How to add a high-value newsletter to your existing business

Ever thought about launching your own newsletter?

Maybe one day, you’ll quit your job and build your own newsletter business from the ground up.

Well, you may not have to. If given the right opportunity at the right company, you could build one as a part of your job.

That’s exactly what Jennifer Chou did while working in tech education.

And in less than a year, she built and grew her newsletter to over 60,000 engaged subscribers in a thriving community!

We recently sat down with Jennifer Chou, growth marketer at EntryLevel and co-creator of EntryLevel’s newsletter, Level Up, to discuss how she fast-tracked her audience growth and built a successful newsletter in under a year.

In today’s Creator Spotlight, we will cover:

• How Jennifer leveraged her position, expertise in marketing, and beehiiv to capitalize on the newsletter opportunity.

• The content strategy driving results for the newsletter and the existing education business.

• Experimenting with different growth drivers, partnerships, and other strategies based on audience feedback (and how to collect that feedback).

• Getting started with paid ads and what the next few months look like.

Let’s get into it.

Interested? Subscribe here:

EntryLevel: A Unique Model for Online Tech Courses

Jennifer’s story begins with her workplace: EntryLevel.

She shared, “I’m currently the growth marketer at EntryLevel, which is separate from our newsletter. EntryLevel is an online education business, and we teach people tech skills like product management, UX design, digital marketing, data analysis, venture capital analysis, and many other tech skills.”

EntryLevel stands out in the online course space by offering a unique model: you pay for a course but get your money back if you complete it on time.

While this may seem like a strange business model, it works well. EntryLevel can boast 40% course completion rates, while the average online course only gets about 2% completions. This means their students are actually learning and benefiting from the programs they offer. Ultimately, EntryLevel can help anyone in tech improve their skill sets, land better jobs, and accelerate their career.

The Level Up Origin Story: Zero to 60,000 Subscribers

As the growth marketer for EntryLevel, Jennifer has one goal in mind: to grow the customer base and the brand. For many businesses, a newsletter can be a great way to grow your subscriber base and create deeper relationships with your audience.

As EntryLevel is an online course business in the tech industry, Jennifer’s main content strategy with the newsletter is to showcase EntryLevel’s thought leadership by offering advice on how people can advance their careers in tech.

Jennifer shared, “The newsletter is our weekly tips for breaking into a tech career for everyone who signed up for one of our courses. EntryLevel has been going since 2020, but the newsletter itself started in July 2022. It hasn't even been a year yet.”

One of the best ways to quickly grow a newsletter audience is to leverage a pre-existing social media presence. In EntryLevel’s case, they had a LinkedIn following, so Jennifer tapped into it to boost initial subscriber growth.

She shared, “We ran a giveaway for our EntryLevel audience, where we gave away a free course if people tagged everyone in the LinkedIn comments and got everyone to subscribe. We got a ton of subscribers that way. Everybody who signs up for one of our courses on our websites gets auto-subscribed to our newsletter as well.”

If you offer online courses (or any type of membership), automatically subscribing new members to your newsletter is a great way to build your email list fast. Just be sure that the content actually resonates with these users and it’s part of your terms.

While many people are getting the newsletter as a byproduct of the course they signed up for, not all subscribers are there because of the courses. They’re there for the newsletter content.

Jennifer shared, “As soon as they give us their email and sign up, we have a whole marketing funnel for them. After that, they just get the weekly career tips. It's very interesting because we have people who are huge fans of us because of our newsletter, but they've never bought a course with us before. They're always promoting our courses to their friends because they're like, ‘These people know what they're doing because of the thought leadership in the newsletter.’ But they, themselves, have never paid us or anything.”

What Jennifer has tapped into is a crucial benefit to running a newsletter: targeting a specific audience with great content will almost always result in organic growth. When your content is good enough, regardless of platform, people will share it.

Another way Jennifer was able to grow her list is thanks to beehiiv’s growth features. One she’s taken advantage of recently is beehiiv’s Recommendations.

She shared, “Right now we have just over 62,000 subscribers. Most of it came from people who signed up for EntryLevel. But, we did beehiiv Recommendations and got a few hundred from other newsletters that recommended us. I think 500 to 1,000 are just from recommendations alone.”

