6 lessons learned from building enterprise-level websites

We just wrapped a multi-month journey redesigning the Workers Compensation Board of Manitoba's website — a sprawling digital platform serving everyone from injured workers to healthcare practitioners to employers navigating complex regulatory requirements.  

The experience was often challenging, at times humbling — and overall, a masterclass in why you can't simply scale up your boutique website playbook to tackle enterprise-level complexity.

Listen kids, this isn’t our first rodeo. Our experience ranges from single page scrollers to… well, this. But for our latest in a long line of website projects, we decided to document some key tips and takeaways. For your benefit, should you be looking to embark on the same journey.  

(And if we’re being honest, for our benefit as well. Reflection’s a good thing.) 

Defining enterprise-level: Size isn’t everything

Before diving into the lessons, let's establish what we mean by "enterprise-level" websites. This isn't about page count or budget size — it's about complexity and consequence.  

Enterprise websites are digital hubs for (usually) large organizations dealing with high traffic, multiple distinct user journeys, and complex operational needs. They serve vastly different audiences who arrive with completely different goals, seeking differing information, and expect tailored experiences.

Think beyond the traditional corporate brochure site. Enterprise websites are living, breathing platforms that must simultaneously educate, transact, inform, and guide — sometimes within the same user session.  

Lesson 1: Content is not your enemy (but you’ll think it is)

When you embark on your enterprise-level web build, you may feel like content is trying to kill your project. Not the creation of it — in fact, website projects of this scale often involve culling, not creating, content.  

The bigger obstacle here is the sheer organizational complexity of managing content across multiple departments, each with their own priorities, writing styles, and approval hierarchies.

Operationally, complex organizations have departmental divisions — by necessity, based on objectives, subject matter expertise, audiences, etc. However, these divisions tend to manifest in those organizations’ websites, resulting in a number of fiefdoms of information, architecture, and approvals.

This isn't just project management.
It's psychological strategy. 

Want to drive yourself crazy? Take the traditional approach of creating one massive content document and circulating it for review.  

For enterprise-scale web projects, we find it best to compartmentalize content into individual subject-specific documents; then, to share those via a master document with embedded links to each. This nested approach allows our clients (and their internal stakeholders… more on this in a second) to focus on their specific domains without getting overwhelmed (or derailed) by the broader scope.  

This isn't just project management — it's psychological strategy. 

Lesson 2: Analytics aren’t everything (or, ‘Data lies’)

Every enterprise website project begins with the same ritual: Analyzing existing site analytics to understand user behaviour and popular content.  

It's logical, data-driven… and often completely misleading.

Analytics tell you what happened on your current website (you know — the one you’re redesigning), not what users actually need or want. If critical information is buried six clicks deep in an outdated navigation structure, it won't show up in your ‘top pages’ report. That doesn't mean it's unimportant — it means your current site is failing users.

Site analytics are logical, data driven…
And completely misleading.

So, use analytics as an input, but not the definitive guide. Combine data with strategic thinking, user research, project objectives — and crucially, deep client collaboration — to map out your new site’s structure. 

Lesson 3: The knowledge transfer challenge

Lest you think we’re doing all the heavy lifting in an enterprise-level website project — please pour one out for our client-side project managers.

In our (considerable) experience, the internal team member responsible for managing these projects is often brilliant at project management – but they’re almost never web development specialists.  

By contrast, their internal IT team counterparts are technical wonks, but may not grasp organizational content strategy, or user experience priorities. Their leadership and executive sponsors are at the other end of the spectrum — big on organizational outcomes and alignment, but not so much on the detail. And somewhere in the mix are their colleagues in different departments, whose priority is (rightfully) their own department’s information, preferably shared their way.

Remember those internal clients we mentioned earlier? They’ve entered the chat.

The role of an agency amongst internal clients

Our role as an agency partner isn't about choosing sides or playing favourites — it's serving as a translator and facilitator throughout the process.  

This means asking what might seem like obvious questions to ensure (not assume) everyone’s on the same page; explaining technical concepts without condescension; and standing shoulder to shoulder with our client as they manage their own clients’ expectations.

It’s also about creating space for our clients to admit when they don't understand something. Because between our account managers, creatives and web developers, we’ve got someone who can clear up anything.  

And because uninformed clients can unintentionally make poor decisions that derail timelines and budgets. Good for them, good for us. 

Lesson 4: Why linear thinking can fail

Here's a fun wrinkle in enterprise-level website project management: the linear order that users follow to experience your website has absolutely nothing to do with the logical order for building that website.  

It’s helpful to understand how developers ‘beautiful-mind’ your web design. They think in terms of functional dependencies and future flexibility. They build components that can be reused across multiple sections, establish data structures that accommodate future changes, and prioritize features that unlock broader capabilities.  

This means sometimes building the contact form functionality before finalizing the contact page copy. Or establishing the news section architecture before even looking at any news article content.

Friendly reminder: Trust the dev team

The key insight: trust your agency’s development team (along with their new friends in your IT department) to sequence work for maximum efficiency and future adaptability. Fight the urge to demand linear delivery that matches user experience flow.  

This doesn't mean giving up project oversight — it means understanding that technical sequencing often serves long-term project goals better than logical sequencing. 

Lesson 5: Things change, so let developers plan for it

The best enterprise websites aren't just built for current needs — they're architected for anticipated and unknown future requirements. Skilled development teams think several steps ahead, building systems that can accommodate requests that haven't been made yet.

This forward-thinking approach manifests in seemingly-simple decisions that have profound implications. Choosing content management structures that support multiple content types, building database relationships that allow for complex filtering, creating modular design systems that can expand without breaking — these aren't technical niceties, they're business necessities.

Six months after launch, when stakeholders inevitably request new functionality, well-architected sites can accommodate changes quickly and affordably. Poorly planned sites require expensive rebuilds for minor modifications. 

Lesson 6: Partnership is an imperative

Perhaps the most crucial lesson: enterprise website success requires true partnership, not vendor relationships. The organizations capable of tackling enterprise-level projects aren't just web shops with bigger teams — they're full-service agencies that understand business strategy, content planning, marketing objectives, user experience design, and technical implementation as interconnected disciplines.

Selecting the right partner (an overused phrase that really applies here) matters. Because enterprise websites aren't technical problems with creative wrapping — they're strategic business initiatives that happen to be delivered through web technology. The questions that determine project success aren’t "Can you build this?" — but "Why should we build this?” and "How will this serve our broader organizational goals?" 

Ready to build your enterprise (website)?

You know that saying, ‘nothing worth doing is easy’?  

Enterprise website projects are complex, rigorous, and time-consuming. And that’s if they’re managed efficiently. But the complexity that makes these projects challenging is the same complexity that makes them transformative for organizations ready to invest in doing them right.

If you’re staring down the year-long path towards a new (or renewed) enterprise-level site, we can help navigate the course. At Show and Tell, we've charted these waters before.  

Book a FREE discovery call today.