Former Director, Sales Enablement & Talent Development
Square
Stephanie Cwynar is a seasoned revenue enablement and learning leader with 15+ years of experience driving go-to-market success, scalable learning strategies, and cross-functional initiatives that deliver measurable impact. She specializes in global enablement, product education, and L&D, having supported 1,500+ product launches and led programs that elevate sales performance and customer support.
At Square, she developed a global sales enablement strategy, optimizing onboarding, leadership development, and product training across remote and on-site teams. Previously, at Meta, she built and led the customer service enablement team, scaling programs across 23 call centers worldwide. Earlier, at LāOrĆ©al, she played a key role in launching the ombrĆ© hair color trend and was a Beauty Shakers Award Finalist for innovative go-to-market strategies.
Stephanie holds a Masterās in Education from Rutgers and certifications in Instructional Design, Product Marketing, and Women in Leadership. Currently pursuing a culinary certificate at Cook Street, she enjoys hiking in Colorado, experimenting in the kitchen, and creating pottery.