12 min read

Educator Stories: Converting from solo educator to organization
Learn how Erika Berry-Cherry grew her online teaching business by expanding her reach as an organization on Outschool.

Have you ever considered switching from being an individual online educator to creating an organization? Maybe you’ve played around with the idea but are struggling to decide whether it would benefit you. 

We talked to Erika Berry-Cherry about how she went from a solo educator to running a thriving organization on Outschool. Keep reading to find out:

  • The nuts and bolts of applying to be an organization
  • How to hire teachers you can trust
  • Marketing and keeping your momentum
  • Business tips for organization administrators
  • Collaborative curriculum design and evaluation

Meet Erika

Erika Berry-Cherry, the founder of Cherry Learning Center, first joined Outschool as a parent in the summer of 2017 when looking for something to keep her daughter busy in the summer. At the time, she was a brick-and-mortar teacher enjoying what Outschool had to offer.

Fast-forward to 2020. In addition to the pandemic, Erika had moved to a new state, had a new baby at home, and was looking for something to keep postpartum depression at bay. Without family nearby or friends in her new hometown, Erika decided to start teaching online at Outschool. 

Luckily, the timing was right, and Erika quickly found success online.

Erika’s journey

Erika wants you to know that if you’re thinking about becoming an organization, you should go ahead and do it. Before you start the process, consider your reasons for building an organization.

“I’ve always had a passion to have a school. I just didn’t know what that would look like. I’ve always manifested, okay, I want to have my own school. I want to be able to educate people. That [idea] stemmed all the way back from when I was younger.”

As a child, she was diagnosed with dyslexia, which inspired her to get into education and create an inclusive environment where learners of all learning abilities could thrive.

“I had so many accommodations and honestly, growing up in the South, I just did not have the teachers that were willing to accommodate me. When I became older, I always vowed to be that type of educator that’s gonna accommodate learners that needed [what?]. I want to be a teacher and not just a teacher. I want to own my own institution, my own school.

Once Erika succeeded as a solo educator on Outschool, the dream of owning her own school seemed much more achievable. These days, Erika is making three times as much as she did as a solo teacher, and has three times the enrollments as well.

How you can get started

As online educators, there are many benefits to teaching virtually. One of those is the flexibility that comes with creating and customizing a curriculum, teaching about topics you’re passionate about, and even deciding when you want to offer classes. 

The one thing that an individual doesn’t have is endless time. Many educators with thriving solo businesses on Outschool arrive at the same point eventually: How can I keep growing, when I’m doing every job behind the scenes and on-screen?

As a solo educator, there are only so many hours a day to offer classes that work with your schedule. So how do you reach more learners and teach more classes when there is only one of you to go around?

Start an organization, of course! Organizations on Outschool are business entities (sole proprietorships, LLCs, etc.) that consist of a minimum of 2 teachers. Organization administrators (like Erika) may continue to teach on the platform, and also list classes hosted by teachers they hire and pay to teach for their org.

Realizing this, Erika evaluated what was working and what she could improve by expanding her business and resources

First, she realized that working around her family’s schedule and having a newborn at home meant that there was only a limited window of opportunity for her to offer classes. It was then that she knew that it was time to get serious.


Strategies to create an organization

These days, Erika runs a highly successful organization that still includes some of the original students she taught before the transition. If you’re thinking about converting to an organization, here are a couple of strategies that Erika has used.

If you’re currently an Outschool teacher, we welcome you to apply to become an organization, as long as you’re looking to enable multiple teachers to teach the same curriculum on Outschool, under a cohesive organization brand.

If you’d like to convert your existing Outschool teacher account to an organization account, please complete the application while logged in. Once your account is converted, it can no longer be used as an individual teacher account. Your reviews and classes will transfer to the organization. You must make sure you have an individual teaching account within your organization and you must teach your classes through that account; you may never teach through the org admin page.

If you want to retain your existing teacher account and create a separate organization account, log out of your Outschool account, then create a new account to apply as an organization. You’ll need to use a separate email address from your teaching account.

Once you’re ready you can apply to become an organization online. During this process you will want to ensure that you’ve checked your educator’s expertise, can provide detailed information about your organization’s goals, and put together a compelling story about what your organization will teach on Outschool.

Hire someone you know and trust 

Erika’s first hire was her twin sister. Doing so turned out to be a smart move for her as she could deal with the ups and downs with someone who she knew would stand by her side during the learning process. 

After a couple of months of working out the kinks of running an organization, Erika and her sister began looking for educators in online ESL communities. Again, the timing worked out beautifully. Due to some shifts in the global online ESL education market, many ESL specialists were looking for new opportunities in 2021 at the same time Erika was hiring.

Erika’s advice? Hire someone you know and trust before expanding your organization. Taking that extra time to learn the ropes with someone who is there to support you can make all the difference.

Treat it like a family business

Although Erika created the first curriculum used in her organization, she now seeks the opinions and ideas of the educators she has hired to develop new classes and lessons.

