SendSquared
$2B+ Direct Revenue 15M+ Bookings 97% Retention

Direct Booking Growth for Property Managers |

Own Your Guest Journey. Drive Direct Revenue.

Turn guest data into direct bookings with the only AI-powered platform built for enterprise hospitality. Manage millions of guest relationships, automate personalized experiences, and watch your direct revenue soar... all from one unified platform.

ISO-Aligned Security
GDPR Compliant
99.99% Uptime SLA

0k+

Properties

0M

Guests

0%

Uptime SLA

0%

Direct Inc. YoY

Trusted by leading hospitality brands

SailRock
Royal Shell
Abode Luxury Rentals
Hodnett Cooper
The Cottages on the Keys
Get Away Vacations
Florida Vacation Homes
Five Star Properties

Platform

Everything You Need in One Platform

Purpose-built tools for hospitality teams to manage guest relationships, automate operations, and drive direct revenue.

Vacation Rental CRM

Purpose-built CRM for vacation rentals and resorts, connected directly to your PMS. Track guest preferences, owner relationships, and property performance with real-time synchronization.

PMS Connected Guest Profiles Owner Management

Unified Inbox

Complete conversation timeline across all channels in one view. Email, SMS, WhatsApp, and platform messages organized chronologically for seamless guest communication.

Conversation Timeline All Channels Unified View

Enterprise Voice System

In-house call center with soft clients, DND routing, and calls connected directly to PMS. Fully contextualized calls with guest history, call recording, and real-time analytics.

PMS Context Call Recording DND Routing

Voice AI Agents

AI-powered voice agents that handle calls naturally with full property context. 24/7 coverage with sub-second response times, natural conversation, and seamless warm transfer to human agents.

24/7 Coverage Natural Speech Warm Transfer

Lead Management

Most sophisticated lead management in hospitality. Lead categories, types, status tracking, and pipeline automation. Complete with notes, tags, assets, and custom fields.

Lead Pipeline Custom Fields Lead Automation

Task Automation

Link messages directly to tasks with monitoring and updates. Assign to specific agents or units, track completion, and automate follow-ups across your entire team.

Message Linking Agent Assignment Unit Tracking

Digital Guidebooks

Web-based guidebooks connected directly to PMS with all property photos. Add conditions for personalized content. Fully compliant with Airbnb off-platform policies.

PMS Photos Conditional Content Airbnb Compliant

Guest Verification

Complete guest verification with agent assignment. Guests upload IDs, remote service validates authenticity. Blue check verification displayed throughout system including calls.

ID Validation Blue Check Agent Assignable

Guest WiFi Management

Centralized WiFi management across all properties with custom splash pages, bandwidth control, and usage analytics.

Central Management Custom Branding Usage Analytics

Advanced Segmentation

Create dynamic guest segments based on behavior, preferences, and lifetime value. Power targeted campaigns across your entire portfolio.

Behavioral Segments LTV Analysis Predictive Modeling

AI Automations

Transactional messages for pre-stay and post-stay across all channels. Conditions on each node, time-based triggers, and full reservation context for intelligent automation.

Multi-Channel Conditional Logic Time Triggers

Website Chat Widget

Intelligent chat system with AI-powered responses, lead qualification, and seamless handoff to human agents when needed.

AI Chatbot Lead Qualification Live Agent Transfer

WhatsApp & Airbnb Integration

SendSquared is an official partner with WhatsApp and Airbnb. Accept reservations, message guests, and manage multiple accounts seamlessly. Track agent activity without sharing individual account access.

Official Partner Multi-Account Agent Tracking

LTV & Revenue Analytics

Lifetime value analytics connected directly to your PMS. Real-time revenue tracking, guest spending patterns, and predictive modeling for revenue optimization.

PMS Connected Real-time LTV Revenue Tracking

Email Marketing Platform

Marketing campaigns connected directly to PMS data. Automated segmentation, campaign performance tracking, and deliverability optimization for maximum engagement.

PMS Connected Auto Segmentation Performance Tracking

Postcard Marketing

Send physical postcards and letters to guests and owners directly from your CRM. Handwriting-style fonts, QR codes, UV coating, lifecycle tracking, and full campaign integration with email, SMS, and automations.

