10 Things I Learned in 10 Years of Selling WordPress Products


his week, I wrap up nearly a decade at iThemes. I didn’t want to let this transition go by without reflecting on what I learned, celebrating some achievements, and expressing gratitude to the awesome team that became a second family to me. You don’t spend 10 years together without having some stories to tell. 

If I’m honest, I never saw myself in marketing or even business. I studied art in college, assuming I would go on to a career in the humanities or education. Once I left college, I’ll admit I floated from one non-profit job to another, not sure where I belonged. But that’s when the special place of iThemes welcomed me, introducing me to the wonderful world of WordPress. 

It’s been said that WordPress is a movement, a philosophy. The open-source initiative means freedom: ideas are shared; collaboration is key; transparency is necessary. Like all idealistic notions, of course, nothing is perfect. But I was drawn to these high ideals of empowerment and free expression; I could get behind these values as the foundation of our business. 

What I quickly learned, though, is that WordPress also represents an entire thriving business ecosystem. Talented teams around the globe work every day to bring innovative tools that build on the foundation of WordPress. The WordPress marketplace faces both some unique and universal business challenges. Ask any developer turned overnight CEO; any former art student turned content marketer. 

I gave myself the challenge of distilling down my experience of selling and marketing WordPress products as a way to look back and also a way to look forward. I believe these lessons will continue to be true long into the future. So, here goes.

1. Marketing … with Heart 💛 

Let’s face it: marketing can get a bad wrap. If there was one thing I realized during my first few months at iThemes, it was the challenge of building a marketing approach that was also a bridge between our customers and the rest of the team. 

What I learned was the importance of what I call marketing with heart. It’s an approach to marketing that is built on a few key values:

  • Be helpful.
  • Be generous.
  • Be sincere, authentic, and honest. 
  • Be clear and concise. 
  • Respect your customers’ time (as well as their inbox and timeline)
  • Earn respect with your team. 
  • Commit to excellence. No shortcuts.
  • Do the right thing. 
  • Make people’s lives awesome

With any marketing campaign, I learned to ask myself:

  • How are we being helpful and generous?
  • What’s confusing about this?
  • What exactly am I asking the customer to do?
  • How can I make this action easier for the customer? 
  • Is there anything I’m being lazy about?
  • How can we surprise and delight anyone who reads or sees this?

Of course, all marketing comes with one primary goal: make more money. But I’m here to say you can make money and hold these priorities at the same time.

2. Sell The Thing You Made For Yourself

Quite simply: The WordPress products that took off were solutions we built for ourselves to solve a specific problem. 

For example: 

  • BackupBuddy was built after we experienced a server crash in 2010. We needed a way to completely back up and restore our own WordPress website, so the idea for BackupBuddy was born. 
  • iThemes Security came on the heels of experiencing a server breach, when the need for a better WordPress security solution became obvious. 
  • iThemes Training courses like SEO Bootcamp and Google Analytics Bootcamp were launched because we needed this type of training internally. 

I can think of other examples outside of iThemes, like Restrict Content Pro. Over the course of that acquisition announcement, I learned that RCP was built out of Pippin Williamson’s need for a membership solution. 

3. Your Customers Likely See Your Product Differently Than You Do

One of the more interesting revelations was realizing customers often see the benefits of a product differently than we did. Often, there was a problem the product solved or another major benefit that we weren’t seeing, so we were missing an opportunity to highlight that benefit within our marketing efforts.

The best and only way to figure this out was to actually talk to customers. Interview them. Conduct meaningful surveys. Find out what you’re not seeing. Don’t guess.

Ultimately, knowing how your customers truly see your product better shapes and informs your marketing messaging, the copy in your sales pages, the emails you send, the ads you run. And it can help you focus your development efforts in a better direction. 

4. Simplicity and Clarity Always Win

Donald Miller says The brand that communicates the simplest is going to win.”

I bought into this idea, fully: Simplicity and clarity are the things that will set you apart from your competitors. And I have example after example to prove why he’s right.

In reality, though, it isn’t easy to be simple or clear. Maybe it’s even more difficult in the tech world, where building a product doesn’t automatically mean you know how to effectively market it.

I have learned that the pursuit of clarity and simplicity requires a few things:
  • Willingness to cut out anything unnecessary
  • No shortcuts
  • Intentionality
  • A lot of WORK

5. The WordPress Marketplace Evolves Quickly. Your Business Should, Too

We all know that WordPress is constantly changing. (Hello, Gutenberg!) This change (well, like all change) is always met in three ways: 

  • Resistance
  • Ambivalence (my personal favorite)
  • Acceptance 

The way WordPress core changes will impact WordPress businesses. There’s always the chance that the features you’ve built into plugins or themes may eventually become part of WordPress core. Or the functionality you’ve built as your product may become obsolete altogether. That’s a scary prospect, of course, bringing a level of uncertainty that isn’t for everyone.

