Platform Modernization

Customer-Facing Site Modernization

Migrated two high-traffic customer sites off WordPress and a deprecated IE rendering engine — without breaking a decade of existing installations in the field.

<200ms Page load (from 1–3s)

650K+ Preparers on updated platform

1M+ Daily requests migrated

9 yrs Backward compatibility preserved

Context

Two customer-facing sites used by ~650K tax preparers ran on WordPress and were embedded in Drake Tax Desktop through an end-of-life Internet Explorer rendering control. Page loads took 1–3 seconds, the app generated over a million requests per day, and every content update required a CMS. The IE engine mangled modern CSS and had no path forward.

Role

Led the full migration — business case, epic decomposition, technical architecture, test coverage, and content-editor enablement. Owned the decision sequencing from back-end signal through UI, and carried the work through human and AI code-review rounds.

Challenge

A decade of older Drake Tax installations had hard-coded URLs pointing at these sites. Any migration that broke those references would silently fail for users who never updated — an unacceptable backward compatibility risk. The release path also needed to stay clean for QA, who couldn't validate against a test environment without a custom build.

Approach

Built a business case comparing Azure and AWS hosting, then decomposed the work into an epic of independently shippable stories — configuration, polling, browser migration, typography, and refresh behavior.
Treated backward compatibility as a hard constraint: published nine archive mirror years so a decade of older desktop installations with hard-coded URLs keep working unchanged.
Replaced WordPress with a lightweight static-site generator (Markdown → CDN) reducing page loads from 1–3 seconds to under 200ms.
Built a configurable URL system and a fail-safe background metadata poller with interval floors — preventing a content typo from stampeding the CDN under production load.
Migrated the embedded browser from the deprecated IE control to Chromium-based WebView2 with a runtime-missing fallback and an HTTP/HTTPS allowlist hardening against injected links.
Turned publishing into a self-service, version-controlled workflow — technical writers ship via pull request in minutes instead of through a CMS.

Two liabilities removed from the release path — WordPress and end-of-life Internet Explorer — while preserving backward compatibility for every version ever shipped.