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
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Chief of Staff at Wander for almost 5 years, leading cross-functional strategy and operational alignment.
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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.
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Works directly with executive leadership to execute company-wide priorities and long-term growth initiatives.
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Experienced in strategic planning, performance tracking, and organizational development.
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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
Matt says
“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.”
Staying at Wander Anchor Bay? We have the ultimate food guide with various cuisines to try during your stay.
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Jan 20, 2026Craving a great meal near Wander Bandon Beach? This read highlights local favorites for every mood, including fresh seafood shacks, oceanview dinners, relaxed coffee cafes, Italian inspired plates, and an easy grocery stop, helping you plan delicious days without overthinking where to go.
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Jan 26, 2026 Wondering where to get lunch or dinner near Wander Orford Cliffs? Look no further because we gathered the best eats in town just for you!
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Jan 20, 2026 At Wander, we understand that true luxury means inclusive travel experiences. To help you find the best destinations, we've analyzed America's top cities based on crucial accessibility factors like the number of wheelchair-accessible attractions, walkability, reliable public transport, and internet connectivity.
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Feb 18, 2026 Using data from Google, Tripadvisor, Instagram, and Numbeo, the team at Wander has ranked spots based on how often they're searched and posted about on Instagram. Destinations with lower search and social media engagement were considered more underrated. We then looked into how exciting their food and culture scenes are and how safe and clean they are. The result? A list of destinations that offer big adventures with fewer crowds.
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Jan 26, 2026 Explore the most exclusive US destinations with the Millionaire Vacation Index, ranking luxury hotspots by private air access, elite venues, and 5-star stays.
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Jan 30, 2026 The best time to visit California varies by season. Explore what spring, summer, fall, and winter offer to decide when is the best time to visit California.
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Feb 3, 2026 Discover the best time to visit San Diego with local tips on weather, crowds, events, and where to stay for a relaxed coastal escape.
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Jan 28, 2026 Discover the best places to stay in Santa Rosa, from vineyard escapes to scenic mountain retreats, with local tips on the right area for your trip.
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Jan 15, 2026 We analyzed data on trails, national parks, water sports, ski resorts, and camping sites to find the best state for an outdoor adventure in 2026!
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Jan 23, 2026 Why do vacation rentals disappoint? We surveyed US travelers to uncover the most common rental issues, how they affect trips, and what travelers expect next.
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Jan 28, 2026 Looking for the best vacation spots in Florida? Find sun-soaked beach towns, island hideaways, and luxury places to stay from Miami to the Keys.
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Feb 3, 2026 Find the best places to stay in Malibu, from Broad Beach to Point Dume, with this insider guide. Expect neighborhood insight and curated luxury vacation rentals by Wander.
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Feb 3, 2026 Find the best time to visit Palm Springs with our guide, covering seasonal weather insight, crowd notes, local tips, and luxury Wander stays for every desert season.
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Feb 4, 2026 Spring is one of the best times to experience Florida. From calm Gulf beaches to walkable coastal cities, these spring-ready destinations offer comfortable weather, lighter crowds, and outdoor experiences that shine between March and May.
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Feb 4, 2026 Discover the best time to visit Beverly Hills with local tips on weather, crowds, events, and where to stay for a stylish, stress-free trip.
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Feb 4, 2026 Explore the best luxury family vacation spots in Truckee, from walkable downtown stays to ski-side escapes and spacious mountain retreats. This guide highlights family-friendly neighborhoods and Wander homes designed for every season.
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Feb 12, 2026 Discover the best time to visit Pioneertown with seasonal weather insight, crowd patterns, and luxury desert stays near Palm Springs.
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Feb 5, 2026 April is one of Florida’s most rewarding months to travel. With warm water, clearer skies, and fewer crowds, these destinations offer relaxed beach days and outdoor experiences before summer heat arrives.
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Feb 5, 2026 West Hollywood offers many ways to experience LA, and where you stay shapes it all. This guide breaks down the best neighborhoods, highlighting walkable pockets, quieter streets, and refined Wander luxury rentals that make city living feel effortless.
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Feb 10, 2026 
