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Words at work

– 27 min read

Helping everyone become a better writer and content strategist: interview with Ryan Farrell

Ashley Coolman

Ashley Coolman

Last week, I had a fun conversation with Ryan Farrell, a content strategist at GoodRx. You may know him as the brains behind the Daily UX Writing Challenge and an upcoming course on SEO for the UX Writers Collective. As if that wasn’t enough, he’s also helping build a Los Angeles UX Writers Meetup Group with Kathryn Strauss (who helps manage the San Francisco UX Writers Meetup) and balancing family time.

We spent our time talking about his work with content strategy and UX writing, how he accidentally became a career coach for a huge community of writers, and his advice for people looking to improve their content strategy, UX, and copywriting skills.

Because the interview is quite long, here’s a quick table of contents to help you skip around the conversation:

  1. Introduction to Ryan Farrell, content strategist at GoodRx
  2. The content team at GoodRx
  3. Why GoodRx built a centralized content team
  4. How Ryan got into content strategy
  5. Being flexible as a content strategist
  6. Making content friends and improving in your career
  7. Content mistakes to learn from
  8. What makes good content
  9. Building the Daily UX Writing Challenge
  10. How people participate in the Daily UX Writing Challenge
  11. List of writing skills people practice during the challenge
  12. Daily UX Writing Challenge feedback
  13. Building a SEO and content course for the UX Writers Collective
  14. What people will learn in the SEO and content course
  15. Top three tips for people hoping to break into content strategy
  16. Content strategy and writing resources

Hope you enjoy learning from Ryan as much as I did!

Content strategy Q&A with Ryan Farrell

1. Can you start by introducing yourself and your current work in content strategy?

I currently work at GoodRx. Our core product is basically a search engine for underinsured or uninsured people to save money on prescriptions. So, essentially, it’s an aggregator that shows you the cheapest price for your drug if you don’t have the option of having an insurance company pay for that drug for you. Which, unfortunately, a lot of people in the U.S. find themselves in that position.

There’s a number of different business verticals in the organization that content strategy touches. I’m currently working with the research team on the long-form top of funnel content. So, building out the blog, evaluating new CMS technology, designing the CMS information architecture, and outlining the larger content strategy of how a repository of content relating to health conditions (e.g. diabetes, allergies, stuff like that) is going to fit into a cohesive education hub.

In the past I’ve been involved in projects as varied as microcopy, navigation projects, onboarding, registration. You name it, I have to do it.

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2. How many people are in your organization? How many work on content? Are you all in different teams or together?

GoodRx is probably hovering around 200 people right now. When I joined just over a year ago it was just above 100 people, so we’re growing at a fairly rapid clip.

People devoted to content, I want to say there are around 16. We’re all primarily on the research team, which includes medical editors and data scientists who are responsible for consumer-facing studies around drug pricing and related topics. With this team structure, we have the people responsible for generating the consumer-facing “head” of the brand, product, and user experience in one department.

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3. Why did GoodRx put most content people in the research team?

If you follow our model, the single content department ends up having the most subject matter expertise when it comes to your topics. Which means you’ll write better content.

Organizations that say, “Okay, we’re going to write about something. We’re going to generate a piece of content that has a keyword density of X and meets a need, and then we’ll get traffic,” don’t have a content strategy. They have bad SEO.

I’ve been in organizations with writers who have a chameleon-like ability to generate content that sounds legitimate even though they’re not experts in that topic. But there’s always just something missing. In good articles, there’s always an X-factor, that spark of know-how that exists when an article has been written by somebody that has done this and cares about this. Which is hard to quantify, obviously.

Instead, organizations should say: “Okay, we’re going to run a fintech blog. We need to get people with finance experience to write that content. If they’re remote freelancers, that’s great. But we’d really like to have one or two people in-house running shop.” I think these orgs are better set up for success. The companies that put a high premium on know-how and subject matter expertise — and then put those people in charge of generating the words that the product says — do the best.

