Who’s behind Pretty Picky?

The Pretty Picky Team – Scott, Karen, Jim, Blake & Kris

Jim and Karen Decker
Jim and Karen started Pretty Picky Properties as a result of meeting a need they had themselves.  After deciding to rent their prized cottage in Brewster, they became frustrated with the lackluster marketing and absence of on-site attention their property received from their conventional rental broker.  So they did it themselves. They tapped Jim’s 35+ years of marketing and advertising experience and applied Karen’s personal relationship management skills, honed in 30+ years as an educator. They began greeting arriving guests in person at their cottage. As good as their cleaning service was, they developed their own, separate check list of safety, presentation and detailing steps and diligently executed them every rental turnover day to thoroughly prepare the property for arriving guests.  To this day, in-person on-site guest greeting and the Pretty Picky Property Prep Punch List remain key added values in the company’s service mission.

Along the way, Karen and Jim also discovered how good it feels to personally welcome families to their long anticipated summer vacation. That good vibe motivated them to become licensed agents, then brokers, so they could create a new kind of rentals management company.  In 2003, Pretty Picky Properties was founded, representing only select properties and serving owners and guests at a level unavailable before on the Cape.

Today, Jim manages most of Pretty Picky’s marketing activities, while Karen is the Chief Financial Officer and remains very active in guest and owner relationship management.

Jim is also a nearly 20-year volunteer for the Brewster Whitecaps of the Cape Cod Baseball League.  He is the club’s communications director and often throws batting practice. Karen allows him to do this.

Besides their Brewster cottage, Karen and Jim have a home on Long Pond in Harwich.

Blake Decker
With 13 years of sales and marketing experience Karen and Jim’s son, Blake, was an obvious choice to help manage and grow Pretty Picky.  Blake started full time with Pretty Picky in 2009. He has been licensed since 2006. He is now the company’s CEO and often consults with rental guests exploring ownership, especially from an investment perspective.

Before joining the family business, Blake was the original “sales guy” for Cape Cod Beer.  This experience helped him develop an intimate knowledge of the local Cape economy and geography.  Blake owns a home in Brewster, where he lives with his wife, Jessie, and their two young sons.

Scott Cheyne (say it “Chain”)
Scott is a long time Decker family friend who was recruited to join the “PPP” team.  Scott has owned and operated a successful marketing research company for many years.  His experience with ethnographic and qualitative analysis lends itself to perfecting Pretty Picky’s guest service and management operations.  He is Pretty Picky’s Chief Operating Officer and takes the lead on most systems and technology issues.

Scott, his wife Patricia and Marley (four legs) split their time between the Cape and St Petersburg, Florida.

Kris Ramsay
Kris joined Pretty Picky in 2015 as its full-time General Manager. He is a licensed real estate agent and is involved in all aspects of the company’s management activities, such as rental guest and owner service, new business development  and property management.

Before Pretty Picky, Kris was the Director of the Orleans Conservation Trust, where his responsibilities included land acquisitions, land management, stewardship, education, and outreach. He currently sits on the board of Friends of Pleasant Bay. He lives in Brewster with his wife, Anna, and their daughter.