Direct Booking Growth with AI Voice |
SendSquared. Own Your Guest Journey. Drive Direct Revenue.
SendSquared turns guest data into direct bookings — 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.
0k+
Properties
0M
Guests
0%
Uptime SLA
0%
Direct Inc. YoY
Everything you need in one platform.
Disconnected tools and data slow you down. SendSquared connects every guest touchpoint — phone, SMS, email, AI receptionist, CRM, and PMS — in one place, so hospitality teams can drive direct revenue, automate operations, and deliver better guest experiences.
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.
Unified Inbox
Complete conversation timeline across all channels in one view. Email, SMS, WhatsApp, and platform messages organized chronologically for seamless guest communication.
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.
AI Voice Agents
Recover $165K+ annually from missed calls with AI voice agents that resolve 65-75% of inquiries autonomously. Sub-second response times with full PMS context, dedicated Sales and Support modes, and seamless warm transfer when human touch is needed.
Lead Management
Most sophisticated lead management in hospitality. Lead categories, types, status tracking, and pipeline automation. Complete with notes, tags, assets, and custom fields.
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.
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.
Guest Verification
Complete guest verification with agent assignment. Guests upload IDs, remote service validates authenticity. Blue check verification displayed throughout system including calls.
Guest WiFi Management
Centralized WiFi management across all properties with custom splash pages, bandwidth control, and usage analytics.
Advanced Segmentation
Create dynamic guest segments based on behavior, preferences, and lifetime value. Power targeted campaigns across your entire portfolio.
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.
Website Chat Widget
Intelligent chat system with AI-powered responses, lead qualification, and seamless handoff to human agents when needed.
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.
LTV & Revenue Analytics
Lifetime value analytics connected directly to your PMS. Real-time revenue tracking, guest spending patterns, and predictive modeling for revenue optimization.
Email Marketing Platform
Marketing campaigns connected directly to PMS data. Automated segmentation, campaign performance tracking, and deliverability optimization for maximum engagement.
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.
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.
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.
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.
Salesrooms
Track owner interactions with your brand. Share proformas and property info via scannable postcards or email. Get critical information to owners instantly.
AI Agents
CRM agents that autonomously handle tasks, send emails, reorganize todos, build knowledge bases, and analyze sentiment scores for guests and owners.
Model Context Protocol
Every LLM, Squared by SendSquared
SendSquared runs a Model Context Protocol server so any LLM — Claude, ChatGPT, Grok, Gemini, and more — can query your CRM and trigger workflows. Ask questions in plain language, surface insights, and act on guest data from the AI client of your choice.
Claude Anthropic via MCP 
ChatGPT OpenAI via MCP 
Grok xAI via MCP 
Gemini Google via MCP 
Llama Meta via MCP 
Mistral Mistral AI via MCP 
Perplexity Perplexity via MCP 
DeepSeek DeepSeek via MCP Ask in Plain Language
Query reservations, lifetime value, campaign performance, and call analytics from any MCP-compatible client.
Trigger Workflows
Send messages, create leads, update guest records, and fire automations from a conversation.
Tenant-Scoped Tokens
Granular permissions match your ACL controls. Revoke or rotate tokens instantly.
Full Audit Trail
Every read and write logged with the model, agent, and timestamp for compliance.
Ethos
A People-First Philosophy
At SendSquared, we believe the boundaries between property owners and guests are artificial. Owners are guests, and guests are future owners. By breaking down these data silos, we unlock the insights that turn one-time bookings into long-term partnerships and lifelong direct guests. For hotels and resorts, your B2B relationships — corporate accounts, group organizers, travel advisors, wedding planners — drive recurring revenue alongside your individual guests. By breaking down silos between sales, front desk, marketing, and the PMS, we unlock the insights that turn one-time bookings into long-term partnerships and lifelong direct guests.
Top right on the wheel
Loyal Owner
Long-tenured property owners become your highest-margin partners — they refer, retain, and reinvest. Treat them like the asset they are with white-glove communication and shared performance dashboards.
Right on the wheel
Current Owner
Communicate proactively about bookings, revenue, and property performance. Owners who feel informed renew — owners who feel ignored shop their portfolio.
Bottom right on the wheel
Future Owner
Every guest is a potential owner. Segment by stay frequency, spend, and engagement to identify the right ones, then nurture them with portfolio insight and ownership economics.
Bottom left on the wheel
Future Guest
Win-back campaigns, abandoned-booking follow-ups, and lookalike audiences all start with unified guest data. Personalize outreach by destination, season, and past behavior.
Left on the wheel
Current Guest
Real-time messaging, AI-assisted answers, and contextual upsells turn a one-time stay into a story worth telling. Be available, useful, and silent in equal measure.
Top left on the wheel
Loyal Guest
Returning guests cost a fraction to retain — and they spend more per stay. Loyalty workflows, exclusive offers, and early booking windows do the compounding.
Top right on the wheel
Loyal Corporate Account
Recurring annual corporate contracts, brand-direct accounts, and travel-advisor partners. They book year after year and bring high-margin volume — treat them like the strategic accounts they are with dedicated reps and quarterly business reviews.
Right on the wheel
Active Group / Event
Weddings, conferences, sports teams, corporate retreats. Multi-room bookings with a dedicated planner. Real-time messaging with the organizer keeps room blocks tight and ancillary revenue (F&B, AV, transport) compounding.
Bottom right on the wheel
Future Account
RFPs, prospective corporate accounts, and group leads in your sales pipeline. Segment by company size, segment, geography, and decision-maker engagement so your sales team focuses on the highest-fit opportunities.
Bottom left on the wheel
Future Guest
Booked but not yet arrived. Pre-arrival messaging, room-ready confirmations, and digital guidebooks set the tone before the guest walks through the door.
Left on the wheel
Active Guest
Currently on property. Real-time messaging, AI-assisted answers for amenity and policy questions, and well-timed contextual offers (spa, dining, late check-out) turn a stay into a story worth telling.
Top left on the wheel
Loyal Guest
Top-tier returning guests with multiple stays and high lifetime value. They get the suite upgrade, the early check-in, and the personal welcome from the GM. Loyalty workflows make these moments automatic, not accidental.
Hover any number on the wheel to expand that stage.
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
Industry Advocacy & Events
Powering The Voices Of Our Industry
Every advocacy group and event we sponsor receives a complimentary SendSquared subscription to power their member outreach and event marketing — the same platform our hospitality customers use, gifted to the organizations that move the industry forward.
Running an industry event or advocacy group? We support qualified events and organizations that help the hospitality industry grow — regional VRMAs, summits, conferences, podcasts. Qualified groups receive a subscription to power their awareness campaigns. Learn more →
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
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
SendSquared is the vacation rental CRM and hotel CRM built for property managers, hotels, and resort operators. Email, SMS, WhatsApp, Airbnb, web chat, and voice all land in a single unified inbox, threaded by guest with full PMS context — so your team responds from one screen instead of switching between five tools. Outbound campaigns run from the same workspace through PMS-segmented hotel email marketing with Smart Send AI timing. Inbound calls are answered around the clock by a hospitality-trained AI voice agent with live PMS lookups and warm escalation to your team, while branded digital guidebooks deliver check-in details and property info before guests arrive and on-property guest wifi sign-in captures verified contact data tied to every reservation. Every interaction feeds guest loyalty workflows and lifetime value tracking that turn first-time stays into repeat direct bookings.
The unified inbox is one piece of SendSquared's hotel messaging stack — every channel (SMS, WhatsApp, Airbnb, email, voice) threaded against one PMS-linked guest profile.