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Home / About / Directors
Home / About / Directors


Leslie Goldsmith, Program Director

My first sailing season with OWSA was in 2014 and I have loved the experience of sailing on the Columbia on Wednesday Night Sails, meeting new people and gaining more confidence in my sailing skills. I grew up sailing in Buzzard's Bay, near Cape Cod, in small boats and overnight cruising on my dad's sloop. I am a recently retired preschool teacher. My husband Reed and I moved to Portland in 2011 to be near our children and grandchildren. I am excited to join OWSA's Board as Program Director.


Jen Wiseman, Education Director

Jen is relatively new to sailing. After becoming an OWSA member in 2017, she quickly caught the bug, found some openings and started to volunteer. She is thankful to OWSA for the personal thresholds she has overcome in such a short period of time and is always ready to pay it forward. She has learned to sail small boats through the BOAST Program and is excited to share the knowledge she has learned with you.


Katie Drew, Social Director

Katherine started sailing when she was 24 years old and got her first sailboat; a 18' Hunter. She completed her first sailing class at Willamette Sailing Club. Katherine joined OWSA in 2012.

She participates regularly in the Wednesday Night Sails. Katherine recently completed the First Mate Program. She enjoys crewing on different boats at Portland Yacht Club, Set Sail for a Cause, Mauna Elliott & SYSCO races. She just started volunteering with the SYSCO race events.


Kathleen Winterling, Fundraising/Swing Director

Kathleen moved with her family to the Pacific Northwest from South Carolina in 2000 and reclaimed her dream of sailing. She joined OWSA in 2016 and immediately jumped in taking all the courses OWSA offered. To deepen her understanding of sailing, she was part of the OWSA BOAST program, sharing ownership of a Cal 29 with 5 fellow sailing sisters. There she learned skills about boat maintenance where she was often seen tinkering with the Ferryman diesel engine, polishing fuel and changing filters. Kathleen became active in racing on Team Wildheart as a Headsail Trimmer and recently is getting experience on the bow learning Spinnaker. What Kathleen enjoys most is the combination of artistry and science sailing requires.

When she is not on the water you'll find her on the golf course, volunteering, or on a committee boat doing photography. She serves as a Director for OWSA focusing on Fundraising.


Melissa Cearlock, Operations Director, Webmaster

Melissa is native to the Vancouver/Portland area, sailing since the age of 6. Traveling offshore, exploring the Puget Sound, and many other places even taught kids to sail at West Moorland Pond while standing in water up to her waist, and in the tropics while stationed in Guam during her time in the Navy. Melissa got her first boat in 2007, a 26ft Paceship and spent many weekends on the Chesapeake Bay, MD. Returning to the Pacific NW without her boat in late 2013 Melissa discovered OWSA at the Portland Boat Show in Jan of 2014 and joined that Feb. She has taken classes, volunteered at OWSA events and is looking forward to many more.

Melissa served as our 2015-2017 Treasurer, Email Coordinator and Webmaster.

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