Cockroach Labs has been working on developing its brand identity, focusing on creating a brand voice that aligns with its mission to "Make Data Easy." Despite the challenges, the design team has embarked on a journey to refine their brand through visual experimentation, particularly using blog illustrations as a platform to explore and evolve their brand voice. Over the past eight months, they collaborated with over 25 international illustrators to produce more than 40 illustrations, which have enhanced social media engagement and community feedback. The approach involves using literal representations, clever storytelling, and thoughtful metaphors to convey technical concepts and cultural stories, leading to significant insights about audience connection and brand identity. The initiative demonstrates the importance of exploration and adaptability in brand development, paving the way for further refinements in visual design, typography, and color. While the brand journey is ongoing, the team remains agile and optimistic about achieving a cohesive brand identity, acknowledging the contributions of illustrators who have propelled their design efforts forward.