Upgrade Their Web, Grow Your Biz: Outreach Tactics for Developers

As a developer, it can be headache-inducing to see a website living in the early 2000s. With just a few simple changes and uses of your expertise, you know that you can transform businesses stuck in the past. Each one of these websites just so happens to be a potential client So, what would happen if you turned this pet peeve into a profitable start-up? The barrier likely isn't your skillset, because if you can recognise the problem and consider a solution, you already have an attractive product to sell. The real struggle is getting the owners of these dated websites to give you the time of day to pitch, never mind begin to do the work.

Outreach is more than cold calls and emailing; it requires a strategy built for optimal results. It starts with identifying weak spots in the digital ecosystem and ends with signed contracts and completed projects. This guide walks you through the outreach process step by step, from finding sites that need help to turning those leads into clients.

1. Identifying Outdated Websites

The first step in growing your web dev side hustle is to identify the websites that are falling behind the curve. Perhaps you have collated a list of websites during your search journey online already, or maybe you hit a jackpot of businesses that generate consistent income but stay stuck in the past with the non-user-friendly setups. A site doesn’t need to be completely broken to be considered outdated, as typically, it’s subtle: an old-school layout, sluggish load times, or a site that collapses on mobile devices.

To start, use what you know. Browse your local directories (as businesses that are old school usually prefer working with someone local), and even search through marketplaces. Look out for the basics such as:

Non-responsive layouts that don’t adjust to phones or tablets
Outdated fonts, styling, and Flash-based content
Lack of SSL (i.e., the site still uses HTTP instead of HTTPS)
Visual clutter, inconsistent branding, or hard-to-read layouts
Broken links, missing images, and content that hasn’t been updated in years

Some tools can help you dig deeper. Use services like BuiltWith or Wappalyzer to see what stack a site is running on. If you see outdated CMS versions, old JavaScript libraries, or deprecated frameworks, you’ve found a prime candidate to get in touch with.

2. Researching Potential Clients

Before you even consider pressing send to a quick formulated email with zero depth, take some time to understand who it is you’re getting in touch with. Some research into the business and its objectives will go a long way, especially if you can convey your interest in what they do. Keeping the message personal and relevant will earn you far more brownie points than boasting about what you can do for their website.

Do a deep dive into the business's LinkedIn pages, the meet the team pages, and their key initiatives as stated on their website. Are they a local shop? Or perhaps a long-established London immigration solicitors trusted by all the locals? What makes their business unique, and how would a better website elevate their success?

As much as you may feel like you’re selling your services, that’s not how to view it. You need to sell them the outcome and the potential benefits that will come with upgrading their sites. If they’re customer-centric and need to drive online conversions, mention design features you’d like to include as a top-level focus. If, as mentioned, they’re an immigration lawyer, discuss the integration of review platforms such as Trustpilot, and how essential building trust is from the moment the user lands on the website. Use what you learn to speak their language and frame your services as a solution to their problems, not just a technical upgrade.

3. Crafting the Outreach Message

Once you've gathered all of the relevant information, keep it short, simple and most importantly, personal. You don’t want to send bulk content which will likely be skipped over. Make the key points concise, and clear and leave them wanting to know more.

Start with a quick introduction: who you are, what you do, and why you’re reaching out. Then, bring out what you’ve found on their website. Possibly mention competitors, but only if it's clear who their direct competitors are.

Next, outline the value you can bring. Don’t just say, “I can redesign your site.” Say how that redesign could make their business faster, more user-friendly, and more effective at converting visitors into customers.

End with your CTA (call to action), prompting them to get in touch to find out more.
Here’s an example:

Hi [First Name],

I came across your site while researching [industry or niche], and I noticed that it doesn’t adjust well on mobile screens, which can affect user experience and search rankings.
I’m a web developer who helps small businesses modernise their online presence. If you're interested, I’d love to offer a quick, no-strings-attached audit of how your site could perform better—and how that could translate to more leads or conversions.

Let me know if you’d like to connect.

Best,
[Your Name]

4. Showcasing Your Work

If they bite, be ready to show them you’re the real deal. A good portfolio isn’t just a collection of links—it tells a story. Focus on outcomes. Before-and-after comparisons are powerful, especially when you can explain what changed and why it mattered.

Even better: back it up with data. If a past client saw a 40% drop in bounce rate or doubled their form submissions after your redesign, lead with that.

Here’s what to include in a strong portfolio:

• Screenshots of past projects, ideally with context or short case studies
• A summary of what problems the old site had and what you improved
• Metrics if available (faster load times, better UX, increased conversions)
• Testimonials or quotes from past clients (if you’re starting, ask a friend to create fake testimonials, not by the books but it’ll get you the business)
• A short blurb about your process—how you approach projects, communicate, and deliver results

Host it on your own domain if possible, and make it easy to navigate. You want them to say, “This person knows what they’re doing,” within 30 seconds.

1. Handling Responses

Once your outreach is live, responses will start trickling in. Some people will be interested right away. Others will need more info. Some won’t reply at all.

Here’s how to handle each case:

Interested: Respond quickly. Be clear, confident, and organized. Set up a call or meeting. Have your pitch ready but listen more than you talk.

On the fence: They might ask for pricing or examples. Point them to your portfolio, offer to do a quick audit, or explain how you’ve helped similar businesses.

No reply: Follow up once—just once. Wait about a week, then send a short message to see if they had a chance to look over your offer. If you don’t hear back after that, move on.
Rejection: Stay gracious. When one door closes, another one opens, so rest assured that you will work with the people best suited to your interests and skill set.

Staying professional is key. Especially when so many businesses share the people they work with with other clients and professionals. Even if you face rejection, the same client can come back to you seeking your services years later, just because you came across so well and stuck in their minds.

Conclusion

Most businesses don’t know how much their outdated website is costing them. As a developer, you have the experience and knowledge to offer them a solution, but this can be difficult, especially when they don’t recognise it as an issue.

Your outreach process shouldn’t offend them (or make them feel as though you’re looking down on their current setups). Follow the ‘negative sandwich’ approach. Start with an introduction and how you can see they're leaders in their industry, highlight the issues you’ve spotted, and then discuss the importance of a website built for UX, and how you can help them achieve this.
Build your list of target businesses, create your tailored messages, and wait for the responses. One response out of 100 can be one of the most lucrative sites you work on, so stay consistent and the results will follow!