Split Content Strategy: Courses & Common Questions

Every successful newsletter starts with a content plan. Here’s how Jennifer strategizes her content into two primary groups.

“I like to split it up. First, there are some trends. For example, AI is a big thing right now. Sometimes I write about that, but mainly if there's something to promote in the business.

For example, when EntryLevel was hiring, Jennifer wrote about her experience working at EntryLevel and tech startups. 

Another way Jennifer approaches content is by listening to what readers are saying.

She shared, “If we don't have a lot to promote at the moment, we have common questions from students that we get all the time. Sometimes people reply to our newsletters and send them in, but most of the time it's people from our support team saying, ‘Hey, this is something that students are wondering a lot.’”

More often than not, when Jennifer writes about common questions subscribers ask through the newsletter and EntryLevel events, the response is positive.

“I'll be answering those common questions. And also, I hear students' inquiries through our events, and I think, ‘Hey, this is something I could write about in the newsletter.’ Whenever I take students' questions like that, I always get a lot of replies saying, ‘Oh my gosh, this helps me so much. This clarified my career path. Thank you so much.’”

Jennifer shared how implementing newsletter content that’s focused on value first is critical to successfully building authority in the space.

“It really builds trust. We're trying to provide free value. I know not everybody can't afford some of our courses, even though we give them a refund if they complete it. Some people can't afford that initial deposit. So we’re just trying to provide help where we can. There's a lot of potential here. People really trust us after reading our content.”

Using Facebook Ads to Grow the Newsletter

Another way Jennifer has leaned into a rapid growth strategy for Level Up is by acquiring new subscribers with Facebook Ads. In fact, Sshe shared that how it’s their primary source of new subscribers.

“Our main channel for acquisition is Facebook ads. It’s basically our performance marketing. We're testing some user-generated content, mostly for Facebook ads and search engine marketing.”

She shared how Facebook ads bring in the majority of new subscribers - mainly, as a by-product of EntryLevel’s course sign-ups - but she’s taking a diversified approach to acquisition.

“We're just starting SEO a little bit, but I didn't do any keyword research or anything for our newsletter. Our newsletter content is mostly questions from students rather than keyword-optimized articles.”

She also shared how EntryLevel quizzes have also impacted growth since they’re so shareable online among friend groups.

“I would say the top channels that people find out about EntryLevel is through Facebook ads and word of mouth. A lot of people recommend our quiz to their friends.”

Newsletter Revenue: Dabbling in Sponsorships

One of the most popular ways to monetize your newsletter is with sponsorships. This is where a brand will pay you a set rate to highlight them within your newsletter content.

Jennifer shared, “Every week, I put sponsors in the newsletter. If we don't have sponsors, I would just highlight EntryLevel in there with a little coupon code where people can get 10% off our courses, and we made some money through that coupon code.”

One way Jennifer has implemented sponsorships is with beehiiv’s Ad Network. It’s an integrated marketplace with thousands of advertisers you can partner with to show sponsored ads in your newsletter. It’s one of the easiest ways to monetize your newsletter with ads so you can earn automatically.

She shared, “beehiiv was really helpful and sent us some sponsors. We did Leader’s Lens and some others, like Morning Brew, and we made some money through that. Every time we do a sponsor, I try to make the content of the newsletter relevant to the sponsor or whoever I'm partnering with. Now, I'm trying to grow and get more sponsors, partnerships, and collaborations. It would be interesting to see if we make more money from the newsletter than from our actual courses.”

Getting Scientific: Testing & Optimizing the Newsletter

Every good newsletter starts with a plan: find the right audience, build great content, and stay consistent. But, one way a newsletter can go from good to great is through optimization. One of the best places to start with newsletter optimization is your open rates.

Jennifer shared, “I've done a lot of experimentation with the newsletter. Because we wanted to get the open rates up, I looked at all of the data from all of our previous email campaigns. I discovered using emojis in the start got higher open rates, especially if it was a red or yellow emoji. Whereas a laptop emoji blends in for users who have dark mode because the laptop is dark.”

Jennifer also shared how testing certain phrases allowed her to improve open rates as well.

“For newsletter topics, anything that says “break into tech” always does really well. Even if I send a bunch of emails that already say “break into tech,” and it's content they should already know, it always gets lots of opens.”

