In this edition of The Insider, we were joined by Arthur Colker (@StayFi_Arthur), founder and CEO of StayFi, to talk all things guest marketing, email automation, and putting your data to work.

If you’ve been collecting guest emails but haven’t done much with them, or you’re unsure how to set up campaigns that drive repeat direct bookings, this recap is packed with practical insights. Arthur answered questions from Hospitable hosts covering automation logic, campaign best practices, segmentation, and more.

Here’s the recap. ​ 

Q: Can I use StayFi to send emails, not just collect them?

A (Arthur): Yes. After signing up through StayFi's Hospitable partner link, you can use our built-in email marketing tool. It’s free for up to 200 subscribers and pulls in your guest data from Hospitable.

You can also collect additional data using our Pre-Arrival forms, even if you’re not using our WiFi hardware.

[Automation Logic & Guest Timing]

Q: Guests aren’t opting into my Pre-Arrival link. How can I increase submissions?

A (Arthur): You're doing the right thing by sending the link multiple times. To improve opt-ins, focus on what the guest gets after completing the form: early check-in, house manual, local recommendations. Be specific and make it worth their time.

Q: What’s the best way to trigger welcome emails when Airbnb emails arrive late?

A (Arthur): Use a delay-based trigger: send the welcome email 1 day after booking, which gives time for Airbnb guest emails to sync. This method works for both Airbnb and Vrbo guests, so you don’t need separate automations.

Q: Can StayFi trigger an email when a guest leaves a 5-star review in Hospitable?

A (Arthur): Not yet; Hospitable’s 5-star review data isn’t passed into StayFi. You could use a workaround like Zapier or manual tagging to trigger a thank-you email encouraging social engagement.

[Campaign Strategy & Re-engagement]

Q: I’ve collected 1,000+ guest emails but haven’t used them. How should I start?

A (Arthur): Start with three automations:

• WiFi Welcome
• Post-Departure
• Stay Anniversary

Then use the Upcoming Availability feature to market:

• Last-minute weekend deals (great for drive-to markets)
• High-demand dates (e.g. New Year's, Spring Break)

For re-engaging older contacts, begin with a plain-text, first-person email introducing yourself and inviting them to book direct for the best rate. It doesn’t need to be polished—authentic is better.

Tip: Plain-text emails are more likely to land in a guest’s primary inbox and are more effective for engagement than image-heavy designs.

Q: How often should I send newsletters or promotions?

A (Arthur):

• Newsletters: Start with once a month.
• Promotions/availability updates: Send them when there’s a business reason; like cancellations or dates you want to fill.

Q: Should I segment my list, or send to everyone?

A (Arthur): With 1,000 contacts, segmentation likely isn’t worth the effort. Use dynamic tags (like the Property Name they stayed at) to personalize emails without creating multiple segments.

Q: What’s a good campaign cadence?

A (Arthur): Minimum one campaign per month, to stay top of mind. Increase frequency when there's urgency or availability to fill. The most successful users aren’t afraid to reach out when there's a reason.

Q: I manage multiple properties: should I use separate lists?

A (Arthur): No need unless you operate in vastly different markets. One list is sufficient. Use personalization to refer to the specific property each guest stayed at.

Q: We’re seeing strong delivery and open rates, but no click-throughs. What should we do?

A (Arthur): A few things to consider:

• Apple Email Privacy skews open/click stats, so treat them as directional only
• 40% open rate and 2–5% click-through rate (CTR) is typical
• Try a plain-text version of your email
• Link your logo to your website
• Test campaigns that offer time-sensitive discounts

Arthur’s take: The real goal is visibility. Most guests won’t book immediately, but you want them to remember you when they do.

[What Top Hosts Do Differently]

Q: How are the top 1% of StayFi users different?

A (Arthur): They:

• Create property-specific splash pages and HomePages that promote upsells (like early check-in or real estate services)
• Send Pre-Arrival links via Hospitable messaging and SMS
• Combine email + SMS marketing to promote last-minute deals and high-demand dates
• Use promo codes to track repeat direct bookings
• Send campaigns consistently—not just during high season

Common Mistakes:

• Not using the data once it’s collected: engagement drops the longer you wait
• Over-polishing emails: authenticity often outperforms design, especially for hosts

--

Thank you ​@StayFi_Arthur for sharing strategic insights on converting guest data into bookings. Hosts: whether you’re just getting started or ready to scale your direct channel, StayFi's tools give you the building blocks to market like a pro.

Good to know:

• Save on StayFi: Hospitable hosts that integrate their account with StayFi get access to StayFi’s email marketing tool free for the first 200 contacts, plus savings on higher tiers (more).

• Build a Direct Booking Vacation Rental Brand with StayFi: watch our Hospitable Masterclass with Arthur for tips on creating a brand, driving repeat bookings, and boosting your direct booking profits.

You can find the whole Insider conversation here:

Want to see someone featured in a future Insider? Let us know.