Home Ideas Why your first website works until it doesn't

Why your first website works until it doesn't

Your scrappy starter site got you this far—but now that you're growing, it's probably holding you back more than helping you move forward.

Your first website was good enough to launch your company. It told your story, showed people what you do, and maybe even looked great. If you built it yourself on a platform like Squarespace or Wix, it might have been surprisingly easy and cheap.

Now that you’re well past the launch stage, you have more clients, more revenue, a bigger team. Your site still “works” in the basic sense — it’s up, it’s on-brand, and people can find it. But because of how it was built, it’s holding you back.

When your website becomes more of a roadblock than a launchpad for your marketing ambitions, you need a new, more scalable site.

What breaks as you grow

Websites start failing to scale in the same way that Ernest Hemingway once described what it’s like to go bankrupt: gradually, then suddenly. But the reasons why those sites break are encoded into their DNA.

For starters, basic websites are almost always built one page at a time. This makes sense — after all, people experience websites one page at a time, and pages are also how we experience and create printed material. Naturally, user-friendly web design tools adopted the page as their number one mental model. Need a blog post? Build a page. Need a landing page? Build another page.

While this approach is fine for a small site, you can easily imagine how it can become a hindrance as a site grows. Need ten feature pages? Copy and paste ten times. Need to change a product or service name that’s mentioned all over the place? …uh-oh.

Another breaking point is collaboration. Web pages look like documents, and so you might expect editing them collaboratively to be as free and easy as opening a Google Doc. Sadly, almost no web publishing platforms have that level of multiplayer collaboration — some, like Webflow, don’t currently even let two people have the site open at the same time. Waiting your turn to edit something, like schoolchildren at the drinking fountain, is a major momentum-killer.

Lastly, early-stage sites usually have to make hard tradeoffs between reliability and customization. A site you set up quickly and easily on a fully managed platform like Squarespace will be rock-solid at scale, but nearly impossible to customize beyond a few color and font choices. Or, if you went for a more customizable platform like WordPress, but didn’t invest in future-proofing your theme setup, plugins, or hosting, your site may look fantastic but be slow, insecure, and prone to breaking down.

You can’t hack your way to scale

There comes a day when a site that worked fine no longer really works. Maybe the performance tanks under traffic spikes. Maybe the content is out of date because it’s too hard to update. Maybe marketing has an idea for a campaign that goes nowhere because there’s nobody available to build what you need to support it.

That’s when the “shadow tech” starts creeping in. Instead of wrestling with the main site for a campaign landing page, you spin it up on Unbounce or HubSpot, or park a PDF on Notion or Drive because it’s easier than getting it into the CMS. Those workarounds help you ship quickly in the moment, but they splinter your brand experience, scatter your data, and increase the risk of broken links.

You should expect both from your second site: enough flexibility for your brand and campaigns, while holding to modern standards of security and availability.

Good things come from structure

There’s a lot to decide when architecting and designing a beautiful, resilient, flexible site that reflects a company and its ambitions, from functional choices like JavaScript frameworks to design aspects like font and color. But I’ve found that what makes the single biggest difference from a marketer’s perspective is shifting the focus from individual pages to structured content.

With reusable templates, components, and variables, you separate what you’re saying from how it looks. You make changes once and have them ripple everywhere they need to go, fitting within a design that a pro came up with and that you don’t have to (and probably shouldn’t) touch. When you need to make bigger changes, you can have someone add new sections, campaigns, and content formats without fully rebuilding.

By carefully choosing the technology to implement this approach, you can also address other challenges. Grown-up CMSes support simultaneous users, so you can edit and post on your own schedule. Modern website stacks, like Sanity + Next.js, are built to be both reliable and adaptable in the hands of a web developer.

Life’s too short for bad websites

You don’t have time to build a new site. You really don’t have time to keep up the old one. It’s an investment of time, effort, and money, and there’s always something more urgent.

But every month you keep the old site, you edge closer to the point where you should have gotten a new site already. The hours and budget spent patching it together, plus the opportunity costs and eroded trust that accrue when it’s too hard to keep things fresh, eventually add up to more than the time and cost of building a new site. It’s never too late, though: the second-best time to start building the website you need is right now.

Websites have a shelf life. Most companies simply need a new one every so often. So celebrate the milestone: you outgrew the starter kit and are no longer scrappy; your brand has earned something beautiful, functional, and scalable. Now it’s time to work with a pro and get it done.

David Demaree

About David Demaree

David is founder and principal at Bits&Letters, a boutique digital agency in NYC. He’s spent two decades shaping design and typography platforms at Adobe and Google, and now helps fast-growing companies build websites that scale with clarity and craft.