Did you know there’s a best time to send an email newsletter? Jennifer was able to increase opens by simply changing when she’d hit send.

“We used to send our newsletter on Fridays. But, I feel on Friday, people are just checked out and then they don't want to check their emails. I started sending on Tuesdays and that actually got us more open rates.”

For Jennifer, testing and experimenting with different content came naturally at EntryLevel, since they’re focused on teaching about data analysis and growth experiments.

“At EntryLevel, we teach growth marketing and growth experiments. Then we teach data analysis. That's how I learned how to analyze all the data in a spreadsheet. There’s an experiments board on Notion, and I made a page for Level Up’s newsletter experiments. There's the timeline, how long it's going to run, whether it’s statistically significant, what the goal is, and whether it was a failure or a success. All of our experiments go through this template, which is in our growth marketing course. In our course, people have to run an experiment as part of their final projects.”

Leveraging the Newsletter to Maximize Community Engagement

Many people think a newsletter is a one-way channel to speak to an audience. But, the best newsletters know that a newsletter is a two-way street. By encouraging your audience to reply to your newsletter, you can build a tight-knit community.

Jennifer shared, “I like seeing people's replies and comments because they'll always reply and say, ‘Jennifer, this changed my life. Thank you very much for writing this.’ It’s really sweet. Some of them take screenshots of the newsletter content and post it on social media and they're like, ‘Everybody needs to read this.’”

Newsletter replies and comments on your newsletter’s web version can help you interact with your audience by facilitating a two-way interaction. This can be motivating, but, beyond the good feelings you’ll get from positive feedback, there’s also a strategy play here. By encouraging your community to engage with your newsletter, you’ll become more attractive to advertisers.

Jennifer shared, “This is really helpful. There are two metrics that I like to see. The first one is those qualitative comments and people replying. The second one is open rates, just because I think that's what's going to be better for monetization.”

She shared how it’s important to balance the way you structure and design your newsletter for both your audience and advertisers.

Jennifer shared, “I don't think click rates are as important for me because I don't like linking out to things super often unless it's a specific article like, ‘These are the job sites that you could go to to find remote jobs.’ I feel like people don't want to leave their inboxes. It doesn't make for a good experience if you have to open all these different links, especially if you’re on your phone and you have ten different links to open. You always have to go back to the inbox. That’s why the sponsor is one of the only links in the newsletter - it helps the sponsor stand out.”

While Jennifer wants to be careful to structure the newsletters primarily for her audience, she did speak about the importance of structuring a newsletter differently when you start partnering with sponsors.

“We did run some sponsors in the past where we got a high number of clicks, but that's only because I customize each newsletter to be relevant to whatever the sponsor was.”

The same goes if you start sponsoring other newsletters.

Jennifer shared, “When Leaders Lens sponsored us, I made the article all about leadership and made it super compelling for people to want to click on it so it’s one link that is relevant.”

She continued, “I would say open rates and the qualitative feedback is most important because it's very interesting reading the feedback. I like posting hot takes and my opinions on unpaid internships. People's responses to that and everyone's different perspectives were very interesting to read.”

Crafting the Pitch to Sponsors

While crafting high-quality content is a major part of building a revenue-generating newsletter, the other side of the coin is knowing how to monetize. Monetization is a skill you’ll need to develop in order to see your newsletter turn into a real business. Understanding how to pitch sponsors will go a long way in the newsletter game, and Jennifer shared some tips on how she speaks to them to get them interested in working together.

She shared, “I mainly talk about our audience's interests. All of our subscribers are interested in tech and breaking into tech. A lot of them in the past have probably spent some money on learning and courses. We wouldn't promote a direct competitor, but we would promote something like a job search platform, or some career coaching, or maybe another newsletter that teaches people skills.”

When it comes to closing a sponsor on your newsletter, it all comes down to aligning your audience to a brand with a similar audience. The better they mesh, the more likely you’ll be to sign a deal.

“We have a sponsored article coming out with the Refind app. That's an app where you just learn new things through articles. And our audience loves learning. They love learning new skills and I know that it's a great fit for them.”

Jennifer shared how it’s not just about the audience's interests, though. Sponsors want to see real numbers—metrics like your subscriber count, open rates, and buying history.

