Frequently Asked Questions

SendSquared is an all-in-one CRM and marketing platform built for enterprise hospitality. It integrates directly with your property management system to unify every guest, owner, vendor, and lead into a single platform. From there, your team can communicate across email, SMS, voice, WhatsApp, Airbnb, and web chat — all from one place. It covers the entire guest lifecycle: lead capture, reservation sales, pre-arrival communication, in-stay engagement, post-stay surveys, review management, remarketing, and owner retention.

SendSquared is designed for property management companies, vacation rental operators, hotels, and resorts. Our clients typically manage anywhere from 50 to 5,000+ units and need a unified platform to handle guest communication, marketing, lead management, and owner relations at scale.

SendSquared offers two pricing plans: SendSquared Enterprise for vacation rentals and hotels focused on reservation sales, and SendSquared Owner Enterprise for owner development and acquisition. Pricing is based on your company's scale — units for rentals, keys for hotels. Contact us directly for a customized quote.

We do not currently offer a free trial, but you can book a demo to see SendSquared in action and get a personalized walkthrough of the platform tailored to your business.

SendSquared Enterprise typically takes six to eight weeks for full implementation, while SendSquared Owner Enterprise takes up to six weeks. This includes PMS integration, number porting, call menu configuration, automation setup, and team training. Your dedicated implementation manager handles the process end to end.

Contact our support team at support@sendsquared.com or call/text +1 855-340-7363. Every support request is handled by our internal engineering team — not offshore contractors. You can also reach us through the contact forms on our website or through the in-app chat.

SendSquared integrates directly with your PMS through a real-time API connection. Guest profiles, reservation data, revenue, unit information, and owner records sync automatically. Every contact carries their full reservation history, unit preferences, revenue totals, and stay dates. We integrate with Barefoot, Escapia, Streamline, Guesty, Hostaway, Cloudbeds, RDP, RoomKeyPMS, StayNTouch, Versa, Visual One, and more.

Yes. Each contact supports multiple email addresses with primary designation, SMTP verification, and error tracking. Mobile and home phone numbers are stored separately. WhatsApp IDs and Airbnb IDs link to their respective messaging channels, giving you every way to reach a guest in one profile.

SendSquared automatically detects duplicate contacts based on email, phone number, and name matching. You can merge contacts manually or let the system suggest merges. When contacts are merged, all communication history, reservations, tags, and activity timelines are combined into a single unified profile.

Yes. Property owners live in the same CRM as guests. You can track owner relationships, manage owner communications, send owner-specific marketing campaigns, and use our Owner Enterprise plan for owner acquisition with trackable postcards, interactive proformas, and tax data integration.

SendSquared supports SMS, email, voice calls, WhatsApp, Airbnb messaging, web chat, and web forms — all in a single unified inbox. Every conversation is threaded by contact so your team sees the full communication history regardless of which channel the guest used.

Every message across every channel appears in one workspace. Conversations are threaded by contact with agent assignment and routing. Your team can respond to SMS, email, WhatsApp, and Airbnb messages from the same screen. Real-time push notifications ensure nothing gets missed, and canned responses speed up replies for common questions.

Yes. SendSquared includes a full enterprise voice system with call queues, IVR menus, call plans with time-based routing, barge/whisper/silent monitor, call recording and transcription, dispositions, smart routing, DID management, voicemail, hold music, agent status, directories, and mobile soft clients. Every inbound call shows the guest's PMS data on screen before the agent picks up.

Voice AI provides AI-powered phone agents that handle calls naturally with full property context. In Sales Mode, the AI agent qualifies inquiries, answers availability questions, and warm-transfers qualified leads to your team. In Support Mode, it answers guest questions using your knowledge base. Voice AI uses tool calling for real-time data access, supports warm escalation to human agents, and provides full session transcripts and analytics.

Yes. SendSquared supports Airbnb message sync with multi-account and non-PMS unit support. Airbnb messages appear in your Unified Inbox alongside SMS, email, and other channels. You can also build automations triggered by Airbnb reservations, and our Digital Guidebooks are fully compliant with Airbnb's Off-Platform Activity policy.

Our website chat converts web visitors into persistent SMS conversations. When a guest chats on your website, they provide their real phone number. The conversation transitions to SMS so you maintain the connection after they leave your site. It includes AI-powered automated responses, live agent handoff, drip messaging sequences, and direct CRM lead integration.

SendSquared provides a full email marketing suite with three editor types: a drag-and-drop editor for building responsive emails from content blocks, a rich text editor for quick campaigns, and raw HTML support for custom designs. You get PMS-powered segmentation with 50+ reservation operands, AI-trained Smart Send timing that delivers at each contact's optimal time, multi-brand management, agency draft mode, resend-to-unopens, and revenue attribution that connects every campaign to bookings.

Smart Send is our AI-trained delivery optimization. Instead of blasting your entire list at once, Smart Send analyzes each contact's engagement history and delivers their email at the time they're most likely to open it. This dramatically improves open rates and reduces the chance of landing in spam.

Yes. Our Postcard Marketing feature lets you send physical postcards and letters directly from your CRM. Choose from five template sizes, handwriting-style addressing, QR code placement, UV coating, and livestamping. Every postcard is individually trackable with full lifecycle tracking from print to delivery. It integrates with your campaigns and automations just like email and SMS.