We felt the challenge of WordPress change deeply at iThemes. After all, how do we work day-in, day-out improving our products and still be active in the wider WordPress community? How do you do both?

There’s no easy answer, but I can say for sure that staying involved in the wider WordPress community means keeping a better pulse on how WordPress is changing. 

This means:

  • Going to WordCamps
  • Actually getting to know our customers
  • Being active in WordPress.org support forums
  • Contributing to WordPress core
  • Building an interactive community of our own at iThemes Training
  • Building friendships with other WordPress business owners

While the challenge of change will always exist in a rapidly-changing industry, we learned we had to do what we could to stay relevant and continue to innovate. That often meant change within our organization and the products we offer. It meant pivoting to products that reflect the movement of both the WordPress community and the WordPress business ecosystem. 

6. Customers are Real People, Not Just Revenue Numbers

I remember reading something once about the limits of our comprehension when it comes to large numbers representing actual people. This awareness is also a monumental task when it applies to scaling a business and marketing: Each account represents an actual person with hopes, dreams, disappointments, and frustrations.

It can be difficult to hold the enormity of this continually, and I’ll be the first to admit it’s easy to get lost in charts and projections and forecast goals, losing sight of the faces behind all those numbers. 

At the iThemes office, we had an entire wall devoted to the pictures of customers. Every time I walked down the hall, I seemed to land on a new face. For a while, in the office break room, we had a TV that displayed the gravatar of the latest purchase (you never knew WHAT you were going to see). But these small efforts seemed to help remind us of the people behind the profits. 

7. Embrace Competition and Collaboration 

Not long after I started at iThemes, Cory Miller, our former CEO, hosted a “Friends of iThemes” event that included the owners of several other competing businesses. At the time, since I was new to the culture of WordPress, I found it a bit odd that competitors would meet up to talk through their shared challenges and successes … and just hang out. This was my first introduction to a rebuttal of the idea that just because you have competing products you can’t collaborate. 

One thing I’ve learned about the WordPress community is its generosity. I think this speaks to the fact that WordPress business owners, in general, truly want to help their customers. And of course, have a profitable business. We might as well work together.

8. Consistency is Key

All too often, we abandon endeavors if they’re not an instant success or if we don’t see instant results. But I’ve learned that some things take time. (In fact, I have a poster of this quote in my office to constantly remind me.)

Because business can happen at such a breakneck speed, and goals (especially revenue goals) can come with a ton of pressure and urgency, it’s easy to give up on marketing endeavors that don’t instantly succeed. 

That’s why it’s important to make informed decisions on what marketing initiatives are the most important, and commit to them. Really commit to them, and show your commitment with consistency

If I learned anything at iThemes, it’s that content, SEO and email are the secret sauce to great online marketing, especially for WordPress products. But these things take time. They take time to plan, time to produce, time to see results. And more than anything, they require consistency. 

  • Send an email every week, no matter what. 
  • Publish a blog post every weekday, no matter what. 
  • Keep optimizing your old and new content for SEO. 

Don’t give up. It takes time to see the payoff. 

As Gretchen Ruben says, “What you do every day matters more than what you do every once in a while.”

9. See Failure & Mistakes as Opportunities to Learn & Grow

A “growth mindset” culture requires one key philosophy: Failure and mistakes are an opportunity to learn and grow. 


  • You can’t innovate without failing
  • You can’t learn without making mistakes

I’ll admit it outright: I’m a perfectionist. To the MAX. But it’s been one of the greatest challenges of my personal (and professional) life–putting down the heavy shield of perfectionism. 

It’s no secret that we made a few mistakes and had a few failures at iThemes. Some of these mistakes impacted our customers directly, other times we felt the failure internally. 

But each and every one of those things laid the foundation for us to ask the incredibly important question of “why.” Having those incredibly difficult conversations helped us take the mistakes and failure to learn, grow and do better. 

When it comes to mistakes and failure, own up. Communicate the hard truth, even if it means sending an email to your customers. Don’t sweep these things under the rug. Even if it’s painful at first, your team (and your customers) will ultimately respect you all the more for it. There is no pathway to trust without transparency and honesty. 

10. Personal Development Matters as Much as Business Development 

Ultimately, if I learned anything at iThemes, it was myself. When I started at iThemes back in 2011, I had no idea how much I didn’t actually know myself … or what I wanted. 

Most jobs aren’t exactly the avenue for introspective endeavors, but I was handed several resources that helped me learn about my strengths. 

For one, each team member got a StrengthsFinder assessment. 

I learned my StrengthsFinder strengths (or themes) …. 

Another strengths assessment is the VIA Character Strengths. Here are mine for that one:

Ultimately, knowing your strengths helps you sharpen them. When you know where you excel, you can work in your sweet spots. Knowing your strengths also helps you know when you’re working outside of them. With the knowledge of strengths, you can build a better team, where individual team members have complementary strengths. It also helps you see different perspectives, motivations, and priorities. 

