Jennifer Ingraffea is a seasoned executive leader with over 25 years of experience in the retail, apparel, product merchandising, and management sectors. In July 2025, Jennifer became the CEO of Pendleton Woolen Mills; a family-owned business since its founding in the 1860s. Before joining Pendleton, she served as Chief Product & Merchandising Officer at The North Face, prior to which, she worked at Nike in a number of high-level executive leadership roles. Jennifer and Roy discuss her new role and dig into essential leadership skills like curiosity, stewardship, and much more.

Highlights from our conversation include:

Core beliefs, values, and principles in Jenn’s leadership playbook (2:53)
Leading through cycles of massive consumer and retail evolution (5:39)
Identifying areas of a business that are in need of clarification and simplification (7:36)
Aligning a team towards a long term vision (11:01)
Lessons learned around hiring and team building at major brands (14:58)
How Jenn developed her hiring process and philosophy (17:07)
What a great leader looks like to Jenn (18:36)
Valuable traits that Jenn identifies when hiring direct reports (22:58)

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