MidState clean, and then you get down to those smaller spice slices. Rentals things like bikes, kayaks, we see that and then just goes down from there but I would always say focus on that food and Bev focus on wellness and then some unique experiences if you can put in those as well.

Bart: Yeah, look, I think some great advice I think the one break that I want to explain to everyone is the bridge of why would a guest choose to purchase whatever through you even though it might be more expensive than if you were to Google it. And it’s kind of it’s a really interesting one because for this kind of stuff, you think, well you know what, any? I’m smart enough. I’m gonna jump on Google. And I’m just gonna Google it and find the best restaurant or private chef, or the best spa. I don’t want some crappy spa thing. I want the one that’s rated five stars from XYZ. And the key to this whole equation is that you as a host, already have a relationship with a person. Hopefully, you’ve built a lot of trust already, through your five-star ratings through all your reviews, through what your property is like when they get there through how it smells when they get there through the music that you’re playing through the Alexa when they get there. 

So you’ve already built all this trust, and the way that you pitch these products, trust me I’ve done all the work for you and I’ve found the best way to create a great experience for you. And that is exactly what a brilliant concierge would do. You go down and they go trust me. I’ll look after you because what happens if the consumer is less than one they’re probably not going to get their tips and two, you can go back to them and look them in their face and say your recommendations were rubbish. So but now we do that with reviews. So that is the power of this and that is how you leverage this it’s not about you just putting stuff together and then, you know, giving you an option of 20 different things. It’s about finding the best tour of the local city that’s put together by Brad who’s been doing it for 20 years and he’s definitely the best I’ve got a great relationship and health Brad will look after you because he knows me.

Annie: Yeah, I would say also, one is trust twits time. I have been to places where So Joshua Tree again Instacart, doesn’t deliver, DoorDash doesn’t deliver, and caviar doesn’t deliver because you’re out there. There’s only one service and do you want your guests spending, you know, two hours on Yelp trying to figure that out and then having a poor experience you’re saying just operationally Let me save you time. You already are trusting in me. And then also, you know one or two of the more things that you know that they will book but what is also unique to you or your listing. We have property managers who hooked up mobile tattoo artists for your bachelor party. Who’ve hooked up Faerber saddlebags full of beer and you have to chase them down right? Someone who’s hooked up tintype photography because it’s all that LA hipsters, you know, coming out to the desert. Those are unique to you and unique to your property. We also have someone who works at a wine shop and they said my friend is a small Yan will come for four hours and do a wine tasting. 

So what are those unique things that you just can’t find anywhere? And then on top of that, what I think is the key is what are your guests already asking for. And particularly if you have a property manager and you’re not doing it yourself, they’re probably not telling you the things that your guests ask for that they can’t fulfill. If that’s I don’t know firewood, or that’s where can we find a mobile tattoo artist, your guests are going to start asking generally the same things about your local area. Oh, we want this just like everybody else had. Right. So just listening first and getting that customer avatar that you’re talking about, that guest avatar meeting what we like to say is just like a concierge can do, meet their need right before they even ask for it. So halfway through their stay. Hope you’re having a great time. Let us know if you need a mid-stay clean if you need laundry if you want a private chat. Oh, I was just thinking about all those things. So you can really map out the guest needs along the lifecycle of their stay and then meet them there and say I have a solution before you’ve asked me for it.

Bart: Annie I like to keep our episodes at The Accommodations Show relatively short. I try to keep them within that sort of half an hour window because I think before we started you said I could talk about this for 12 hours and you know what, I could probably talk about it with you for another couple of days and get pretty deep on all the different things and different ways to plug everything together. A few things are gonna say So folks, if you aren’t listening, one of the most important things that you can do is you can subscribe to the channel. We’re looking to grow the subscriber base this year into the 1000s one so that we can monetize it and get a little bit of money back but more so so that we can provide more value in keeping on doing what I’m doing and getting in front of these amazing industry leaders, these innovators these creators and getting them and convincing them to come on and share their time and their experience with you. 

So please subscribe. Leave your comments below. We’d love to know what kind of amenities you are offering and what kind of upsells you are offering and whether you’ve thought about it at all. The last thing is I’m gonna do a little pitch for myself. Annie, tell people how they can get in touch with you and whether you’ve got any special deals for our listeners.

Annie: Yes. So you can find us at, you can sign up to get the playbook on how to implement all amenities easily. Again, this would have been done 10 years ago if it wasn’t a pain in the bleep, you know insert whatever now you want so that’s the important thing is how you can add this very quickly. That’s and we do have a promo code. Use code I have to look it up. TAS and you will get $50 back from the first item you sell in your store no matter what that is.

Bart: Yeah, that’s amazing. Thank you so much for that offer and I know it makes a difference. The one thing that I really want to stress to everybody, particularly when things are tough. Profitability is of course important in your business, but making an exceptional guest experience and making sure you focus on an experience that is what will give longevity in your business is making sure that you’re doing stuff that other people are not. The one last little plug that I’m going to do is there I am actually doing a course called the revenue Maximizer Mastermind, where we will be talking all things upsells packages, with guys and instructions on how to figure out your guest avatar. How to figure out your relationships and your partnerships because there are huge opportunities for cross-promotion and social media and that sort of stuff. And then lastly, how to put together the packages and make them absolutely exceptional. That’s something that we’ll be doing and the links will be in the show notes as well. Any Sloan you are exceptional. I hope to see you too. And I hope that we can do lots of work together. You’re amazing. Thank you so much.

Annie: Thank you This was so darn fun.

Bart: Look, I think I’ll be coming over this soon and we can sit down and have a few beers and wines and 

Thank you so much for listening to the show. You can find us at where you can find all the show notes and links to the resources we talked about. I really do appreciate you listening. And if you’d like to support the show, please subscribe. Leave a comment, and share it with others.

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