Automation Engine
Automations
On trigger, if this, then that, across every channel your guests use. 20+ trigger types fire from reservations, leads, surveys, WiFi logins, guidebook views, gap nights, and more. Conditional branching with 12 operators and dozens of condition types ensures the right message reaches the right guest at the right time.
Reservation Triggers
The guest journey drives your automations. Trigger workflows on reservation created, modified, cancelled, status change, and type change. Time-based reservation triggers fire relative to arrival, departure, or contract date. Send a pre-arrival message 3 days before check-in, a mid-stay check-in on day 2, and a review request 1 day after checkout. All powered by live PMS data.
- Reservation created, modified, cancelled, status, and type triggers
- Time-relative triggers based on arrival, departure, and contract date
- Pre-arrival, during-stay, and post-departure automations
- Real-time PMS data ensures accurate trigger evaluation
Lead & Sales Triggers
Every lead lifecycle event fires a trigger. New lead, updated, closed, won, lost, reopened, assigned, and follow-up due date. Combine lead triggers with conditions on lead status, type, source, estimated value, and category to build targeted sales automations. When a lead is won, auto-send a booking confirmation. When a lead goes cold, fire a drip sequence.
- Lead new, updated, closed, won, lost, reopened, and assigned triggers
- Follow-up due date triggers for time-sensitive lead nurturing
- Conditions on lead status, source, category, and estimated value
- Direct integration with lead pipeline and disposition workflows
Survey & NPS Triggers
React to guest feedback in real time. Survey triggers fire on sent, started, completed, and individual question answered. Rating triggers fire on low scores (1-3) and high scores (8-10). NPS triggers fire separately for promoters (9-10), passives (7-8), and detractors (0-6), letting you route each segment into the right follow-up workflow.
- Survey sent, started, completed, and question-answered triggers
- Low and high rating triggers for immediate service recovery or upsell
- NPS promoter, passive, and detractor triggers for segmented follow-up
- Combine with agent notification actions for real-time escalation
Channel & Engagement Triggers
SMS opt-in, opt-out, and inbound message triggers. WhatsApp and Airbnb inbound message triggers with new-thread detection for Airbnb. Email verification events. WiFi login triggers when a guest connects at your property. Guidebook triggers when a guest views their guidebook or accepts legal terms. Gap night triggers fire on vacancy windows for occupancy marketing.
- SMS inbound, opt-in, opt-out, and chat inbound triggers
- WhatsApp inbound and Airbnb inbound with new-thread detection
- WiFi login triggers for property-level guest capture
- Guidebook loaded and legal terms accepted triggers
Group, Tag & Property Triggers
Group join and leave triggers fire when contacts enter or exit segments, powering automations based on dynamic audience membership. Tag join and leave triggers fire when labels are applied or removed during calls, inbox interactions, or batch operations. Contact property change triggers fire when specific fields update, such as first name, last name, or last email open date.
- Group join and leave triggers for segment-based automations
- Tag join and leave triggers for label-based workflow routing
- Contact property change triggers on field updates
- Cart abandonment triggers for e-commerce recovery flows
Conditional Branching
Not every guest should get the same message. Conditions evaluate contact properties, reservation data, lead status, campaign engagement, SMS opt-in status, tag membership, segment membership, survey responses, Airbnb thread data, and custom fields, with 12 operators including equals, contains, greater than, is null, and in-list. Block-based logic groups conditions with AND within blocks and OR between blocks.
- 12 condition types spanning contacts, reservations, leads, and campaigns
- 12 operators including equals, contains, greater/less, is null, and in-list
- AND logic within condition blocks, OR logic between blocks
- Segment membership conditions for nested audience targeting
Multi-Channel Actions
Send email, SMS, WhatsApp, Airbnb messages, postcards, and surveys as workflow actions. Create tasks, add or remove tags, and fire outbound webhooks for third-party integration. Each action supports template selection, merge field personalization, from-address configuration, and smart send optimization. Target the contact, the reservation's travel agent, or the assigned agent.
- Email, SMS, WhatsApp, Airbnb, postcard, and survey send actions
- Task creation and tag add/remove as workflow steps
- Outbound webhook actions for third-party integrations
- Send-to targeting: contact, travel agent, or assigned agent
Time Delays & Scheduling
Arrange precise timing within your workflow tree. Relative delays wait a configurable number of seconds, minutes, hours, or days. Absolute delays wait until a specific time of day. Intelligent time-aware delivery prevents messages from going out in the middle of the night. Nest delays within conditional branches for sophisticated timing logic.
- Relative delays in seconds, minutes, hours, or days
- Absolute delays that wait until a specific time of day
- Time-aware delivery prevents off-hours message sending
- Nestable delays within conditional branch paths
Visual Flow Builder
Build automations visually with a flow chart editor. Each workflow stores its visual layout alongside the execution logic; what you see is what runs. Parent-child action trees create branching paths. Duplicate entire workflows with one click to iterate on proven flows. Organize workflows into folders for team management.
- Visual flow chart editor with drag-and-drop action placement
- Branching paths with parent-child action trees
- One-click workflow duplication for rapid iteration
- Folder organization for managing large automation libraries
Process Future & Backfill
New automations don't have to start from zero. The process-future feature queues existing entities (future reservations, tagged contacts, or group members) through a new workflow. Backfill a welcome sequence for all upcoming reservations, or run a re-engagement flow against an existing segment, without waiting for new triggers to fire.
- Backfill future reservations through new workflows
- Process existing tagged contacts through new tag-based flows
- Queue current group members through new segment-based automations
- Selective backfill doesn't duplicate for already-processed contacts
Gap Night Automations
Fill vacant nights between reservations automatically. Gap night triggers fire based on arrival and departure windows around vacancies. Configure minimum gap size, minimum reservation nights, specific reservation types, and target units. When a gap opens in your calendar, marketing messages fire to past guests who fit the stay window, driving occupancy without manual effort.
- Gap night arrival and departure triggers for vacancy marketing
- Configurable minimum gap size and minimum stay requirements
- Filter by reservation type and specific unit IDs
- Automated outreach to past guests who fit the vacancy window
Workflow Gallery & Templates
Don't start from scratch. The workflow gallery provides pre-built automation templates for common hospitality scenarios: post-stay review requests, pre-arrival check-in sequences, owner reporting cadences, and lead follow-up drips. Browse by category, preview the flow, and import directly into your account. Customize triggers, conditions, and actions to match your operations.
- Pre-built workflow templates for common hospitality automations
- Browse by category with thumbnails and descriptions
- One-click import into your account with full customization
- Active and inactive template management for seasonal workflows
Testimonials
What Our Clients Say
“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
“We manage over 300 properties and SendSquared has been instrumental in streamlining operations. Consolidating all communications into one platform while maintaining personalized guest experiences has been transformative for our team.”
Shawn Montgomery
Director of IT, Collins Vacation Rentals
“SendSquared is an indispensable tool for us! One of their significant standout attributes is its ability to centralize communication channels, offering a one-stop solution for managing various modes of interaction. This consolidation streamlines our workflows, enhancing our efficiency and productivity. What's better is their customer support elevates the user experience. Their responsive team is always ready to assist, going above and beyond to ensure seamless integration and utilization.”
Fred Cercena
CEO & Founder, GetAway Vacations
Ready to Get Started?
See how SendSquared can transform your hospitality operations.
Schedule a Demo