How entrepreneur Jenell B. Stewart uses ConvertKit automations to grow her community

Case study Email Marketing
7 min read

Ten years ago, Jenell B. Stewart started a blog and YouTube channel documenting her natural hair journey.

Today, she’s a powerhouse entrepreneur helping aspiring creators and brands build their businesses on social media and beyond.

Jenell runs her business remotely, working with major brands from Nissan to Kami Cosmetics.

With over 145,000 YouTube subscribers and more than 100,000 followers on Instagram and TikTok, she’s turning all the lessons she learned building her blog into programs for others. “I’m a digital entrepreneur through and through,” says Jenell. “It’s all about helping people setting up their podcasts or getting the support they need to create for a new audience.”

Jenell's revenue breakdown.

In addition to social media, podcasting, and vlogging, Jenell created a series of courses and a community called Content Confident designed to help aspiring creators achieve the same success.

Because social media and her products take up so much of her energy as a full-time content creator, she largely automates running her 5,000-strong email list — setting up a series of automations through ConvertKit that allows her to focus on growing her business without losing performance. “I’ve sent out more than 4 million emails, and my open rate is still 25%,” she says.

How Jenell B. Stewart greets potential Content Confident members on her website.

Here’s how she automates her email nurture flow so that 90% of her new community members come from the channel.

Email holds the entire marketing funnel together

Email serves as Jenell’s focal point for the rest of her activities, whether participating in events, releasing her latest podcast episode, or launching something new. “I keep my audience updated on all things Jenell and what my business is doing,” she says. “I use email to communicate about the ins and outs of all of my programs, send them freebies or perks, offer support, and to sell and nurture my audience.”

“The biggest way I use email is to nurture a community,” says Jenell. “Instagram isn’t mine. If it crashed tomorrow, I would pretty much lose my entire brand. That’s why it’s important to spend time building up your email list.”

Jenell’s opt-in form is powered by ConvertKit.

While Jenell has her hands in all kinds of products, it’s her online community that’s the focus of her latest campaign. She put together a multi-stage automation that takes her email list from new subscriber to community member in just 23 days.

Here’s how the funnel works:

1. Start with a freebie

“My goal for the entire funnel is to get them to sign up to my membership community, and that starts with my crash course, which is a free five-day email-based video course all about content planning,” says Jenell. “I want people to get started with something that builds their confidence, and planning content can be really overwhelming. This is the first step toward seeing the value that they can get out of my community.”

The Crash Course covers key fundamentals of content planning that sets students toward a path toward community membership.

Once someone starts the free course, the clock starts on the sales cycle for Jenell’s full content community. To create a sense of urgency — and add a little extra oomph with a discount — Jenell sends a daily email. “I make sure I’m communicating what they’re supposed to be learning each day of the crash course,” she says. “Each email reminds them they only have limited access and that there’s an upsell option to upgrade into the full community.”

ConvertKit makes it easy to build detailed automation sequences.

All of these emails are automated using ConvertKit. Says Jenell, “With ConvertKit I can do the entire sequence, from the landing page that gets them to sign up to getting them through the entire crash course.”

2. Create a welcome flow

Once you’ve delivered that freebie, you need to welcome your new subscribers into the fold. “You don’t want to just give the freebie and have it go nowhere,” says Jenell. “You just did all the work to create the freebie and you need to utilize it. Automations help me do that.”

Immediately after the course ends, anyone who hasn’t signed up for the community receives a six-email welcome series inviting them into the program and extending that early bird discount.

Jenell’s automation starts with the latest email in her newsletter, so that she’s delivering on her promise to any new subscribers with fresh content.

Because anyone new in the flow has recently taken the crash course, they’re primed for a harder sell. The time is now, just when subscribers are super motivated and inspired from the course, to capitalize on that intent. “I want them to be excited about content creation,” says Jenell. “I build that anticipation, give them a discount to entice them further, and then use several emails to offer testimonials that speak to the value I’m creating.”

3. Keep the conversation going

Once that flow is complete, the automation waits three days before regrouping. From there, Jenell sends a fifteen-day automation that continues to nurture potential members. “I’m priming them to become members of Content Confident, essentially,” she says. “If they’re not going to convert right away, then I back off a little and focus on value. I don’t actually talk that much about membership at this point in the sequence. It’s more about highlighting pain points and how I can help.”

After the first five days, the nurture flow focuses on tips and advice.

At this point, it’s all about keeping the conversation moving forward, so potential members see the value in signing up and want to hear more of Jenell’s advice. She rotates topics that all relate to membership, like how to plan for success, how to manage stress as a creator, and highlighting current member stories.


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A post shared by Jenell B Stewart (@jenellbstewart)

An example of the kind of motivational videos Jenell includes in her email sequence.

This includes a few more free pieces of content, like a social media checklist, a Q&A video, and a link back to archived Instagram Lives just for subscribers. The goal of this section of the nurture flow is not just to get sign ups, but to start conversations and help others grow. “It’s all about encouragement and welcoming them into the larger community,” says Jenell. “I actually tell them to hit reply and ask me a question based on the email. I want to hear from them. I always reply back if they do.”

All this adds up to training subscribers on a certain email cadence — even if those emails aren’t sent in real time. “I’m building the habit that I’m going to be sending emails on a regular basis, and that you should open every single one because it’s going to add value,” she says. “I made these automations almost a year ago, and they continue to work for me now because people feel connected, like I’m talking to them. It’s what builds trust and loyalty in the long run.”

Automations give freedom to focus on community

“Anyone who wants to do email marketing knows that creating emails on a regular basis is difficult and time-consuming. With ConvertKit’s email automations, I can create emails once and they can continue to work for me and my business,” says Jenell. “I don’t have to be part of the equation to keep things running.”

ConvertKit’s Automations give creators the freedom and flexibility to work on their businesses instead of working in them. With visual automations, you can build custom paths for your funnels by connecting events, actions, and conditions. When joined together, these elements create your subscriber’s journey in one easy-to-understand and totally customizable process.

“I still have work to do, but I can focus on what excites me,” says Jenell. “You know, people say ‘Make money in your sleep,’ well, this helps me do exactly that.”

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Kayla Voigt

Always in search of adventure, Kayla hails from Hopkinton, MA, the start of the Boston Marathon. When she's not using words to help businesses grow, she's probably summiting a mountain or digging into a big bowl of pasta. Like what you're reading? Come say hi:

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