Five Questions to Ask Whoever Runs Your Guest Marketing
By Eli Pritykin, founder of HomeRunner.
Your website takes the reservation. A different system talks to the guest before and after the stay, and most operators have never looked at it as hard as they look at their website.
These are the five questions I would ask whoever runs that system. SendSquared is the worked example throughout, because we built an integration with them and I know how they answer each one. Every question comes with a check you can run in about ten minutes on whatever tool you use today.
1. Does it read reservations from your PMS, or do you upload lists?
A guest list exported on Monday is wrong by Wednesday. Someone cancels, three new bookings come in, and the pre-arrival text goes to a family that is no longer coming. Guest marketing is only as good as the reservation data under it, and a spreadsheet upload is a photo of that data taken last week.
The ten-minute check. Make a test reservation in your PMS. Time how long it takes to show up in your marketing tool with the right guest, home and dates, without anyone exporting a file. Then cancel it and watch what the tool does.
How SendSquared answers it. Their vacation rental CRM page says it directly: “Real-time PMS synchronization keeps guest profiles, reservation data, and property information current without manual imports.” Past reservations are imported during onboarding, so the guest history is there on the first day.
Live reservation data is also what makes small, specific sends possible. Their product booklet does the arithmetic from their own campaign data: one email to 50,000 people at a 0.07% conversion rate produces 35 reservations, and ten segmented emails to 5,000 people each at 0.37% produce 185. The segments they rate highest all come out of the PMS: locals-only offers, loyal guests by number of stays, lifetime spend, first-time guests, and guests to win back from the OTAs.
2. When a guest texts, then emails, then messages on Airbnb, is that one conversation or three?
The guest thinks they are talking to one company. If your team sees three inboxes, the person who picks up the third message has no idea what was promised in the first two. SendSquared’s site sums up the cost in one question: “Who promised late checkout?”
The ten-minute check. Text your business number from your own phone. Then send an email from the address on the same guest profile. Open whatever your team works from and see whether those two messages sit in one thread under one guest, next to the reservation.
How SendSquared answers it. “The Unified Inbox threads every channel together per contact, linked to their CRM profile and reservation data.” That covers SMS, WhatsApp, email and Airbnb messages. The screenshot in their booklet shows the layout: the conversation in the middle, the team member it is assigned to, and the guest’s reservation on the right with the dates, the unit and the booking value.
3. When a guest abandons checkout, does anything pick up the cart, and does it stop when they book?
This is the one I can speak to firsthand, because HomeRunner built the website half of it. A HomeRunner site with the Conversion Kit add-on sends an abandoned cart to SendSquared with the guest’s email, the home, the dates and the total. You can see every field that is sent. SendSquared runs the recovery sequence by email and text. When the guest books, our side tells SendSquared to close the cart, and SendSquared stops the journey on its own as well.
Ask about the stopping part as carefully as the sending part. A reminder to finish booking that lands after the guest has already paid costs you more than sending nothing.
The ten-minute check. Abandon your own checkout with a test email address. Write down what arrives and when. Then go back, complete the booking, and count how many reminders still show up.
How SendSquared answers it. Their revenue recovery page describes automated email and SMS sequences that start when a booking cart is abandoned, with recovered orders and recovered revenue tracked. Their HomeRunner integration page breaks the numbers down by channel.
4. Can it tell you what a campaign earned in bookings?
Opens and clicks are easy to report. They do not tell you whether the send paid for itself. The number an operator needs is booked revenue from real reservations tied to a specific send. The second number worth asking for is what each guest has been worth across every stay, because it changes who gets your attention. An anniversary note to a family that has booked four summers in a row deserves more care than a blast to the whole list.
The ten-minute check. Pick your biggest send from last month and ask for one figure: revenue from reservations that came out of it. Then ask who your ten most valuable guests are. If either answer needs a spreadsheet, the tool does not know your guests’ reservations.
How SendSquared answers it. On their marketing page: “Revenue attribution connects every send to actual bookings so you know exactly what’s working.” Their lifetime value page describes total revenue per contact across every reservation, read from the PMS in real time.
5. Can your own AI tools work from the same guest record?
Operators are already asking Claude and ChatGPT questions about their business. Without the guest record, the answers are generic. With it, an assistant can find the guests worth writing to and draft the message with their stay history in hand.
The ten-minute check. Ask your assistant a question about real guests, something like “which of last July’s guests have not rebooked?” If the first step is exporting a file, the record is closed to your tools.
How SendSquared answers it. They run an MCP server, the standard way to connect an AI assistant to a system. In their words it gives Claude, ChatGPT or a custom agent “read and write access to the same guest records your team sees, with tenant-scoped tokens and a full audit trail.” Their product booklet gives an example close to the check above: find the repeat guests from last summer who have not rebooked.
What to do with the answers
If the tool you use today passes all five, keep it. You are in better shape than most, and your next gains are probably on the website side.
If it does not, the path in SendSquared’s booklet is the one I would follow. They call it “From OTA guest to direct guest,” with the line “Pay the commission once. Never again.” The first stay comes through an OTA, with a masked email and no relationship. A WiFi sign-in and a post-stay survey build one profile with a real email address. The second stay is booked direct, with no commission.
The booklet also maps the touches between those two stays: a review request a day after checkout, a direct-rate code after a week, a seasonal offer at three months, and an anniversary note at a year. Their remarketing page covers how the real address gets captured. Every one of those messages ends in a link, and that link landing on your own website is where a site like ours comes in.
SendSquared is who I would call first. You can book a demo, or take them up on the free site read: a person on their team runs a booking through your website on a phone and writes up where the path to a confirmed reservation breaks. They write it up whether or not you ever buy anything from them.
We build the half that takes the booking. For the half that keeps the guest, these five questions are where I would start.
Common questions
Do I need SendSquared to use HomeRunner?
No. HomeRunner runs your direct booking website with or without a CRM behind it. The two work together through your PMS, and abandoned carts go from a HomeRunner site to SendSquared through the Conversion Kit add-on.
Which PMS works with both?
Guesty, Hostaway, Lodgify and Streamline are documented on both sides today. The compatibility table on our SendSquared page has the full list.
Can I run these checks on SendSquared itself?
Yes, and you should. Ask for a demo on your own data and run all five.