
✦ Open to Work
Property Manager | STR Deal Finder | Sand Stays | 10+ yrs | 100+ Properties Managed
Portland, Maine · 10 yrs in STR · Remote
Hi, I’m Derek! I’ve spent over 10 years managing short-term rentals and motels, helping property owners simplify their operations and improve their results. As the CEO of Sand Stays LLC, I work with owners to tackle the challenges of managing properties, from handling guest communication to boosting bookings and streamlining day-to-day operations. I’m all about creating systems that make life easier for property owners—whether it’s setting up self-check-in, improving online presence, or taking over the tasks they don’t enjoy. My goal is always to maximize income and provide great guest experiences, without adding stress to the owner’s plate. Here are a few highlights of my experience: -Managed over 200 short-term rentals, gaining hands-on expertise across diverse properties. -My team and I have hosted over 25,000 reservations and helped owners obtain more than 10,000 5-star reviews, with those numbers continuing to grow. -Operated and improved the performance of 5+ motels. -Used creative financing strategies—like owner financing, lease purchases, and lease options—to put deals together and unlock opportunities. -Worked with 50+ software tools and services specific to short-term rentals, giving me deep insight into selecting the right tech for any business. I also run STR Deal Finder, where we help investors source and structure short-term rental opportunities without needing to purchase property upfront. I enjoy working with property owners who are ready to grow or just want to take a step back from the hands-on work. Outside of work, you’ll often find me brainstorming new ideas, supporting my team, or helping my daughter with her homework.
CEO
Sand Stays LLC
2016-10 – Present
PMS
Channel Manager
Revenue
Accounting
Guest Comms
Maintenance
Housekeeping
CRM
Operations
Other