How freelancer Brennan Dunn uses more than 100 data points to segment his email audience of 50,000

It’s one thing to build an email list with 50,000 subscribers. It’s another to build a list of 50,000 subscribers who continue to find your content relevant and useful month in and month out.

Brennan Dunn, who runs Double Your Freelancing, a platform that helps freelancers establish and grow their business, has had to learn the difference as his email newsletter gained hundreds of new subscribers over the years. Double Your Freelancing now sends its weekly email newsletter to more than 50,000 people, sharing useful articles, guides and advice with freelancers in a range of industries.

The secret to keeping all those readers happy? Audience segmentation, Dunn said. Segmentation refers to the process of putting email subscribers into various groups that best serve their needs.

Dunn uses a range of data to break his audience into specific groups of subscribers based on what their needs are. Double Your Freelancing then targets specific groups with the content that will be most helpful for them.

Dunn, a recent guest on’s Pushing Send podcast, explained how he goes about gathering data on his audience without being sketchy. For one, Dunn keeps the focus on his audience’s needs. For example, the email newsletter content each subscriber receives is based on information Double Your Freelancing collects from them.

“If I can better understand who you are and what you need from me, I can better serve you.”

“I do a lot of aggressive data collection with the intent of telling people, ‘I want to better serve you,’” Dunn said. “If I can better understand who you are and what you need from me, I can better serve you.”

In addition to Double Your Freelancing, Dunn is the co-founder of RightMessage, which has helped more than 10,000 customers segment their audience based on subscriber needs.

Here’s how Dunn executes on data collection for Double Your Freelancing, and his advice for email marketers looking to learn more about their audience.

Start with a survey

Anyone who visits the Double Your Freelancing website receives a survey prompt with a series of three questions. The last step in the question series asks the visitor to enter their email address to get an email with tips and advice related to problems that person faces. That short interaction gives Dunn and his team the first data points through which he can segment his audience.

Dunn noted anyone with a website can apply this technique. The goal is to ask a series of short (but specific) questions that help give you insight into their lives and work. Specifically, Dunn asks first-time visitors what kind of work they do and if they’re full- or part-time freelancers. In total, he uses roughly 100 data points to help him group his email subscribers.

He collects info on “everything from what kind of work they do to what kind of content are they reading on my site to how they are engaging with my automated newsletter,” Dunn said.

Keep asking questions

Once you land a new subscriber, Dunn suggests following up with another question or two—anything that helps you get a clearer picture of the help they’re looking for.

“That could be an email saying, ‘Hey, I want to make sure I have a really good roster of feature content I’m working on for you,’” Dunn said. “‘Reply to this email with a sentence or two about your business and how I can help you.’”

A simple follow-up can lead to important feedback and spark a one-on-one dialogue, he said.

Track click-throughs

Like most content producers, Double Your Freelancing puts a lot of emphasis on tracking which articles and guides subscribers are getting traffic. Dunn takes that data a step further by using it to segment his subscribers.

“If you’re on my email list and you read five articles on my site, five of those segmentation data points are going to be sent up in the background,” he said.

Know that this is a long-term strategy, especially if you’re just getting started creating content. (Dunn estimates Double Your Freelancing has roughly 9 years worth of evergreen content ready for readers.) The important part is to get into the habit of not only tracking what people are reading, but using that information to categorize different types of users, Dunn said.

Find Leads. Keep Leads. Convert Leads.

Cultivating relevancy through content.

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