Behind the Build: Ask Media's WordPress Migration
Welcome to WP for ENTERPRISES, where we go behind the scenes of BILLION-DOLLAR WordPress websites.
In this issue, you'll discover:
- Challenges with Ask Media Group’s old CMS setup.
- Why did they choose WordPress?
- 5 key strategies behind their 12-week migration.
- A look inside their new WordPress tech stack.
- Unexpected wins from this large-scale migration.
~4 BILLION-DOLLAR BRAND
When you hear "Ask Media Group" you might immediately think of Ask.com, but this media company is part of IAC—a global internet leader (valued at $4.16 billion as of 2025) that owns brands like Investopedia, verywell, Care.com, Travel + Leisure, and Vimeo.
Ask Media itself manages a diverse portfolio of search and content sites that collectively attract 245 million unique visitors monthly and generate over 500 million unique page views.
Ask Media Group is a billion-dollar company—a perfect fit for this behind-the-scenes deep dive—and a team of over 100 people.
By 2022, Ask Media was facing a critical turning point with their content management infrastructure.
They needed to migrate 11 web properties from their outdated, proprietary CMS called "Arbotron" to something more agile, modern, and future-proof.
The stakes? Maintaining seamless service for millions of monthly visitors while completely rebuilding their digital foundation—all within a remarkably tight timeframe.
WHAT WAS THE PROBLEM WITH THEIR OLD SYSTEM?
Ask Media's legacy CMS Arbotron was becoming a liability rather than an asset:
- Limited Support: Their proprietary CMS had dwindling developer support, making updates and maintenance increasingly difficult.
- Fragmented Management: Each website required its own codebase and review process, creating bottlenecks.
- Outdated Practices: Their aging infrastructure held back SEO performance and accessibility.
- Complex Editorial Workflow: Content syndication across sites was manual and time-consuming.
- Ad Management Headaches: Implementing and managing ads across multiple sites was inefficient.
- Scalability Concerns: As traffic grew, their legacy CMS struggled to keep pace.
- Expensive Page Builders: Reliance on various page builders was increasing costs while support for them expired.
The company needed a modern, unified solution that could handle their massive content library while streamlining operations across their entire digital portfolio.
WHY WORDPRESS?
After evaluating a few options, Ask Media chose WordPress for these 3 reasons:
✅ Open Source Advantages
Always Improving: Open-source means WordPress gets better every day.
Cost-Effective: No licensing fees. Lower total cost. Big value.
Endless Ecosystem: Thousands of plugins. A massive dev community.
Built to Flex: Tweak it, stretch it, make it yours.
✅ Gutenberg Block Editor
Modern Editing: Visual, drag-and-drop. Easy for everyone.
Consistent Design: Structured blocks keep things clean and on-brand.
No-Code Power: Even non-tech teams can build rich content.
✅ Enterprise-Ready
Scales Big: Handles heavy traffic like a pro.
Safe & Secure: Regular updates. Strong security practices.
Fast & Smooth: Optimized for speed and performance.
Plays Well with Others: Robust APIs for easy system integrations.
5 STRATEGIES MADE THIS MISSION-CRITICAL MIGRATION A SUCCESS
Now, let's dive into the 5 strategic approaches that made this ambitious migration a success.
Strategy #1: WordPress Multisite as the Centralized Command Center
Instead of creating 11 separate WordPress installations, Ask Media used WordPress Multisite to consolidate all properties under one roof.
This created a unified dashboard where administrators could oversee content and settings for all sites simultaneously.
This architecture enabled centralized user management and content oversight across the entire portfolio, from Ask.com to Reference.com and everything in between.
Strategy #2: Advanced Content Syndication System
One of the most powerful innovations in Ask Media's WordPress implementation was a custom content syndication strategy.
This allowed editors to create content once and publish it across multiple relevant sites in the network.
The WordPress editor was customized so that content creators could select which sites an article should appear on, making multi-site publishing seamless.
This approach:
- Eliminated duplicate work.
- Ensured consistent content quality across properties.
- Maximized the reach of each piece of content.
- Streamlined the editorial workflow.
