What do fine arts, Saks Fifth Avenue, Tesla, and global disaster relief have in common? Lyndsay Skeegan's career.Lyndsay is the Chief Operating Officer of ShelterBox USA, a global humanitarian organization that provides emergency shelter to families who have lost their homes to disasters and conflict. ShelterBox has supported over 3 million people across 25 years of operations — and Lyndsay oversees everything from finance and HR to data and analytics and sales operations. Before getting there, she built one of the most unconventional planning careers you'll ever hear about.She started in a contemporary art gallery in New York City. Then, determined to break into fashion, she did something most people wouldn't: she took a night and weekend job at Banana Republic to earn her shot at a buyer position, went back to the recruiter who'd turned her down, and got hired. From there she climbed through Saks Fifth Avenue, MoMA, Coach, and a series of luxury retail startups — mastering merchandise planning by borrowing textbooks, cold-asking colleagues for their favorite Excel formulas, and learning everything on the job.Then came Tesla. Lyndsay joined as part of the team building the direct-to-consumer planning and allocation function from the ground up. She describes that era the way a lot of Tesla alumni do: forged in fire, urgency as a daily operating mode, and a bond with teammates that has outlasted the company itself. After Tesla, she helped spin up a logistics and warehouse program at an EV startup, then took a deliberate sabbatical to pursue passion projects — launching a free financial education program for women and marginalized communities, developing a horse-based experiential leadership program, and running her jewelry company with 100% of proceeds going to charity.Now at ShelterBox, she's applying every tool in that toolkit — strategic planning processes, KPI infrastructure, AI experimentation, living SOPs — in service of the mission: no one without shelter.This conversation is a masterclass in what it looks like to be biased toward action, comfortable with chaos, and deeply committed to turning both into process.Topics Covered:- How Lyndsay broke into merchandise planning with zero retail experience- The career path from fine arts → Saks → MoMA → Coach → Tesla → nonprofit COO- What Tesla taught her about grit, urgency, and building teams under resource constraints- How she thinks about SOPs as living documents — not locked-in rules- ShelterBox USA's mission and how it responds to global disasters and conflict- Balancing urgency with a healthy, sustainable team culture- How the nonprofit sector is approaching AI adoption (and where it lags behind)- The mock disaster deployment she participated in just weeks into her role- Her horse-based leadership development program and why horses make great coaches