**The problem it solves** Vacation rental management companies relying on basic PMS messaging and disconnected email marketing tools cannot effectively build guest relationships, run targeted direct booking campaigns, or manage high volumes of inbound calls without adding staff. **What SendSquared does** SendSquared is a CRM, marketing automation, and guest communication platform founded in 2018 and based in St. Paul, Minnesota. Built for vacation rental management companies and resort operators, it integrates with major PMS systems to unify guest profiles, automate the full booking lifecycle, and support direct booking growth through owned communication channels. **How it works** Bidirectional PMS integrations sync reservation data, guest profiles, and messages in real time with Guesty, Hostaway, Streamline, Barefoot, Escapia, Cloudbeds, and others. A unified inbox threads email, SMS, WhatsApp, Airbnb, VRBO, Booking.com, and phone calls into a single per-guest conversation view. Guest profiles include custom fields, tags, lifetime value tracking, deduplication, and full activity timelines. Marketing automation covers PMS-segmented email with Smart Send AI timing, SMS and postcard marketing, Wi-Fi capture, and more than 20 automation trigger types across pre-arrival, mid-stay, and post-stay workflows. An AI voice agent answers inbound calls with sub-one-second response, resolving 65 to 75 percent without human intervention. **Who it's for** Property management companies and resort operators managing large guest databases who need segmentation-driven marketing alongside day-to-day operational communication, focused on growing direct booking revenue through owned channels.
Listed on STR Market Map, the short-term-rental software marketplace.