Portrait by ChiChi Ubiña

YWCA Greenwich will be holding its 8th Annual Women Who Inspire Awards to recognize exceptional women in our community. YWCA Greenwich’s Women Who Inspire Awards was established to recognize and celebrate outstanding women who have excelled in philanthropic, professional, and volunteer pursuits. Importantly, these honorees have enriched the lives of many in our community. This event acknowledges the changes in society that have led to the fluidity of work/life pursuits for women of today.

For more information and to purchase tickets, click here.

Alyssa Gillego, MD is a breast surgical oncologist at Greenwich Hospital and an assistant professor of surgery at Yale School of Medicine. She is deeply dedicated to the comprehensive care of patients diagnosed with breast cancer, guiding them from diagnosis through treatment and recovery with both clinical expertise and compassion. Dr. Gillego performs complex procedures including lumpectomies, mastectomies, and axillary lymph node surgeries, and is known for her patient-centered approach and collaborative style of care.

In addition to her clinical practice, Dr. Gillego has contributed to the advancement of her field through scholarship and leadership. She has authored several peer-reviewed journal articles and two book chapters, and she is the recipient of both a Physician Recognition Award at Greenwich Hospital and the 2024 Norman Roth Leadership Award. She serves as Team Leader of the Breast Cancer Program at Greenwich Hospital and is a member of the medical advisory board of Breast Cancer Alliance, where she helps guide community education and support initiatives.

Dr. Gillego received her undergraduate degree from New York University, where she completed her premedical

studies while also pursuing art history and competing on the women’s varsity tennis team. She earned her medical degree from Far Eastern University in the Philippines, then completed her general surgery residency at Maimonides Medical Center and a breast surgical fellowship at St. Luke’s–Roosevelt Hospital Center. She joined Greenwich Hospital in 2017 and is honored to work alongside colleague, Dr. Barbara A. Ward.

Dr. Gillego’s path to medicine began early, shaped by a family deeply rooted in healthcare. Both of her parents were physicians whose dedication to their patients profoundly influenced her. Her mother, Dr. Azucena Gillego, was a respected primary care physician in private practice, and her father, Dr. Virgilio Gillego, served as a radiologist at Coney Island Hospital. Surrounded by relatives in medicine, she grew up immersed in examples of commitment, integrity, and compassionate patient care.

YWCA Greenwich holds special meaning for Dr. Gillego and her family. A proud mother of a YWCA alumna, she has watched her 11-year-old daughter, Luna Winterhoff, grow through experiences at YWCA Greenwich—from preschool and summer camp to her very first ballet class—strengthening the family’s connection to this vibrant community resource.