All of these lessons helped me realize that personal development matters as much as business development. Work on yourself. Know yourself.

As Thoreau said, “Know your own bone. Gnaw at it, bury it, unearth it, gnaw it still.” Being a self-aware person helps you correctly frame all your motives, reactions, and decisions. This can’t be compartmentalized from professional life.

Wrapping Up a Decade + The Journey Ahead

More than the work and what we accomplished, I’m grateful for the friendships. We climbed trees, we rafted rivers (and fell out), we explored new cities, and we built some kick-ass WordPress products together. I’m thankful to be working with you every day, awed by your talent, your hard work, and your gif game. 

[Press play and continue reading]

To the iThemes team:

  • I’m grateful to Matt Danner, our General Manager, for seeing the potential in me, for teaching me how to shoot a bow and arrow, and for being a kindred spirit about things like finding personal solitude in the woods and drinking good chai. Also, congrats on the Emmy!
  • To Patti, Painkiller, made of pure gold: YOU are the glue. Your thoughtfulness is unmatched. Your kindness and generosity never left even the smallest detail untouched. I miss our walkabouts and conversations dearly. If I ever find myself barefoot on a beach in Hawaii again, you’ll be my first thought. Never stop exploring!
  • To Chris Jean, Wearer of Many Hats: Pizza Parties Forever! You are the most intelligent human I know. Keep thinking, keep baking, keep the cats happy.
  • Saylor Rain: You make all of us (especially Celine!) so proud. I can’t wait to see all the places you’ll go! (With a mink coat). Where do I buy a pass to the flower farm?!
  • Elise: In the nine years I’ve known you, I’ve always seen one consistent thread: you are made for great things. Thanks for all the cakes and commas
  • Sarah: I stand in awe of your spreadsheet skills. Thank you for always being so consistent and patient. And for doing it all while raising 3 boys!
  • Michael: Learner, Grower, Activator, Woo. You inspire me so much to never stop learning and asking questions. Plus, you like cool tunz!
  • Lewser: I would never have known so much about goats without you. I’ve enjoyed getting to work alongside your greatness. Live free and DIY.
  • AJ: Your caffeine intake is a thing of wonder, along with your webcam resolution. Wishing you all the best!
  • Timothy: What a cool thing it has been to get to see your talent expand. Winner forever of Zoom backgrounds. A Paul Hollywood handshake to you, sir.
  • Rebecca: Oh, Canada! Knit on. And take down the patriarchy.
  • Yobani: So glad we got to work together! Thanks for always being so helpful and for the taco recommendations.
  • Thomas: Thanks for your tireless work in supporting customers. I truly wish you all the good things … and a new Rubix cube.
  • Ronald: Afscheid! Still hoping to one day visit the Netherlands. Thanks for being such a great coworker and for all you’ve done for iThemes. Oh, and for the Stroopwafels.
  • Nathan: You taught me so much about WordPress! Thank you for being such a generous teacher and advocate for iThemes.
  • Curtains: I’m bummed we didn’t get to work together longer, but I’m excited to see where your experience and inquisitive nature takes you!
  • Schmatt: Thank you for always having such a bright, helpful, positive attitude. Plus, you brought us the world’s best no-bake cookies. (Thanks, Kels!)
  • Josh: I was always so impressed by your work ethic and positive attitude. Thanks for bringing your skills to iThemes.
  • Jenny: I’ll never forget your story about 9/11. That one will stay with me forever! Thank you for sharing.
  • Jared: While we didn’t get to work together that much, it was cool to see your hard work on RCP. Now, if I could just get a button to cancel my account at a certain online meal planning service …
  • Daphne: I was so incredibly impressed at how you finished a web development program while being a mom while working a full-time job. You are an inspiration.
  • To all the awesome folks at Liquid Web, including Joe Oesterling, Carrie Wheeler, Terry Trout, Mayra Pena & Misty Combs: Thank you for preserving iThemes and giving us a new home to thrive. It was a pleasure getting to know all of you!
  • Lindsey Miller: I must include you among this list of gratitudes. We’ve had so many amazing conversations I’ll cherish forever. I’m so thankful for your friendship and encouragement all these years.
  • Finally, thanks to Cory Miller, our former CEO, for giving me a place to learn, grow, and kick trash cans. I owe so much to you. 

Lastly, I’d like to give a shout-out to all the people out there who may be more comfortable behind the scenes of a business, content to do the work. Don’t try to fit into a mold. Build your personal brand, or refuse to do it out of principle. Seek out other interests besides business. Read for pleasure, take walks, have a hobby. If you despise social media or find it a waste of time, don’t do it. 

At the end of the day, at the end of a decade, only three things really matter:

  • Progress 
  • Passion
  • People