Step 1 · Email
Re: Birthday dinner for 24 — Sofia
Step 2 · Email
Menu options + deposit details
Automation sequences
Follow up until it's booked.
Winston runs the message chains you never have time for — inquiry replies, deposit nudges, review asks — by email, and stops the moment a guest answers.
You choose the mode per sequence: draft-for-approval or fully automatic. Winston never double-sends.
This is a sequence. Steps, waits, and exit rules — built once, run on every inquiry.
Follow-ups that run themselves. Winston keeps every conversation moving while your team runs the room.
Starts from real signals.
New inquiry, unpaid deposit, finished visit, three days of silence — pick the trigger and Winston enrolls the guest automatically.
One playbook, your own inbox.
Every step sends from your connected Gmail or Outlook mailbox — so replies land in the inbox your team already works.
Runs on schedule, stops on reply.
Waits are business-day aware. The moment a guest writes back, the sequence exits and Winston hands you the thread.
Marta Vidal
Enrolled 3 days ago
Email nudge in 2 days
Jordi Puig
Enrolled 2 days ago
Email in 3 days
Anaïs Laurent
Enrolled yesterday
Review ask in 1 day
Marta Vidal
Enrolled 3 days ago
Email nudge in 2 days
Jordi Puig
Enrolled 2 days ago
Email in 3 days
Anaïs Laurent
Enrolled yesterday
Review ask in 1 day
Marta Vidal
Enrolled 3 days ago
Email nudge in 2 days
Jordi Puig
Enrolled 2 days ago
Email in 3 days
Anaïs Laurent
Enrolled yesterday
Review ask in 1 day
Marta Vidal
Enrolled 3 days ago
Email nudge in 2 days
Jordi Puig
Enrolled 2 days ago
Email in 3 days
Anaïs Laurent
Enrolled yesterday
Review ask in 1 day
Tomás Ferreira
Enrolled 6 hours ago
Pre-arrival note in 2 days
Mia Torres
Enrolled 1 hour ago
Deposit reminder in 2 days
Tomás Ferreira
Enrolled 6 hours ago
Pre-arrival note in 2 days
Mia Torres
Enrolled 1 hour ago
Deposit reminder in 2 days
Tomás Ferreira
Enrolled 6 hours ago
Pre-arrival note in 2 days
Mia Torres
Enrolled 1 hour ago
Deposit reminder in 2 days
Tomás Ferreira
Enrolled 6 hours ago
Pre-arrival note in 2 days
Mia Torres
Enrolled 1 hour ago
Deposit reminder in 2 days
“Deposits used to take four calls. Now they're paid before I've thought about them.”
Núria Serra
Events Manager · Fieldstone & Co, Barcelona
Personal at any volume. Every message reads like you wrote it — because Winston wrote it about them.
Every step, on the record. Enrollment, replies, bookings, and exits — visible per guest, per sequence.
[ 01 ]
Watch the journey.
See exactly which step each guest is on, and why.
[ 02 ]
Measure what lands.
Replies, bookings, and drop-off per step — in one view. Roll results up in Reporting
[ 03 ]
One-click control.
Pause, skip, or pull a guest out of a sequence instantly.
[ 04 ]
Send at the right moment.
Business-day waits and quiet-hours rules, tuned for hospitality.
Sequences plug into everything Winston knows. Signals in, follow-ups out — one front office.
Start your 14-day free trial.
- Connect your inbox — Winston starts drafting follow-ups the same day.
- Install a template: deposit chasing, review requests, win-back. Marketplace templates
- Approve every send until you trust it on autopilot.
Read-only inbox access until you flip a sequence on. Simple pricing — see plans