After months of building, testing, and refining AI workflows, we finally developed a model that promises to work! We launched three agents, each focused on its own aspect of STR management, and a team member who loves musicals called them Tom, Dick, and Harry (lol).

In a nutshell:

Tom — Guest Communications & CRM.

Tom operates a dedicated guest‑communication line; his job is to automatically send welcome messages immediately after booking, payment reminders, check‑in instructions, mid‑stay follow‑ups, and checkout guidance. Tom also handles inbound guest messages. If he knows the answer, he responds instantly. If not, he escalates to a human. He is particularly useful in registering and prioritizing maintenance requests and complaints.

Dick — Back‑Office Operations & Analytics.

He is essentially Copilot (comes with the MS Office suite) with a set of unique structured prompts. He scans Outlook, extracting what's important from a sea of spam. Integrated with Excel, Dick tracks financials, generates performance reports, and runs revenue and expense analysis. He also supports creative tasks like social posts, image generation, and website updates.

Harry — Calendar Coordination & Dynamic Pricing

Harry manages calendars, availability, and dynamic pricing. Over time, our goal is to train Harry to orchestrate Tom and Dick — to create a fully automated STR management ecosystem.

As of now, we are excited about watching these guys start working. I'd love to hear from other STR operators who are embracing AI — what models or workflows have proven effective for you?