“I pitch their interests more and say, ‘Hey, there's already proof that they're interested in this. Some have already paid for this, and our open rates are higher than the industry average of 33% for 62,000 subscribers.”

Taking Notes From Other Publications to Optimize the Newsletter

If you want to succeed in any area, you must learn from the best. The same is true for newsletters. Jennifer keeps tabs on a few different newsletters she likes so she can continue improving her own.

She shared, “The only newsletter I stay subscribed to is Ariyh, which is scientific marketing insights. That one's really good. Especially with a psychology background, I find it very interesting. I take inspiration from how they present [their newsletter]. All the information is very clear and easy to find with the headings. I try to do that with my headings as well.”

Jennifer continued, “I like Josh Spector's For the Interested” because it was short. I think once a week—when I read it, I learn something new and that I can apply it to my life. It feels like the vibe where you sit down on a cold winter night, have a cup of coffee or tea, and just read it.”

Jennifer shared that while she has taken a lot of inspiration from some of her favourite newsletters, she doesn’t follow the same format since the Level Up newsletter serves a different audience.

“I like reading those newsletters, but I feel our audience wouldn't. I think I'm pretty close to the users, and I talk to them for user interviews, and I know what they would like to read. When I write, there's a very specific person or audience segment that I keep in mind. For example, I prefer shorter newsletters. If it's a few sentences, that's best for me. But, I know that's not what our audience would want. Our newsletters are always a bit longer: 600 to 1,000 words. But, there are a lot of headings. All of the images—I have to add alt text to them, because I know sometimes, with the internet connection in some countries, the images never load for them.”

Listening to Subscriber Feedback for Content Ideas

One of the biggest challenges of running a newsletter is simple: it’s figuring out what to write. Coming up with content ideas is half the battle. One way Jennifer comes up with newsletter topics is simply by asking her subscribers what they want to see.

She shared, “Sometimes I’ll run a poll: ‘What content would you like to see?’ And they'll vote and I'll look at that. But then, I'll match it against what the numbers are actually saying. The highest open rates so far have been anything that says ‘Break Into Tech.’ Some of the LinkedIn and mentorship newsletters did very well, matching what people are saying.”

Jennifer shared how she often wants to write about topics, but she knows it’s more important to write about what her subscribers actually want.

“I wanted to write some newsletters based on productivity and how to learn more effectively. But it wasn't as popular. I stopped doing that and focused more on the career side.”

Throughout her time running the Level Up newsletter, Jennifer has learned that people don’t always say what they want. Sometimes, what they want is slightly different from what they say. So, she’s learning to interpret her audience’s feedback.

She shared, “I think sometimes people say things and they don't actually need it. A lot of people are like, ‘I'm just here to get a job.’ But then I write, ‘This is how you get a job,’ and it doesn't do as well as another article where it's more talking about the mindset.

What a subscriber would want to read, versus what they say they want to read can be very different sometimes. You just have to test it out and look at the data.”

Goals for the Next 3-6 Months

The future is looking hopeful for Jennifer and the Level Up newsletter. With over 60,000 subscribers, she’s already grown her newsletter to a size that takes some creators years to build, if they ever get there. She plans to keep focusing on growth while optimizing her content distribution.

“For future plans, I want to grow more and streamline content distribution. That's my number two goal. Some of the newsletter content is very useful and could be repurposed as reels, social media carousels, and Twitter threads.”

Jennifer shared that she’s already experimented with repurposing Twitter content and has had mixed results.

“I tried [re-posting to Twitter] once. It took a little bit of time. And then we got two likes. Whereas another tweet I posted, ‘Hey, we're almost at 8,000 followers. Please retweet and we can learn together,’—That one got many retweets. And then the thread I put more effort into got two. It’s funny. I think that happens to social media managers all the time. I'm used to it, but I just want to streamline the process a bit more.”

“I have posts scheduled all the way to June. All the drafts are ready. I have to do that since I also do a lot of other stuff for EntryLevel. I will start getting sponsors and partnerships for each of those articles.”

If you’re interested in following along with the Level Up newsletter, you can subscribe here. Or, you can read some recent newsletters like Get a tech job in 6 months or Hot take: stop offering to work for free.

And, if you’re looking to fast-track yourself into a career in tech, you can check out EntryLevel’s courses here.

Thanks for reading!