Caitlin Pyle Success Story

Caitlin Pyle Breaks Free with WP Courseware

Today, we had the opportunity to chat with Caitlin Pyle and hear about her incredible WP Courseware success story.

Proofread Anywhere

Have you ever dreamed of being able to work anywhere, anytime? Maybe sitting on the beaches or balconies of some far flung country with your laptop while earning a full-time income with nothing more than an internet connection?

Technology provides time and location independence for a lot of employees, allowing them to work when and where they want. But it has also created amazing opportunities for aspiring entrepreneurs.

Caitlin Pyle is a former marketing executive who found her life slipping away while buried in the rat race spending her hours working for someone else. She was burned out, unhappy, and looking for a change.

The company Caitlin originally stepped into after college was an agency for court reporters. Although she initially began her work with the agency answering phones, her drive and motivation pushed her up the ladder until she was in charge of the marketing department and cold-calling new clients.

As most of you know, court reporters are used by attorneys and courts to produce a verbatim transcript of a legal proceeding. They have to work quickly and the shorthand process of producing these transcripts can result in many grammatical and spelling errors. Therefore, court reporters will often hire a third-party proofreader to correct any mistakes. The proofreaders typically bill the court reporters on a per-page basis and as you can imagine, the work can be done anywhere and, in most cases, any time. In fact, Caitlin’s recommended workflow for proofreading transcripts involves an iPad and a $10 app.

Be sure to checkout Caitlin’s video interview

Caitlin’s Interview

Fly Plugins: Caitlin, how did you come up with the idea for creating a course in this niche?

Caitlin Pyle: People actually ask me how I got into what I do ALL the time! How can I get into something like that? It’s funny how often people ask me. And before I realized how unique it really was, I used to spend hours writing super long e-mails explaining how I do what I do, and I used to personally sit with people and train them. One of two things would happen. The first was nothing. I’d spend tons of time mentoring these people and they decided not to do anything with it, effectively wasting my time. Some folks never even responded to my e-mails! The second thing that would happen was people would actually start making money based on my advice. So they essentially got a new career because of me.

My husband, Ben, recognized both my repeated frustration when people wasted my time, and the fact that when people did not waste my time, they benefited from what I had to offer greatly. After quite a bit of prodding from him to start a blog/write an eBook, I did both of those things in November 2014. In January 2015, he told me about Udemy, where it’s possible to build and host an online course. I was at first quite intrigued but also doubtful I could make such a platform work for me — they require 60% of the course content to be videos, and the type of work I do is largely reading so it’d be really hard to make a course based on reading video-based. I started to, anyway, unaware of any other possibility, until one day I saw WP Courseware mentioned in the Udemy Studio Facebook group as a way people host courses.

FP: And why WP Courseware?

CP: I looked into it, saw how reasonable and flexible the plugin was, and purchased it immediately! I’ve since seen other similar LMS options that don’t even offer as much as WP Courseware, yet cost so much more, plus you have to pay MONTHLY for it, not just one time.

FP: Any plans for marketing and growing your student base?

CP: Yes — I have an affiliate program for past students which allows them to earn commission on referrals to the course. We do some Facebook marketing and I’ve been tinkering with Pinterest here and there. I’ve also been doing podcast interviews and several work-at-home blog interviews — anything to get the word out about the course. It’s truly unlike anything else on the web and it’s been so cool to see my students complete the program and succeed!

Caitlin’s Course

Caitlin spent several months creating content for what would become the most comprehensive course online for breaking into the business of proofreading. She then chose WP Courseware to manage and organize her course content into an easy to navigate, step-by-step system for helping others change their lives through location-independent work.

The result became and was officially launched in November of 2014. She then organized all of the content into one main course, titled Transcript Proofreading: Theory and Practice, which went live in February of 2015. Within 24 hours of launching the course, Caitlin had earned almost $1,900.00 in course subscriptions with plans for further marketing and growth.


Caitlin Pyle contacted us again 18 months after the launch of her Proofread Anywhere course. She had grossed an unbelievable $1 million dollars in course sales during that time!

Caitlin's main course simply uses the standard WP Courseware course outline shortcode, as well as a sidebar widget for accessing units from within the course.
Caitlin’s main course simply uses the standard WP Courseware course outline shortcode, as well as a sidebar widget for accessing units from within the course.

The main course consists of 41 units across nine modules. The modules contain everything Caitlin’s students need to get started in professional proofreading, including grammatical coaching, how to mark up transcripts, recommended workflows, practice transcripts, how to find clients, and tips for accounting, billing, and taxes.

Most of the units utilize at least some video for the lesson and Caitlin is currently also using S3 Media Maestro to deliver her S3-stored media.

Course units include text lessons, video, and downloadable practice worksheets.
Course units include text lessons, video, and downloadable practice worksheets.

