SendSquared

What SendSquared is

SendSquared is a CRM and marketing platform for vacation rental managers, hotels and resorts, and its email marketing sends campaigns and automated pre-stay and post-stay messages built on live reservation data from the operator's property management system (PMS). The homepage describes "Hospitality CRM, AI Voice, unified inbox, and marketing automation for vacation rental, hotel, and resort operators," and says it is "the only AI-powered platform built for enterprise hospitality." The company behind it is AdBase, Inc., doing business as SendSquared.

The site puts its scale as "$2B+ Direct Revenue • 15M+ Bookings • 97% Retention". Email is one channel in a larger system that also covers SMS, WhatsApp, Airbnb messaging, web chat, phone and AI voice, direct mail and guest WiFi, all tied to one guest record.

What a sender gets

Email marketing on PMS data

The email product is described as "Marketing campaigns connected directly to PMS data. Automated segmentation, campaign performance tracking, and deliverability optimization for maximum engagement." The company's comparison page adds the detail a marketer needs: SendSquared "includes a drag-and-drop email editor, pre-built hospitality templates, dynamic content blocks, and deliverability monitoring," and every email can personalize with reservation dates, property names and guest history. Outbound campaigns, the homepage says, run "through PMS-segmented hotel email marketing with Smart Send AI timing"; the menu lists this send-time feature as Guest Time AI, "AI-powered send-time optimization to reduce fatigue and lift response."

Segments that follow reservations

Segmentation is where SendSquared puts its weight. It says it segments "by check-in date, property type, booking source, stay history, lifetime value, and 40+ PMS-powered conditions," and that every segment "rebuilds itself as reservations change." The examples on the page are concrete: guests who have a future reservation and check in within 7 days, for pre-arrival messages; high-value guests whose last stay was over 18 months ago, who have nothing booked and whose lifetime value is above $5,000, for win-back; repeat guests with at least 2 stays at oceanfront properties and 3 or more nights per stay, for premium upsells; and guests whose last NPS score was below 8 but who are coming back, for personal outreach before arrival. The homepage adds behavioral segments, lifetime value analysis and predictive modeling.

Automation

Automations are multi-channel workflows with "Conditions on each node, time-based triggers, and full reservation context," covering transactional messages before and after a stay across all channels. SendSquared lists the triggers it fires from: booking confirmed, check-in tomorrow, checkout complete, anniversary approaching and gap night detected. Solution pages built on these include OTA-to-direct conversion, cart abandonment recovery by SMS and follow-up, guest loyalty and repeat booking, gap night fill for empty nights and shoulder seasons, and a pre-arrival to post-stay journey.

Other channels

The unified inbox brings "Email, SMS, WhatsApp, and platform messages" into one conversation timeline per guest. SendSquared says it is "an official partner with WhatsApp and Airbnb", and its digital guidebooks are "Fully compliant with Airbnb off-platform policies." Voice runs through an in-house call center system with call recording and DND routing, plus AI voice agents that the company says "resolve 65-75% of inquiries autonomously" and can "Recover $165K+ annually from missed calls". An AI website chat qualifies leads and hands off to staff.

Postcard marketing sends "physical postcards and letters to guests and owners directly from your CRM," with handwriting-style fonts, QR codes, UV coating and lifecycle tracking, integrated with email, SMS and automations. Guest surveys are reservation-based with "NPS scoring, Z-score analysis, and multi-channel delivery," and alert agents on low ratings.

Growing the list

A WiFi captive portal gives centralized WiFi management "with custom splash pages, bandwidth control, and usage analytics," and a WiFi email capture solution collects email from every occupant who signs in. Website form integrations and call tracking feed leads into a lead pipeline with categories, statuses, custom fields and automation.

Reporting

Reporting covers "Executive summaries, agent productivity, lead compliance, call abandonment, survey scores, and email campaign revenue," and reports can be scheduled and exported.

Owner marketing

For vacation rental managers, SendSquared also markets to property owners. A Scout system finds parcels and owners in a market and builds proformas for acquisition campaigns, Salesrooms share proformas and property details "via scannable postcards or email", and owner performance reporting keeps homeowners informed.

Integrations and AI

The site names its PMS integrations: Barefoot, Escapia, Guesty, Hostaway, Lodgify and Streamline for vacation rentals, and Cloudbeds, Fullsteam, Maestro, Oracle OPERA, RDP, RoomKeyPMS, StayNTouch, Versa and Visual One for hotels and resorts. Channel integrations include Google Travel and HomeRunner, plus phone call tracking and website forms.

SendSquared runs a Model Context Protocol server "so any LLM (Claude, ChatGPT, Grok, Gemini, and more) can query your CRM and trigger workflows," with tenant-scoped tokens and a full audit trail of every read and write. There is also a SendSquared CLI. Built-in AI agents "autonomously handle tasks, send emails, reorganize todos, build knowledge bases, and analyze sentiment scores".

Pricing, security and support

The site sells through demos, and its enterprise demo form asks for property count in bands from 30-100 properties up to 5,001+; it publishes no prices and offers an ROI calculator instead. It says the platform includes everything "in one platform at one price."

The homepage shows "ISO-Aligned Security", "GDPR Compliant" and a "99.99% Uptime SLA", and the footer reads "ISO-Aligned · GDPR Compliant · FCC Registered". A status page is linked.

Enterprise customers are promised "White-glove onboarding", a "Dedicated success manager", "Custom integrations" and "24/7 enterprise support", and the site runs a Help Center, FAQ and phone line for its enterprise team. For switching, "Our onboarding team migrates your contact lists, email templates, automation workflows, and sending domains," and the company says most hotels are fully operational "within two weeks with zero downtime." iOS and Android apps cover messaging, recorded calls, the CRM and the lead pipeline. Industry advocacy groups and events the company sponsors receive a complimentary subscription.

Customer quotes include FieldTrip, which says consolidating WiFi, smart locks, verification, guidebooks and communications "has cut our vendor costs by 60%", and Host and Home, which says it is adding "on average 10 doors a month".

Who SendSquared suits

SendSquared suits a vacation rental manager, hotel group or resort operator running one of its supported PMS systems that wants guest email, SMS, WhatsApp, calls and direct mail driven from live reservation data, with owner acquisition as a bonus for rental managers. Its demo form starts at 30 properties, and its support promises are written for enterprise teams.

It is not built for anyone outside hospitality, and a single small property without a supported PMS would be buying a CRM, call center and WiFi system to get an email tool.