Matt Kowalewski
Chief of Staff
Matt Kowalewski is the Chief of Staff at Wander, where he works closely with executive leadership to guide company strategy and ensure disciplined execution across teams.
Since joining in June 2021, he has played a central role in aligning operations, growth initiatives, and long-term planning as Wander continues to expand its footprint in luxury vacation rentals across the United States, Canada, Colombia, and more.
At Wander, his focus is clarity and accountability. He translates ambitious goals into structured roadmaps, supports cross-functional collaboration, and ensures that internal systems evolve alongside the company’s rapid growth. His work behind the scenes helps maintain the high standards guests associate with every Wander home.
Career highlights
Chief of Staff at Wander for almost 5 years, leading cross-functional strategy and operational alignment.
Founder of Exotic Auto Sales, building and scaling the company from inception for over half a decade. His work in this space resulted in millions of dollars of sales.
Works directly with executive leadership to execute company-wide priorities and long-term growth initiatives.
Experienced in strategic planning, performance tracking, and organizational development.
Known for bringing structure, accountability, and measurable outcomes to high-growth environments.
Expertise
- Operational strategy
- Executive partnership
- Cross-functional leadership
- Organizational planning
- Business performance analysis
- Process optimization
- Growth execution
Education
Iona University – Bachelor of Business Administration in Business, Management, Marketing, and Related Support Services
“Growth is exciting, but without clarity it becomes noise. My role is to create structure around ambition, so teams know what matters most and how their work connects to the bigger picture. When priorities are clear, and accountability is shared, execution accelerates, and the results become sustainable.”
— Matt says