The companies that put a high premium on know-how and subject matter expertise do the best with content.Click To Tweet

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4. We skipped this, so let’s back up to before your time with GoodRx. Can you talk about your background and how you got started in content strategy?

I was a musician for all of my 20s, which is a strange start for a content career. But I’d always been a fairly decent writer, though very untrained when I was younger. I actually managed to get through college not fully understanding the basics of good grammar. (I’ve since retaught myself.) But I got out of music when I decided that I had to get a steady job.

Lo and behold, there was this bright new world of internet and online marketing that was like the Wild West when it came to barriers to entry. I had a friend who started an online marketing agency and they were looking for an SEO content strategist. So he asked, “Hey, do you know anything about SEO?” And I said, yeah, absolutely! …I had heard of it. But again, it was the Wild West, and I got the job.

From there, I just worked really hard to make things happen. I worked my way up in the organization and, before long, found myself in charge of the entire content and design department. It was fantastic and a huge step for me. To this day, it’s a very proud accomplishment.

Then I decided that I wanted to step back from management. I want to keep making things and advancing in a path of product building, not necessarily people management. I joined TrueCar as a UX writer for three years, which was a great learning experience and a lot of fun. During that time I was the only content person in an organization of 300 engineers, which is a lot different than the situation where I find myself now.

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5. Do you think your years as a musician helped mold you into a great content strategist?

I think being a musician taught me flexibility, and that’s been very helpful in the content world. You can’t be too rigid about your process… nobody follows it anyway! At the end of the day you have to be flexible. “Alright, cool. Slack me the request. No, I don’t need a ticket. It’s fine. I know how you operate. We’ll make it happen.”

I think being a musician taught me flexibility, and that's been very helpful in the content world. At the end of the day you have to be flexible.Click To Tweet

Yes, there are very, very, very valid arguments for why you should never adhere to my process (or lack thereof). But I’ve found that if you’re the first content strategist to arrive in an organization and you’re dogmatic about processes — getting in everyone’s face about it, having lots of arguments — it becomes very tense. Your teammates are not going to have a good opinion of content people.

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6. Yeah. If you don’t make content friends, you don’t make progress. So how do you make friends and improve in your career?

You have to bend like a reed in the wind for a little while. Once people start to realize how good you are at what you do, then they bend. You start hearing: “Okay, you’re right. I’m totally putting this on your plate in the wrong way. You’ve asked me to follow your process multiple times. Let’s do it.” At that point, you’ve earned some political capital. You can make things happen.

It’s unfortunate that we have to learn to be “the flexible one” as content strategists, but it’s also kind of neat. You get to make your own rules as you go. You get to write your own roles and career. Not a lot of people can say that. Engineers have very strict paths guiding what they can do every day. There’s not a lot of wiggle room when it comes to code commits and code reviews.

You get to make your own rules as you go. You get to write your career. Not a lot of people can say that.Click To Tweet

If you’re the type of person that enjoys a little bit of latitude, a little bit of freedom and flexibility, and interpersonal challenges as much as intellectual challenges, then content strategy is a good field for you.

If you're the type of person that enjoys a little bit of latitude, a little bit of freedom and flexibility, and interpersonal challenges as much as intellectual challenges, then content strategy is a good field for you.Click To Tweet

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7. Do you have any stories or mistakes you look back on and think, “What was I doing?” that others can learn from?

Early on in my career I had a totally undeserved big win with a piece of content. I didn’t do much upfront research to substantiate why this piece was the right piece, but lo and behold it did great. I took credit for the success, of course, but it was a fluke. But everybody thought I was a hero and I thought, “Oh, cool. This is easy. I can do this every time.”

So the next, literally, the next project where I was positioned in a similar situation, I took the same cocky approach of, “No, no, this is my gut feeling. I’m just going to go with this. Let’s just make this thing. This is the way it should be.” I tossed the clients aside, tossed the users aside, even went so far as clashing with my teammates about what we should be making.

