Case Study: Transforming a legacy brand into a modern learning platform

Repositioning O'Reilly for enterprise growth

The O'Reilly website & brand when I joined in fall 2017

Challenge:

O’Reilly was a beloved but aging tech brand, best known for its iconic animal-covered books and elite technology conferences. Like the technologies it chronicled, O’Reilly had a history of reinvention. Its next transformation was bold: shifting from a publisher of print books to a digital learning platform designed for enterprises to upskill their tech teams.

This transformation came with multiple challenges:

A new customer segment: enterprise teams rather than individual consumers.
A new product model: subscription-based learning, not one-off book sales.
A marketing team and tech stack built for direct-to-consumer e-commerce, not enterprise sales.
An iconic brand that, while admired, looked dated and fragmented across conferences, books, and its learning platform.

Solution:

We rebuilt the marketing organization to align with the new strategy—hiring talent, overhauling the marketing tech stack, and expanding capabilities to reach enterprise buyers.

For the brand, we took a cautious but creative approach. Research confirmed O’Reilly’s brand still carried immense prestige with customers, authors, and contributors. The iconic animal illustrations were beloved, but the visual identity felt stale and inconsistent.

Through collaborative workshops and testing, we modernized the identity:

Preserved the animals to honor brand heritage.
Introduced color to convey energy, inspiration, and growth.
Unified fragmented sub-brands under a single master brand.

We then rolled the new identity out across the full customer journey—from the product UI to marketing campaigns. To amplify the transformation, we launched a tightly targeted Connected TV campaign aimed at technical decision-makers and influencers, sparking fresh evangelism for the brand.

Relaunched branding and website

Book covers were updated to preserve the iconic animal illustrations, but updated with color. Color coding by topic was removed, the cover design simplified, and modernized.

Results:

Authors and customers embraced the new identity immediately, celebrating it on social media with pride and excitement.
Within 24 months, and on a limited budget, aided awareness of O’Reilly as a learning platform doubled among tech professionals.

Successfully repositioned O’Reilly from a legacy publisher into a platform for continuous professional development, renewing its relevance and sparking new growth.