Dropbox · Apr 2020 – Apr 2023

Dropbox: Content design strategist

Led a complex migration of 500+ help articles to a new Contentful infrastructure, the foundation for an intelligent, contextual help system.

Role
Content design strategist
Client
Dropbox
Year
Apr 2020 – Apr 2023
Practice
Content design • In-product UX • Content migration • Governance

Case study: In-app contextual help for Dropbox support content

At Dropbox, I led a complex content migration initiative transforming their enterprise help system, which had grown unwieldy and inflexible within Adobe Experience Manager.

The existing system struggled with content discoverability and maintenance, limiting our ability to serve Dropbox’s diverse user base across different subscription tiers and roles.

The migration was designed as a multi-phase project, starting with comprehensive content audits and technical requirements gathering, moving through careful content modeling and governance planning, and culminating in the migration of 500+ help articles to a new Contentful infrastructure.

This foundation would ultimately support an intelligent, contextual help system that could deliver the right content to the right users at the right time.

Dropbox Business interface with a Recommended help panel surfacing contextual articles
What the customer sees

01 / Migration strategy and expertise

  1. Content discovery & planning
    • Comprehensive content audit and mapping
    • URL structure analysis and catalog
    • Identification of redundant content
  2. Technical migration management
    • Structured data mapping approach
    • Media asset handling procedures
    • SEO preservation through 301 redirects
  3. Content model optimization
    • Developed user-centric content architecture
    • Created efficient authoring workflows
    • Established clear governance procedures
Content model tables defining elements for Landing, Search, and Article surfaces
Content modeling for key areas of the new CMS (Contentful)

02 / Risk mitigation strategies

  • Comprehensive pre-migration content audit
  • Detailed content mapping documentation
  • Thorough testing protocols
  • Clear rollback procedures

03 / Key achievements

  • Zero content loss during migration
  • Maintained SEO rankings through strategic redirects
  • Improved content accessibility through structured taxonomy
  • Enhanced user experience through better content organization
Field validation, settings, and appearance configuration for the new content types
Rule setting for content display types