This syndication strategy was implemented through custom plugins that extended WordPress's native capabilities, turning their Multisite network into a true content distribution platform.
Strategy #3: Custom Gutenberg Block Development
To preserve the unique features of their old CMS while embracing WordPress's modern editing experience, my team at Multidots developed custom Gutenberg blocks.
These blocks replicated their legacy features while adding new capabilities, ensuring that editors could maintain familiar workflows while gaining new powers.
This meant:
- Rich content like Q&A formats were preserved.
- Interactive modules continued to function.
- Custom layouts remained intact.
- Editors could work within a familiar paradigm.
My team reverse-engineered existing functionalities and rebuilt them as WordPress components, ensuring no functionality was lost during the transition.
Strategy #4: Automated Migration Pipeline
Moving over 50,000 posts from a proprietary CMS to WordPress presented enormous challenges.
My team tackled this with custom WP-CLI scripts that automated the content migration process.
This approach ensured:
- Data integrity was maintained throughout the process.
- All metadata, URLs, and relationships were preserved.
- The tight 12-week timeline could be met.
- Human error was minimized.
The migration scripts underwent extensive testing to ensure that pages, images, SEO elements, and user-generated content moved over without broken links or formatting issues.
Strategy #5: Unified Advertising Management
As a performance marketing company, Ask Media's revenue depends heavily on effective ad management.
Previously, each site handled ads independently, creating inefficiencies and missed opportunities.
During the migration, we developed a bespoke WordPress plugin for advertising that works across the entire multisite network.
This centralized approach:
- Streamlined ad operations.
- Enabled faster ad placements and changes.
- Ensured consistent ad implementation across all sites.
- Maximized revenue opportunities.
The new system made advertising management plug-and-play across all 11 sites, replacing the previously fragmented approach.
INSIDE ASK MEDIA'S NEW TECH STACK
The migration completely modernized Ask Media's technical foundation.
SURPRISING RESULTS & HIGHLIGHTS FROM THE MIGRATION
The migration delivered remarkable results that exceeded even Ask Media's expectations:
- Completed 11 website migrations in just 12 weeks with zero downtime.
- 65% faster page load speeds after migration.
- Migrated over 50,000 posts and associated media using custom WP-CLI scripts and a multi-phase, content-freeze-minimized process.
- Reduced publishing time by up to 70% with custom Gutenberg blocks and reusable patterns.
- Created a centralized editorial dashboard for managing content across 30+ sites (initial 11 + scaled after launch).
- Zero disruption to search engine rankings thanks to careful URL mapping and redirect strategy.
- Custom on-the-fly image resizing and CDN integration reduced media load time across devices.
FINAL THOUGHTS
Ask Media's successful migration offers valuable lessons for any enterprise considering re-platforming.
✅ Consider WordPress Multisite for managing multiple properties efficiently.
✅ Custom plugin and block development can bridge any gaps between legacy systems and WordPress.
✅ Content syndication can dramatically improve publishing efficiency.
✅ Automated migration tools make large-scale content transitions manageable.
✅ Consolidating ad management can improve both operations and revenue.
✅ Partner with experienced teams who understand the complexities of enterprise migration.
P.S. Proud to share that Multidots led this transformation for Ask Media Group. If you're thinking about a similar migration, we can definitely help. Just reply to this email, or contact us.
Want the full scoop? Watch Aslam Multani (our CTO) walk you through the entire migration of Ask Media in this behind-the-scenes video.
IN CASE YOU MISSED IT
By the way, in the previous issue, I shared “The Five Key Strategies Behind NASA’s Migration and Consolidation of 1,000+ Websites to WordPress" Check out this link.
In this issue, you'll discover:
- Challenges of NASA’s legacy web stack.
- Why NASA picked WordPress over 100+ CMS options.
- 5 key strategies behind NASA’s WordPress migration.
- Inside NASA’s new tech stack.
- Fun and surprising facts about NASA’s WordPress journey.
Anil Gupta
👋 Until next time, Anil | CEO and Co-Founder → Multidots, Multicollab & Dotstore.
P.S. I also write about personal growth and agency growth.
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