SendSquared links email campaigns to PMS reservations through soft association. The campaign revenue report shows which reservations were influenced by which campaigns, including arrival and departure dates, open and click rates, and attributed revenue. You can group performance by month, week, or day of week to see which campaigns actually drive bookings.

Yes. If you manage multiple brands or properties under one company, SendSquared provides full data isolation between brands. Templates, senders, campaigns, unsubscribes, and segments all scope to brand. Agency draft mode lets marketing partners build campaigns that require client approval before sending.

Nearly everything. The visual flow builder supports 20+ trigger types including reservation events, lead status changes, survey responses, campaign engagement, WiFi logins, and tag/group changes. Actions include sending email, SMS, WhatsApp, Airbnb messages, postcards, creating tasks, adding tags, updating fields, and firing webhooks. Conditional branching lets you build different paths based on reservation data, contact properties, or engagement history.

Yes. Most of our clients automate the full pre-arrival to post-stay sequence: booking confirmation, pre-arrival check-in instructions, digital guidebook delivery, mid-stay check-in, post-stay survey, review request routing (low scores to your team, high scores to review sites), and remarketing campaigns. All triggered automatically by PMS reservation data.

SendSquared automatically identifies gaps in your reservation calendar and matches them against past guests who fit the stay window. Multi-channel gap offers go out via email, SMS, or postcard with personalized pricing. Stay extension and early arrival offers target existing reservations that could be extended to fill adjacent gaps.

Yes. The full lead management suite includes pipeline kanban boards, custom categories and statuses, agent assignment, automated follow-up sequences and drip campaigns, lead source attribution, lost reason tracking, task pairing, Chrome Extension capture, and mobile lead management. Leads are fully integrated with the CRM so all communication history stays attached.

SendSquared includes native call tracking with Phone Flip Scripts that route callers through tracked numbers. Every call is logged with dispositions, and lead source attribution tracks the entire path from initial contact through to booked revenue. You can see exactly which marketing channels are driving calls and which calls are converting to bookings.

Yes. Our Owner Enterprise plan includes individually trackable postcards with QR codes, an interactive proforma tool (Salesroom) that generates dynamic financial projections for prospective owners, and integration with tax and property data to identify acquisition targets in your market.

SendSquared sends reservation-based surveys automatically after checkout. Surveys include NPS scoring with Z-score trend analysis to identify properties or teams trending up or down over time. Multi-channel delivery supports email, SMS, and interactive web surveys. Low NPS scores trigger agent alerts for immediate follow-up, while high scores route guests to public review sites.

Digital Guidebooks are browser-based property guides that pull PMS data automatically. They support nine content block types including check-in instructions, house rules, area guides, maps and photos, WiFi credentials, and gap night upsells. Conditional visibility rules show different content based on reservation dates, unit type, or guest attributes. Guidebooks also handle ID verification, legal term acceptance, and are fully Airbnb Off-Platform compliant.

Guests upload identification documents through their digital guidebook before arrival. Your team reviews submissions through a secure admin interface with access logging. Email validation and legal term acceptance are also built in. Verified guests receive a blue check badge on their contact profile for quick visual confirmation.

SendSquared turns your property WiFi into a guest data capture tool. When guests connect to your WiFi, they authenticate through a branded captive portal that captures their contact information. This data links to their PMS reservation automatically, building a complete guest profile that includes both booking data and on-property behavior. WiFi logins can trigger automations, and the guest topology data feeds into lifetime value calculations.

Segments are dynamic groups powered by live PMS data. You can build segments using 12 condition types and 12 operators — targeting by reservation dates, revenue, unit type, booking channel, contact properties, lead status, campaign engagement, survey responses, SMS opt-in status, tags, groups, and custom fields. Segments update automatically and show pre-send counts of reachable, verified, and opted-in contacts.

The reporting suite includes executive summaries, agent productivity dashboards, lead compliance reports, call volume and abandonment analytics, agent booked revenue, lead source and revenue attribution, SMS and email response duration, email campaign revenue, survey score reports, automation and IVR analytics, daily snapshots, owner reservation pacing, and cart abandonment recovery tracking. Reports can be scheduled for automatic delivery and exported.

Yes. Our iOS and Android apps give your team full access to contacts, the unified inbox, tasks, lead management, and professional calling on the go. Agents receive real-time push notifications for new messages and can respond across SMS, email, and other channels directly from the app.

SendSquared integrates with Barefoot, Escapia, Streamline, Guesty, Hostaway, Cloudbeds, RDP, RoomKeyPMS, StayNTouch, Versa, Visual One, Airbnb, and Google Travel. Each integration provides real-time bi-directional data sync for reservations, guest profiles, unit information, and revenue data.

Yes. The Airbnb integration supports unified messaging, multi-account management, non-PMS unit support, automations triggered by Airbnb reservations, and Off-Platform compliant digital guidebooks. The Google Travel integration enables free booking links with PMS-powered availability sync, connecting search traffic to your direct booking pipeline.

Yes. Beyond PMS integrations, SendSquared supports webhooks for connecting to external systems, a Chrome Extension for lead capture from any website, and web form integration for capturing leads from your own site. The automation engine can fire webhook actions to push data to any third-party system that accepts HTTP requests.