Windover’s Jess Cranney was one of the six fantastic awardees recognized at the North Shore Chamber’s annual Diamond Awards breakfast on August 21st. The Diamond Award honors outstanding women of influence and leadership in the region, and we are so proud that she was recognized for her commitment and passion for leading with purpose, empowering women, serving others, and making an impact.
Jess leads with intention, integrity, and an unwavering sense of purpose. As Project Manager of Field Support Team & Special Projects at Windover, Jess oversees a field services team of 25 carpenters and laborers. In an industry that is still predominantly male, Jess stands out not because she seeks the spotlight, but because she earns respect through hard work, humility, and her people-first mindset. She is a leader who rolls up her sleeves, listens deeply, and leads by example. Jess drives excellence while cultivating a team culture grounded in trust, support, and shared purpose.
In addition to her role at Windover, Jess also mentors students from Essex North Shore Agricultural & Technical School who are interested in careers in construction. She helps them build confidence, understand the realities of the industry, and envision a future for themselves. She embodies Windover’s mission and makes the construction industry more inclusive, compassionate, and forward-thinking in the process.
But Jess’s commitment to serving her community doesn’t stop there. Outside of work, Jess is a certified Search and Rescue K9 handler and volunteers her time selflessly, using her three black Labradors, Jackson, Bowyer, and Welles, to serve others in extraordinary ways. She participates in Search and Rescue missions, helping locate missing and deceased persons, offering critical support in moments of crisis. Additionally, she and her dogs visit local libraries to read with children, creating comforting, joyful experiences that foster literacy and emotional connection.
She is a licensed pilot and recently celebrated two years of active flight experience. Jess also held a 50-ton Master Captain’s License issued by the U.S. Coast Guard, reflecting her maritime leadership and operational expertise. In addition to her academic and technical credentials, Jess was recently elected Vice President of the Massachusetts Canine Response Team, a volunteer search and rescue organization she has proudly served for the past 10 years. Her diverse achievements highlight a rare blend of academic excellence, technical skill, and service-driven leadership.
Jess believes in lifting people up – especially young women in trades and construction. She serves not for recognition, but because she sees potential in others and wants to help them succeed. She empowers her team through active listening, clear communication, and support. She is a safe person to learn from, make mistakes around, and grow beside. By breaking stereotypes in the field and staying grounded in service, she quietly redefines what leadership can look like. Jess embodies Windover’s mission and makes the construction industry more inclusive, compassionate, and forward-thinking in the process.
Congratulations, Jess, on this amazing award and well-deserved recognition!