Direct Mail QR Codes Lifecycle Tracking

Reporting & Analytics

Executive summaries, agent productivity, lead compliance, call abandonment, survey scores, and email campaign revenue. Scheduled, exportable, and built for hospitality operators who need answers.

Executive Summary Agent Productivity Revenue Attribution

Owner Acquisition

Scout system to find every parcel in your market. Identify property owners with actual addresses and create custom proformas for targeted acquisition campaigns.

Market Scouting Owner Discovery Proforma Builder

Guest Surveys

Reservation-based surveys with NPS scoring, Z-score analysis, and multi-channel delivery. Agent notifications on low ratings enable real-time service recovery.

NPS Scoring Z-Score Analysis Agent Alerts

Salesrooms

Track owner interactions with your brand. Share proformas and property info via scannable postcards or email. Get critical information to owners instantly.

Owner Tracking QR Postcards Instant Sharing
Coming Soon

AI Agents

CRM agents that autonomously handle tasks, send emails, reorganize todos, build knowledge bases, and analyze sentiment scores for guests and owners.

Auto Workflows Sentiment Analysis Coming Soon

Testimonials

Trusted by Hospitality Leaders

“I can definitely attribute a good number of reservations to SendSquared. Between the easy follow-up communication within the system and the CRM pulling up information as a call comes in, our reservations team is being more intentional on their calls, resulting in better conversions.”

Brock Reich

Chief Operating Officer, Orlando Resorts Rental

“My experience with SendSquared has been eye opening. To be honest I didn't think something this good existed. Having all emails, texts, calls, web chat and marketing in one place has given my company and team a huge advantage. SendSquared has saved us both time and money which are very important factors to my small business of 50 luxury homes. The company is amazing to work with and extremely helpful whenever it was needed.”

Jessica Goree

Chief Operations Officer, Beach Reunion

“SendSquared is a game-changer for our resort operation. Its ability to integrate with our reservation software, providing real-time reservation information during phone calls, allows us the opportunity to build off of the rapport we've already created with our repeat guests. We're answering phone calls asking our guests how their kid's baseball season went, instead of asking for their names.”

Tim Oxborough

Reservation Manager, Sugar Lake Lodge

4.9/5

Average Rating

98%

Would Recommend

<90 days

Time to ROI

Ethos

A People-First Philosophy

At SendSquared, we believe the traditional boundaries between owners and guests are artificial. Owners are guests, and guests are owners. By breaking down these data silos, we unlock powerful insights into what truly defines both relationships. This unified perspective gives you the introspection needed to understand what makes an owner, and inversely, what makes a guest, creating exceptional experiences that transform both journeys.

LOYAL OWNER CURRENT OWNER FUTURE OWNER FUTURE GUEST CURRENT GUEST LOYAL GUEST 1 2 3 4 5 6 PEOPLE FOCUSED CUSTOMER JOURNEYS GUEST JOURNEY OWNER JOURNEY
1

Loyal Owner

Expanding your portfolio while maximizing value from existing properties

2

Current Owner

Building lasting relationships that drive retention and growth

3

Future Owner

Converting prospects with targeted communication that inspires ownership

4

Future Guest

Creating desire through personalized outreach that drives bookings

5

Current Guest

Delivering exceptional experiences that exceed expectations

6

Loyal Guest

Cultivating repeat business through recognition and exclusive benefits

Mobile App

Take SendSquared Anywhere

Manage your guests and reservations on the go with our powerful mobile app. Get instant notifications, respond to any message, and delegate or monitor your business from anywhere in the world.

  • Real-time guest messaging
  • Recorded phone calls on the go
  • CRM with PMS reservation data
  • Lead Management and Pipeline
Learn More About Our Mobile App
SendSquared Mobile Dashboard

Ready to Transform Your Operations?

Join industry leaders who trust SendSquared to manage millions of guest interactions and thousands of properties with unmatched efficiency.

Or call our enterprise team directly: 1-855-340-SEND

White-glove onboarding

Dedicated success manager

Custom integrations

24/7 enterprise support