5 Fatal Mistakes Companies Make When Sticking With WordPress or Drupal Too Long

The Legacy CMS Trap

INTRODUCTION: Welcome to the Legacy CMS Trap

There’s a silent problem killing your digital marketing ROI. You don’t see it at first: your site is live, traffic looks decent, and the dev team swears everything is working. But deadlines are slipping. The marketing team is frustrated. Campaigns are stuck in a backlog. And when someone finally uncovers the root of the issue, it’s this: you’re still using a legacy CMS.

For years, platforms like WordPress and Drupal were the default for everyone from the local coffee shop to Fortune 500 enterprises. Open source is endlessly customizable, widely adopted, and oftentimes free. But today, those same platforms are dragging teams down. Slow rollouts. Technical debt. Plugin chaos. Security patches. Fragile integrations. And worst of all, an entire marketing team blocked by a technical gatekeeper to launch a new landing page.

We’ve seen this happen over and over — and it’s not just a “tech issue.” It’s a business growth issue. One company we worked with had a marketing team of 12 and 1 full-time developer. Every email campaign, product update, webinar, landing page, or blog post had to route through the single developer because their WordPress site was so heavily customized with a decade's worth of custom features and plugins. Every update took days or weeks to launch. In one case, this meant a landing page never launched in time for a last-minute conference speech by the CEO.

But after helping them migrate to Squarespace, everything changed. Time-to-publish dropped from days to minutes. The sole developer was able to focus on higher-value work that actually needed customization. Campaigns rolled out 3x faster. Most importantly, their cost-per-lead dropped 37% in the first 90 days.

Over time, we’ve identified five common mistakes companies make when they remain on legacy CMS platforms for too long. We’ll show you a step-by-step modernization framework, highlight common objections from internal stakeholders (and how to address them), and provide you with the roadmap you need to confidently make the switch, without compromising SEO, speed, or sanity.

THE MYTHS: What We’ve All Been Told (That’s Now Outdated)

Let’s be clear: WordPress, Drupal, Joomla, and many more open-source CMS platforms had their time. However, what was once a flexible advantage has now become a fragile liability. Here are some of the most persistent (and damaging) myths keeping companies stuck:

Myth #1

“Open Source Gives Us More Control”

Yes, technically. But with control comes responsibility. Maintaining dozens of plugins, hand-coded templates, security patches, and legacy modules is a full-time job. And guess what? Most teams aren’t doing it well. That control often ends up controlling and hindering you.

Myth #2

“Squarespace Is for Bloggers or Small Sites”

That was once the case, but Squarespace has since evolved. It now powers global brands, multi-location businesses, and enterprise portfolios. It’s scalable, secure, and marketing-friendly. You don’t need 50 plugins to get a beautiful, fast, mobile-optimized site that fits your brand.

Myth #3

“Squarespace Is Too Simple”

What your team needs is freedom, not complexity. They need to launch a new campaign on Friday without pinging IT or worrying that deploying on Friday breaks something that won’t get fixed until Monday morning. Squarespace delivers structured flexibility: fast, secure, and proven workflows tailored to your brand.

Myth #4

“We Already Invested Too Much to Switch Now”

That’s sunk cost fallacy. The longer you stay, the more you’ll spend maintaining it. You’re already leaking budget through developer time, lost productivity, delayed launches, and bloated infrastructure. Migration is cheaper than stagnation.

THE MECHANICS: A 5-Step Plan to Modernize Without Breaking Your Business

Here’s the step-by-step framework we use to help clients migrate from WordPress or Drupal to a modern system like Squarespace:

Step 1

Audit Your Current CMS Bottlenecks
Look at: How long does it take to publish new content? How many hours are spent on updates? Plugin bloat and technical debt. Performance (load times, etc.).
Use a tool like Google PageSpeed Insights to view your website's performance score. Remember, performance is a ranking signal to Google.

Step 2

Identify Core Marketing Needs
What are the must-haves? SEO control? Campaign landing pages? Integrations with email, analytics, or CRM? Multi-user roles or approval workflows?
List out your essential features before you build anything.

