Dean D.Private profile: Upwork shows its earnings only to signed-in members, so we check it every few weeks, not daily. MRR here is a rough estimate (Upwork's six-month earnings ÷ months active). Last read Nov 5, 2026.

Hotel revenue management, email marketing and AI guest messaging expert who builds direct booking systems for independent and boutique hotels. I set up Klaviyo, configure your PMS data sync (Cloudbeds, Mews, Pricelabs, Pricepoint and others), integrate AI guest messaging through Akia and Whistle, build automated email flows, create guest segments, and train your team to run it. Your guest list is the most valuable asset your hotel owns. Every guest who checks out without entering your email system is a future booking you're handing to Expedia for a 15-20% commission. Most independent hotels have zero guest retention infrastructure. No post-stay follow-up. No seasonal re-engagement. No way to bring past guests back direct. That's the gap I fill. I'm not a consultant who theorizes — I own and operate a boutique riverfront hotel where I built this exact system from scratch. Every strategy I recommend is one I've deployed, tested, and refined with my own revenue on the line. Plus I have 10 years of email and SMS marketing experience. Any of these sound familiar? Paying 15-20% OTA commissions on guests who already know and love your property Guests check out and you never hear from them again No email capture on your website — visitors bounce and book through OTAs instead Your team sends occasional emails but there's no strategy or automation behind it You know email should work for your hotel but don't have the time or expertise to set it up properly Shoulder season and midweek rooms sit empty because you have no way to push targeted deals You're on Mailchimp or another basic tool that wasn't built for hospitality If this sounds familiar, you're not alone. Most independent hotels are leaving tens of thousands of dollars on the table every year in OTA commissions and lost repeat bookings. Here's what I build: Klaviyo setup and migration from Mailchimp or other platforms PMS data sync (Cloudbeds, Mews, and others) so every guest — OTA and direct — enters your marketing database AI guest messaging integration (Akia, Whistle) for automated upsells, review requests, and real-time guest communication Welcome flow for new email subscribers Pre-arrival sequence (timed drip based on check-in date) Post-stay flow (thank you, review request, direct rebooking offer) Win-back flow for lapsed guests (6-12 months inactive) Booking abandonment flow for website visitors who don't complete a reservation VIP and repeat guest flows with exclusive offers Audience segmentation — OTA vs. direct guests, first-time vs. repeat, by season, by value Website email capture popups with lead magnets 12-month campaign calendar mapped to your property's seasonality Team and VA training so your people can operate the system independently This is not an agency retainer. I build the system, train your team, and hand it off. You own it. Your team runs it. I'm there for strategic guidance as long as you need me. Tools I work with: Klaviyo · Cloudbeds · Mews · Akia · Whistle · Duda · Zapier/Make · Google Business Profile Message me and let's talk about your property.