Obviously it bombed. It was embarrassing and ridiculous. After that, I did a post mortem to figure out what went wrong. The truth of the matter was that I did not follow any sort of structured design process. With the first project I just got lucky, and I thought that I could just ride luck throughout the course of my entire career. Which was just insane. It was a really humbling moment to realize, oh, maybe I’m not as good at this as I thought I was.

But it taught me the value of process and “just enough” process to get to a repeatable quality that will get you results. Maybe you won’t get an, “Attaboy!” from the CEO, but you will get the job done and you will do consistently good work.

Lesson to learn from me: You need a repeatable approach. Follow the design process. Do the research, make a quick and dirty version of what you want done, test it, refine it. If you do that, you’ll get a good result almost every time.

You need a repeatable approach. Do the research, make a quick and dirty version of what you want done, test it, refine it.Click To Tweet

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8. Now that you’ve worked in content strategy for a while, how do you define “good content”?

I get this one a lot. So, you can identify the metrics you can look at to know if content is working: inbound links, PR hits, small bounce rate, great time on page, ranks very well for a lot of different keywords (if you’re talking about something long-form). But those are all just data points you put together in a chart so that you can say, “Okay, cool. This works. Start making more of this.”

But, to me, a really good piece of content is that article that you can’t help but share. Even if it’s just one person who you think should read this and you send it to them. That’s a really good piece of content.

A really good piece of content is that article that you can't help but share. Even if it’s just one person who you think should read this and you send it to them.Click To Tweet

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9. So, let’s switch gears a little bit. Lately you’ve been working on several projects to help other UX writers and content strategists grow, such as building the Daily UX Writing Challenge. What kickstarted that idea?

It was a personal challenge for myself that turned into something that hopefully people will keep getting a lot of value out of it.

When I started actively interviewing in the UX content world — several years ago now at this point — I was actually taken aback at the lack of information out there about how to prepare for a UX writing interview. There was just nothing.

That stuck with me as a huge gap in our community. There’s always a content challenge when you try to get a new writing role. Sometimes it’s, “We want you to write a long form piece of content on this topic,” and other times it’s, “We want you to respond to these prompts, in this amount of time,” and they’ll get progressively more difficult. For engineers, there are all sorts of websites designed to help them prep for their coding challenges; people pay money for literal software services as they’re going up for engineering jobs at Google and Amazon and other big tech companies. But there wasn’t that research or collateral out there to help people prep for these UX copywriter challenges.

I’m also a hobby coder on the side, and at some point I decided I wanted to challenge myself to build a website from scratch. Not using a CMS, but literally from scratch (which I don’t recommend).

So I took these two things to start my project — the Daily UX Writing Challenge. I had collected and iterated over a bunch of UX content prompts for my own interviews. I decided I could use those to set up a 14-day challenge for people to help them prep for writing challenges. I thought that if 10 people get use out of it, then cool 10 people get use out of it. It was just my time and I enjoyed working on it. If not a single person had signed up, it would have been a rewarding experience all the same. At the very least I will have coded a website myself.

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10. How long did it take to finish the project? What happened next? How do people participate?

I was the designer, developer, and writer of the whole project. It was really a challenge for myself in that I’d never truly done all those roles (though I’d stepped into each from time to time).

Three months into the project, I forced myself to call it done; I had to start showing this to people. I literally had no paid search. No promotional strategy behind it. Not a lot of SEO traffic to speak of. I shared it in a couple of Slack communities and, before I knew it, people were signing up.

Within the first day I started to realize, whoa, I may have something here. I had around 50 signups. That’s an extremely modest number in the grand scheme of things, but when you’re talking about a small community like UX writing and a very tiny website that just launched with no fanfare whatsoever, that’s pretty good engagement.

