Ashley Judge

Hi! Thank you for stopping by.

I’ve built and led companies at the intersection of storytelling, user experience, and revenue. My focus is on turning creative ideas into sustainable businesses that people care about. 

As Executive Director of Destination Salem, I oversee marketing for one of the most internationally recognized small cities in the U.S. My work focuses on modernizing a traditional industry—bringing digital transformation, data-driven strategy, and user experience thinking to destination marketing. Since joining in 2024, I’ve led the organization out of financial losses, strengthened operations, and built sustainable growth across advertising, retail, and digital channels.

Before that, I founded Always Fits, a bootstrapped e-commerce brand that grew to $10M in annual sales and earned national press for its humor, nostalgia, and loyal community. Running a small company from scratch taught me every side of business—creative, operational, and financial—and how to build something people genuinely care about.

I also serve as Vice Chair of The Salem Pantry, helping expand access to fresh food across the North Shore, and on the City’s Trust Fund Commission and Economic Coordination Task Force.