For memberships and payment processing, Caitlin is using Paid Memberships Pro as well as the free WP Courseware + Paid Memberships Pro integration plugin. This plugin allows her to associate her main WP Courseware course with a membership level and automatically assign course access once the student has paid.

The “Proofreading” is in the Pudding

One of the things we found very unique about Caitlin’s site and course is that she’s not just teaching a set of personal skills which may or may not end up being worth the price of admission. She’s offering an actionable guide to creating a real income stream, as many of our WP Courseware customers do. It’s a system…if you put in the time and effort, it works.

And one of the approaches she’s taken to validating her course content is showcasing her student success stories. Just as we’re doing with this case study, Caitlin writes on her blog about real students who have changed their lives through her content. This can be a very powerful approach to marketing for many of our users.

So What to Do with All of This Newly Discovered Freedom?

In July of this year, Caitlin and her husband will be setting off on a year-long trip to South America, where she will be running her business remotely.

Sounds nice, right?

We’ve been looking forward to sharing Caitlin’s story with you and hope you found it inspiring. We certainly have. You can reach out to her or keep up with her journey at


  1. Paul from LSMGuide on March 4, 2015 at 11:31 am

    Great article! Cool to see how Caitlin is using the system… Her site is great too… a lot of best practices to draw from.

    Thank you for sharing… Hope to bump into Caitlin while I’m on holiday and WP Courseware is doing the work while I’m away!

    • Nate Johnson on March 4, 2015 at 11:47 am

      Thanks, Paul!

  2. Karen on March 4, 2015 at 1:51 pm

    Thanks for doing this case study! This is GREAT information, especially to see how someone actually implemented the steps, and what their thought process was! Hope to see more of these case studies going forward this year. 🙂

    When you decide to “make the leap” and offer training online, there is SO much more to it than just uploading & formatting the actual course content(like marketing, payments, course structure, etc.). Addressing all these topics is of huge benefit for those of us in the “planning” stages! 🙂


    • Nate Johnson on March 4, 2015 at 1:58 pm

      Thanks, Karen! We’re glad to hear that you found this case study helpful. You’re right…there is much more to the process than just repurposing your past content. We do plan to work on more of these in the coming weeks and have already started on another upcoming case study which we think you’ll enjoy.

    • Caitlin Pyle on March 4, 2015 at 2:35 pm

      It was quite a bit of work figuring out the other various plug-ins, like Paid Memberships — I had to figure out how to personalize the plug-in for my own site… for example on PMPro, everything was pre-made for “Membership”, and I had to go through and change it to be for “Enrollment”. Then figuring out how my students were going to log in, navigate through the course, etc…. just making it user friendly! I spent many hours figuring it all out!! There’s also SSL certificates, setting up the payment gateways… so much stuff! But once it’s done, it’s done 🙂

  3. steven murray on March 4, 2015 at 2:47 pm

    Hi Guys

    Looks like a great product, so we’ve purchased it along with S3 media maestro, PM Pro and Mailchimp!!

    We’re developing a whole new website to really try and capitalise on the e-learning and m-learning strategies for the range of training courses we currently only offer in a class type environment.

    So my question is… “Is there a group (or course) of tutorials on offer anywhere??”

    I’m not looking to become an expert (yet!) and i’m fine with outsourcing this stuff; but it would be great if I could get a handle on using WP Courseware, your S3 media maestro and maybe Paid Memberships pro & Mailchimp!!

    I know its probably asking a lot here, but any guidance would be a huge help.

    To a successful future!!

    Steve Murray

    • Ben Arellano on March 5, 2015 at 1:55 pm

      Hi Steven,
      We have tons of tutorial video’s on our YouTube Channel. We even have a tutorial on how to integrate WP Courseware with PMPro.

  4. Marshall on March 5, 2015 at 1:35 pm

    Good article and case study. Thanks for sharing. I will take a look at her site and see how to set mine up.

  5. Dwane on March 7, 2015 at 3:36 pm

    Guys, I am interested. Can someone explain to me the different site licenses? Do I have to purchase licenses for just my site, or for each of my students as well?

    • Ben Arellano on March 10, 2015 at 1:05 pm

      Hi Dwane,
      Basically it’s one license per WordPress installation. So if you have 7 WordPress sites, you’d probably want to purchase the 10 site license. If you have 20 sites, then 25 site license.

  6. Kat Sturtz on May 12, 2018 at 7:58 am

    I’d love to know what affiliate plugin or system Caitlin and others are using.

    • Ben Arellano on June 11, 2018 at 4:10 pm

      I’m not certain what Caitlin is using, however, we use Affiliate WP and it works great! In the past we’ve used Affiliate Royale which is also a great alternative.

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