I quickly started getting emails from people sending in their work. In the beginning, I was trying to give feedback and trying to be as present as possible. As they kept coming in, I realized I couldn’t keep up. They were all really good and I wanted people to get the most out of the experience, but at the same time I had to live my life. I was a new dad.

So now there’s a Daily UX Writing Facebook group for participants. People can post their submissions there and get feedback from the community. So far, that’s worked really well. People aren’t shy about sharing their ideas in different formats, and there are some great writers in that Facebook group. Very, very senior professional content strategists who offer advice to help brand new UXers learn how to become better writers. Technically it’s not true user feedback, but it is excellent feedback from subject matter experts.

These days I moderate the group, watching people interact with and help each other. I see the goodness in humanity there. Plus, it’s fun to see that there are other people out there that are kind of like me.

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11. Do the challenges help people improve specific skills?

I didn’t want to make it feel too much like school, but I did want each challenge to focus on a different way of writing to a user. I tried to introduce different elements of copywriting and content strategy into each challenge. For example:

  • You need to convince the user, you can use this tactic of persuasion.
  • You need to instill a sense of urgency.
  • This is for an onboarding experience.
  • This is a very serious alert message.
  • You need to get the user’s attention with a very limited character count.
  • Here’s the tone you should use for this message.
  • This is an SEO challenge, so here are the basics of SEO.

In my opinion, once you’re good at writing onboarding, registration, forms, and top of the funnel content, you can pretty much do anything. These challenges are all very real things that content strategist encounter every day. The newsletter is designed to simulate those as best they can.

In my opinion, once you're good at writing onboarding, registration, forms, and top of the funnel content, you can pretty much do anything.Click To Tweet

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12. Have you heard any cool success stories? What type of feedback have you gotten from people?

The challenge has been around a year now. Some people do reach out and say things like, “Hey, your challenges started it all. They made me want to do this, and I love it. I just got a job at Apple!” and that’s awesome. But I don’t credit myself. I credit these awesome people who have the drive to engage with this challenge and make this career work for them. It’s been really rewarding to be a small part of someone getting, maybe, the first job they’ve loved. Which could translate into an amazing career.

Before the challenge, I’d never experienced anything like this — influencing and helping people become the best professional version of themselves. I appreciate being part of that; it’s special to me. I imagine this is probably how teachers feel. Well, they probably feel a lot more because they do a lot more work than I do. But, helping people and putting something together that enriches their lives… they do better for it and you do better for it and it’s just great. It’d be cool if the whole world worked that way.

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13. Speaking of teaching, you’re also working on a course for the UX Writers Collective. Can you tell me about it, what spurred that project, and what you’re hoping to teach people?

The UX Writers Collective is an extremely talented group of people. Their wealth of experience in UX writing dates back to the very early days of the internet. I’ve been working as a formal advisor and I have experience in things like SEO and online marketing, so I help them with getting the word out.

For the past eight months, I’ve been working on creating my own course. It’s been a long, long process of writing. The crux is this: there are a lot of SEO courses out there, and now there are a lot of content strategy collateral and resources too, but there aren’t many that discuss both. So that’s the aim of this course — marrying SEO and content strategy.

Unfortunately, a lot of organizations separate SEO from content. Yes, there’s a technical side to SEO, but, at the end of the day, the search engine is crawling strings and sentences and content. It’s literally looking at the words on your website. I’d like to see more organizations realize that, yes, SEO is definitely a technical expertise, but there’s also there’s a professional and subtle nuance to it that’s more akin to copywriting and content strategy than most people think.

Yes, SEO is definitely a technical expertise, but there's also there's a nuance to it that’s more akin to content strategy than most people think.Click To Tweet

Google is a product. It’s an interface. The search engine results page is a product interface that a lot of engineers and designers and product managers put a lot of thought into making perfect. As a writer who knows SEO, you’re in a position to influence the look of that product. You just need to know (A) the basics of SEO and (B) how to write persuasively and flexibly on multiple interfaces. The upshot of it all is that if you know SEO as a copywriter, you can charge a lot more and you can make a lot more money.

