Success story
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HostWell is a San Francisco-based vacation rental management company founded by Keith Freedman, delivering full-service management with a strong focus on guest experience and owner protection.
Location: San Francisco, US
Number of listings: 47
Using Hostfully since: 2019
Favorite features: Automated messaging with triggers, Custom fields, Unified inbox, and digital guidebooks
Hostfully lets us deliver personalized guest communication at scale without the manual work,” said Keith Freedman. “It saves us time, reduces stress, and actually improves the guest experience at the same time.
HostWell built its reputation by obsessing over details. Based in San Francisco, the vacation rental management company focuses on delivering stress-free revenue for property owners while preserving a strong human touch for guests. Even as the portfolio grew, founder Keith Freedman believed personalized communication mattered. “When we include the owner’s name in messages instead of our company name, guests treat the property with more respect,” said Keith. “It’s a simple way to protect our clients’ assets.”
To preserve that level of personalization, HostWell sent check-in instructions manually. Every message was customized with the guest’s name, the owner’s name, reservation details, and property-specific information. While the approach worked, it came at a cost. Each message required careful copy-pasting, editing, and double-checking. Errors were always a risk, and last-minute bookings frequently interrupted staff workflows.
“We were doing everything right for the guest,” said Keith, “but the process behind the scenes was not scalable.”
As HostWell continued to grow, it became clear that manual messaging, even with templates, would eventually slow the business down.
Hostfully’s unified inbox, automated triggers, and custom fields transformed how HostWell handled guest communication. Once properties were imported into Hostfully, Keith started by creating a digital guidebook for each listing. These guidebooks centralized check-in instructions, house rules, local recommendations, and check-out details, all accessible through a unique URL.
“The guidebook became the anchor for everything,” said Keith. “Once we had that, automation finally made sense.”
Using Hostfully’s automated messaging triggers, HostWell set check-in messages to send three days before arrival. Guest names, host names, reservation dates, access details, and the guidebook link were dynamically inserted using custom fields. The timing proved critical. “If you send instructions too early, guests lose them,” Keith explained. “Three days out hits the sweet spot.”
Automation also solved the stress of last-minute bookings. If a guest booked within the three-day window, Hostfully automatically sent the check-in information immediately. “Guests think someone is sitting behind the screen responding instantly,” said Keith. “In reality, it’s Hostfully doing the work for us.”
By eliminating repetitive manual tasks, HostWell freed up significant staff time while delivering consistent, polished communication across its entire portfolio.
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What started as a time-saving initiative led to unexpected gains. With personalized, well-timed messages and professional digital guidebooks, guests felt supported throughout their stay. HostWell added an automated message one day before check-out with property-specific instructions, further reinforcing the sense of attentiveness.
“The surprise was the reviews,” said Keith. “Guests started mentioning how communicative and attentive the host was, and when we checked, no one on our team had actually spoken to them.”
As five-star reviews increased, HostWell gained pricing power. Without upgrading furnishings or adding amenities, the company was able to raise average daily rates on select properties. Automation not only reduced stress and workload, it directly improved revenue and guest perception.