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Bob Miller

Executive Director

Bob Miller, the Executive Director of Lakeside Assisted Living at Mallard Landing, is an Eastern Shore native. He is committed to the quality of life offered on the Shore and has spent his career working primarily with seniors and healthcare. Strategically he focuses on building teams with passion and commitment to the Discovery Senior Living Pillars of Excellence, including teamwork, integrity, performance, accountability, compassion, hard work, and creativity. Bob received his undergraduate at Lee University, Cleveland, Tennessee, and his Masters’ degree at Eastern University, St. Davids, Pennsylvania. In his spare time, Bob likes to spend time with his family and play piano semi-professionally in local restaurants.

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Ashley Haldeman

Senior Lifestyle Coordinator

Ashley Haldeman is the Senior Lifestyle Counselor at Lakeside at Mallard Landing Senior Living Community. Ashley began her career in senior living 6 years ago as a Business Office Manager then moved to Director of Sales and Marketing. Most recently she worked as a liaison for hospice. She has a passion for senior care and is dedicated to being a knowledgeable resource for the community. When Ashley is not working you can find her chasing her 2 children around or crafting.


Leah Walker

Senior Lifestyle Counselor

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Chasity Wright

Director of Celebrations

Chasity has worked in the human services field for almost ten years, with a passion and experience working with the aging population. Chasity is a native of Atlanta, GA, and holds a Bachelor of Arts in Sociology and a Bachelor of Arts in Social Work. She brings a warm and charismatic presence when engaging and fellowshipping with residents. Chasity enjoys traveling internationally and exploring and trying new restaurants.

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Diana Oakley

Director of Health and Wellness

Diana Oakley is the Director of Health and Wellness at Lakeside at Mallard Landing. Diana has 26 years of nursing experience. Her background includes bedside hospice and oncology. Diana is a Colorado native but has lived all over the country. She has three grown children and spends her free time sharing her love of fitness with others through teaching classes at the local YMCA.

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Jason Pilchard

Director of Facilities

Jason Pilchard has lived on the Eastern Shore for over 51 years. Jason has worked in the senior care industry for over seven years. He has worked in the Maintenance and Construction fields for over 20 years and in the I.T. industry for ten years. Jason enjoys spending time with his three children, pursuing outdoor recreation, and camping outside of work.

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Cherilynn Parks

SHINE® Memory Care Director

Cherilynn was born and raised on Long Island, NY calling the Eastern Shore home since 2019. She has worked 17 years in the senior living industry, starting as an activities aide, becoming an assistant activities director, and then activities director in skilled nursing facilities since 2017. Cherilynn obtained her Bachelor’s Degree in Therapeutic Recreation with a concentration in Gerontology. She enjoys spending time with her husband and nine-month-old son. Cherilynn loves riding her horses and looking after her dogs, goats, and chickens on her small farm.

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Sade Bacon

Business Office Manager

Sade has ten years of experience in the senior care industry, beginning with volunteering in her senior year of high school. She is an Eastern Shore native with an Associate of Arts and Science degree in Accounting, Finance, and Business Management. Outside work, Sade loves traveling and spending time with her family.