Step 3

Set Up Squarespace the Right Way
Choose a template with a modern structure and a fast load time. Customize global styles and brand kit. Set up URL redirects to preserve SEO. Connect integrations (Zapier, Mailchimp, Google Tag Manager, etc.). Bonus: Add team-specific dashboards and permissions so your marketing team doesn’t break anything.

Step 4

Design a Migration Map
Map content types from old CMS to new. Set priorities: homepage, product pages, blog, forms. Use tools like Slickplan or MindMeister to build your sitemap, content structure, and ideal user journey.

Step 5

Test, QA, Launch
Before going live: Run Lighthouse audits. Validate mobile responsiveness. Set up 301 redirects. Test forms, workflows, and CTAs. Schedule a soft launch or beta test for internal teams

Results

Within weeks, most teams report:
50–70% faster content and campaign deployment | Lower bounce rates and faster site speed | Higher team morale (yes, really) | A significant bump in ROI

MAINTENANCE: Keeping Things Fast, Simple, and Scalable

The beauty of moving to Squarespace lies in its simplicity. But simplicity doesn’t mean “set it and forget it.” Here’s how to maintain high performance:

  • Monthly content reviews — Update CTAs, test messaging, refresh visuals

  • Quarterly integrations check — Make sure your CRM, email platform, and analytics are syncing properly

  • Team Workflow Audits — Is Marketing Still Agile? Are your developers still unburdened with basic web work and able to be more productive?

  • SEO tune-ups — Revisit site structure, meta tags, and internal linking

  • Conversion testing — Use Squarespace’s native analytics or tools like Hotjar to see what’s working

Now that you’re no longer faced with bottlenecks from waiting on IT for updates, launches, or analytics, you can focus on continuous improvements to see results faster.

Escape the Trap Before It Costs You More

If you’re still running your site on WordPress or Drupal, and your marketing team is waiting days (or weeks) to launch, your CMS is killing your opportunities.

You’ve now seen the five fatal mistakes that companies make by staying on legacy platforms too long. You’ve seen how campaign delays, bloated plugins, and development bottlenecks chip away at your ROI, speed, and sanity.

This is your chance to make it right.

Berry Buckley specializes in helping organizations migrate from legacy content management systems (CMSs) to a modern, high-performance Squarespace stack built for speed, scalability, and autonomy. No guesswork. No broken templates. No SEO loss. Just a clean transition, handled by experts who’ve done it before.

So here’s what to do next:

👉 Book a discovery call. We’ll audit your current CMS setup, identify friction points, and develop a custom migration plan tailored to your needs.

👉 We handle the migration. Your team stays focused while we move everything.

👉 You go live and make changes faster. No more waiting on developers. No more campaign delays. Just clean, high-performing pages that let marketing move at the speed of growth.

This isn’t just a website upgrade — it’s a marketing unlock.

Don’t waste another quarter patching plugins or working around broken workflows. Let us help you break free from the legacy CMS trap — and build something that works for your team, not against it.

Your next campaign deserves better. Let’s build the platform you deserve.

TROUBLESHOOTING

Common Objections and How to Overcome Them

“But what about our custom features?”

If it’s truly mission-critical, consider keeping those parts on a subdomain or integrating through APIs. But 95% of what you’ve customized can be simplified or replaced with built-in tools.

“Won’t we lose SEO?”

Not if the migration is handled properly. Preserve the URL structure, use 301 redirects, and optimize metadata. In many cases, improvements in speed and structure boost SEO after migration.

“Our dev team prefers open source.”

That’s understandable. But the goal isn’t to keep developers busy, it’s to free them up for higher-value work. Let marketing run campaigns without waiting on code deploys. You can finally make site changes on a Friday without worrying throughout the weekend.

“We’ve already invested too much.”

That’s the cost trap. Migrating now reduces long-term maintenance costs, lowers hosting expenses, and increases campaign ROI. It pays for itself in months.