As the owner, Erika takes the time to train each of her hired educators before putting them into a classroom. For a week and a half, her new hires train for six hours a day on how to use Zoom, understand the Outschool platform, Nearpod, and many other things so that they can feel comfortable and prepared on their first day live.

“Maybe that personal connection matters in the beginning. It definitely matters [for us] because…once we did hire a teacher, we realized that you just can’t throw them into a class. You have to really build that relationship with them, that classroom relationship, that business relationship, and a personal relationship. That really means something to us.”

Today, Erika and her sister create most of the curriculum and work on the business side of things. And her educators? They’re busy teaching and implementing their ideas in the online classroom.

Use increased resources to customize lessons

“I absolutely love being able to [focus on individual learners] because, in the [brick-and-mortar] classroom, I wasn’t able to do that because you were on this very strict guideline. And also we couldn’t cater just to one learner. You would have 25 learners in the classroom including three special needs learners, and then they’re just lost because we didn’t have the funding to help them or for me to just spend that one-on-one time with them.”

Erika credits a good deal of her success to the special attention that she has been able to give her learners since the beginning of her online teaching career. She didn’t want to lose that when she handed the reins to other educators. 

Now, she runs roughly six to eight classes per hour designed for elementary-age learners, something she could not have done on her own.

These days, she checks in regularly with her team, and they celebrate the wins together.

Make your curriculum collaborative

Having multiple educators on board helps you, as a business owner, get a new perspective on what’s happening in the online classroom. Since you can’t be in all the classes all the time, your educators are the eyes and ears to what families are looking for.

So what did Erika do? She made it a team effort.

“We had the aha moment. It was like, how about we take a break from teaching for two weeks and we all come together and we’ll build curriculum together.”

Taking the time to work as a team and focus on how to teach multiple learning levels and learning types has paid off, and the results are in the reviews. According to Erika, the families are loving the updates to the curriculum. Erika’s decision to let everyone contribute also empowers educators to contribute their own ideas. 

Since collaborating, Cherry Learning Center now offers more hands-on, interactive activities in their classes. That is a huge win for learners as well!


Don’t overcomplicate things

Understandably, when thinking about converting to an organization, one of the things that you might be concerned about is the business responsibilities of owning and running an organization. 

Thankfully, there are plenty of software and AI tools available to help you get started.

But what if you are ready to hit the ground running, or can’t afford the additional costs of business management software?

According to Erika, there is a simple, free way to do it all.

Cherry Learning Center runs on Google. Erika and her team share schedules, notes, curriculum, and more through Google Docs and Google Sheets. They even use Google To-do List and Dropbox. The best part? The information is shareable between the team so that when a change or update occurs, everyone knows. 

Include marketing from the beginning

While Erika’s learners did follow her from being a solo educator to offering classes as an org, she knew that marketing was an important part of getting new customers

During the summer, when families are gearing up for back-to-school, Erika starts posting Facebook ads to gain attention and draw learners to her organization’s classes. She focuses on using relevant keywords and posting to homeschool groups in the United States. 

Over time, these learners have shared their experiences with others and spread the word far and wide. Using promotions like “Give $20, Get $20” have been another effective way for families to share their favorite classes. The referral link allows families to try out one of Cherry Learning Center’s classes for a discounted rate.

Keep in mind that you can always reach out locally as well. 

“Within the last year, we’ve been doing partnerships with our local schools and local YMCA Boys and Girls Club.” 

Offering discounted rates or coupons to local schools, afterschool programs, or youth programs can help you find families and learners looking for additional support who may not know what is available online.

Between learners reenrolling for new classes, Facebook ads, and word of mouth, Erika has been able to keep a consistent amount of learners in her classes. 

Soak in the moment

When asked if there was any one thing that Erika would change about becoming an org, her answer was simple: 

“Just soak in the moment, you know, soak in the moment. Be proud that you finally became an organization instead of hitting the ground and running.”

When you switch from being a solo educator to running an organization, there is a lot to do. But Erika says the real magic is paying attention to the present and realizing it’s okay to rest.

One final piece of advice

Of course, in addition to all the helpful strategies Erika shared, she has some advice for anyone who wants to start an organization. 

“For someone that might be sitting on the fence, I would say just do it. If you had the thought to do it, that means it’s meant for you because the thought would have not come into your head or your brain if that wasn’t something the universe wanted you to do.

You can be successful in doing it if you play your cards right. If you do everything that you know that you’re supposed to be doing, like parent communication, and promoting yourself, you know exactly what you have to do to be successful. Yeah. No one else can tell you what you need to do.

No one can take that away from you, especially if you thought about being an org, you should probably apply to be an organization.”

For more information on getting your organization started, be sure to read the following articles:

Organizations on Outschool

Outschool’s Policies for Organizations

Organizations on Outschool Facebook Group

Ready to apply? Start your journey as an organization by applying today.

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