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logo design

Wingman Solutions

THE BRIEF

Wingman Solutions is an Ontario-based MSP (Managed Service Provider). They’d hired Araia Marketing to develop a marketing strategy that would secure more interest, more trust, and more business. The first priority of this marketing strategy? To elevate the brand identity to better position this IT company as a leader in the market. In partnership with Araia Marketing, I was brought in to lead the visual rebrand.

SCOPE OF WORK

Brand Identity Design

social media designs

THE CHALLENGE

Lacking Visual Distinctiveness

From the audience’s perspective, choosing an MSP can feel daunting and unclear. As they evaluate providers, they’re searching for signals of trust before deciding who to engage. The Wingman Solutions brand lacked the visual distinction needed to stand out and position itself as a compelling, credible choice.

"But Don't Change the Logo"

The Wingman brand already had a strong logomark. Designed by one of the business’s founders, they didn’t want to lose the iconic mark they’d had since day one. The goal of this rebrand was to reimagine the brand experience but take the logomark with it.

apparel-brand-design-for-IT-company.jpg

THE STRATEGY

Call it Modernization or Call it a Designer’s Eye

Beyond the logo, the original brand identity—experienced primarily through the website—felt basic and purely functional. It did little to spark curiosity or engage the senses. This is a common challenge among startups that have approached branding on their own. Our goal in the rebrand was to modernize the brand’s image through intentional design decisions, creating a cohesive system that could support long-term growth.

social post design for IT company
embossed business card design for IT company

STRATEGY

Technology—but Make it Human

The biggest opportunity that existed in the IT space was to make the brand more personable. This meant moving away from technical jargon and generic tech visuals, and instead highlighting the people behind—and using—the technology. By creating a sense of familiarity, the brand builds connection. And when people feel seen, they’re far more likely to engage.

website design IT business
custom icon design for services

DESIGN

Tidying Up the Negative Space

There were very deliberate choices made when it came to the brand typography. I wanted the logo to feel sweet and gentle, while remaining professional and polished. This was achieved with a serif typeface that had soft corners and curves to present a compassionate brand. An elegant but very legible script typeface was used in secondary logo designs that made the brand feel personal and feminine. These typefaces were chosen for how they move, breathe, and hold space.

original logo design

rebranded logo design

DESIGN

Here’s Our Angle: We Customize to Unify

The previous logo typography was ultra-fine and felt disconnected from its bold monogram counterpart, which also affected legibility at smaller sizes. To address this, I selected a bold, geometric sans serif that shares similar visual characteristics, bringing cohesion to the combination mark. To further unify the system, select letterforms were customized to echo the strong angles of the logomark, reinforcing a consistent and intentional visual language.

branding for IT company

DESIGN

Designing for Versatility

The brand was limited with just one logo design, which could only perform well in horizontal spaces. This rebrand involved expanding the logo suite. By providing a range of logo design orientations, the brand’s logo could adapt to any space regardless of size or shape.

brand identity logo collection
ambition-billboard-design-for-IT.jpg

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Jenny Henderson Studio is an award-winning brand design and strategy studio for small businesses. Blending artistic instinct with marketing insights, Jenny creates brands that are memorable by design. Based in Toronto and serving clients across Canada, the U.S., and beyond.

© 2017–2026 Jenny Henderson Studio

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