Executive Interview Series: Matthew Kraus on Long-Term Craftsmanship in a High-Speed World

Today we’re interviewing Matt Kraus, CEO of Skyline Windows, a fourth-generation
company known for custom windows and façade systems across New York City’s most
iconic buildings.

Though Skyline operates in manufacturing and WIN Brands Group in e-commerce, Matt
and WIN’s CEO Kyle Widrick share a common challenge: how to scale without
compromising quality, identity, or purpose. This interview looks at how a legacy business like Skyline evolves with modern tools and principles—while staying true to what made it enduring in the first place.

Q: Matt, WIN Brands Group is all about acquiring great brands and helping them
scale. How does that mindset resonate with how you’ve grown Skyline?
A: While acquisitions aren’t our focus, we do take a long-term approach to scaling
deliberately. For us, that means expanding into new markets like Boston, Philadelphia, and D.C. - but only once the systems, training, and team infrastructure are in place to uphold our quality at scale. Like WIN, we’re constantly refining operations without losing sight of what makes our brand trusted. Our product is physical, permanent, and highly visible. If we scale carelessly, the flaws show up in the skyline itself.

Q: WIN emphasizes shared operational systems and centralized expertise.
How does Skyline maintain consistency across projects?
A: Standardization has been critical to our growth. From estimating and engineering to
manufacturing and installation, we’ve invested heavily in systems that ensure every project meets the same standards. What Kyle and WIN are doing digitally on the consumer side, we’re doing physically in construction: building scalable infrastructure that preserves quality and protects the brand.

Q: Kyle Widrick talks about the value of founder insight and grit. You’re a
fourth-generation leader—how do you balance legacy with reinvention?
A: I respect the legacy, but I don’t romanticize it. My great-grandfather was a tinsmith.
Today, we’re running factories with robotic equipment, advanced machinery, and AI-powered cutters and glass handlers. Legacy gives us credibility and culture, but
reinvention is what keeps us relevant. I think that’s similar to what WIN looks for when
evaluating brands—a strong identity, but also a willingness to evolve.

Q: WIN is focused on customer-first thinking. What does that mean in a
business like Skyline?
A: For us, the “customer” isn’t just the developer or architect—it’s also the building owner 10, 20, even 30 years from now. Windows are a decades-long investment. Customer-first means asking: Will this perform in extreme weather? Will it meet acoustic and thermal standards in 2040? Our timescale is different from DTC, but the principle is the same: delivering long-term value people can rely on, even if they don’t see it immediately.

Q: Both Skyline and WIN operate across channels: physical, digital, B2B, and
more. How do you see omnichannel dynamics influencing building and
construction?
A: In construction, the equivalent of “omnichannel” is integration. Architects, engineers,
manufacturers, and installers all need to be aligned. Increasingly, that collaboration is
digital—3D modeling, cloud-based design reviews, automated production—and it’s
pushing coordination earlier in the process. Like WIN, we believe better alignment drives better outcomes.

Q: What advice would you offer entrepreneurs or executives scaling something
with staying power?
A: Know who you are, then build systems that protect that identity as you grow. Never
scale at the expense of trust. Skyline has endured for over a century because we’ve
remained consistent in our quality, even as tools and technology have evolved. WIN’s
model shows you can scale quickly—but only if you have the right framework to sustain it.

Closing Thought:
From precision-engineered facades to best-in-class e-commerce brands, Skyline Windows and WIN Brands Group demonstrate how companies can scale with intention, balance legacy with reinvention, and stay relentlessly focused on customer value—whether in the digital cart or on a city skyline.