So, we’re hoping that we’ll be able to do a lot of good. I don’t have a launch date for it yet. Maybe mid this year. Keep an eye out!

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14. Who’s the intended audience for the course?

I think that it will be very useful for those UX writers who have a lot of product experience and don’t really know anything about SEO. If that’s you, I think you’re really hamstringing yourself. It’s kind of like being a designer and not knowing anything about data visualization. This is an opportunity for UX writers who are strictly product writers to come and learn about content closer to the top of the funnel.

It’s also meant for people who are new to content strategy in general. Those who just want to get started somewhere. This should be a bit more accessible to them because SEO is not as abstract as UX writing can be. Some people don’t intuitively grasp things like onboarding, registration, or A/B testing an experience throughout a logged-in product, but SEO for blogs and consumer-facing content often feels a lot more tangible.

Overall, the course will be for people who think things like, “Oh cool. I’m going to learn how to make my site look right in Google.” Which is such a simple sentence, but also the crux of SEO. It’s going to talk about how you can rank well, influence click-through rates, influence user behavior, and even A/B test SEO (which is not something a lot of people know).

So hopefully something for everybody. It’s going to be a modestly priced course, so a bit more accessible for people who want to do it part-time.

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15. You’re doing so much to teach everyone how to become a better writer. What are your top three tips to help people break into content strategy?

1. Write a lot. Like, every day.

Even if you just sign up for the challenge, even if it’s just ten minutes a day, do that. Start there. Build the muscles to be a better writer, and know that you enjoy it, because you’re going to be doing a lot of it. Yes, content strategy is about a lot more than just writing, but once you get to the point where it’s time to put words on the page, you better know how to do it. Pick up fundamental books on writing to get the tools. Stephen King wrote a book called On Writing: A Memoir of the Craft, which is fantastic.

Yes, content strategy is about a lot more than just writing, but once you get to the point where it's time to put words on the page, you better know how to do it.Click To Tweet

2. Do the reading on UX and usability.

Know what they are and how they play into the whole product experience. UX was envisioned to be a more broad, fundamental view of a company and not necessarily a single experience. So understand how UX plays into the grand scheme of an organization’s success or failure.

A great primer for anybody who wants to read up on usability is Steve Krug’s Don’t Make Me Think. Basically, don’t make users think too hard. Things should be intuitive. They should also be pretty and delightful and easy to use, but there’s a lot more to it. You don’t have to be a UX research expert, but you have to speak the language and understand how it fits into the broader strategy of putting a thing together.

You don't have to be a UX research expert, but you have to speak the language and understand how it fits into the broader strategy of putting a thing together.Click To Tweet

3. Learn at least one, if not all, of the prototyping softwares.

People are somewhat resistant to this, but I always suggest it. Pick up Balsamiq and just try to wireframe out your own experience. Go a step further if you want and set up a Figma account to try some high-fidelity versions. Learn these tools and learn the design process of how a component comes together on the design side. If you want to take it a step further, go into the code editor in Figma and look there to start learning about code a little bit.

The reason I really suggest content strategists do this is because the job is so dependent on empathy. Empathy for the user, but also empathy for the people who we work with. The designers, the developers. You want to know what their job is so you can better enable them via your job to make the best thing possible. I’m not suggesting you learn how to code, I’m just suggesting you try it and realize how hard it is.

The reason I suggest content strategists learn about design and engineering is because the job is so dependent on empathy — for the user and the people we work with.Click To Tweet

So, those are the three things to start with. Learning about writing, UX, usability, design, and engineering will help you talk to people as you piece a product together. You’ll build core skills for content strategy and soft skills for working effectively with others. If you’re a competent content strategist who understands UX and has empathy and competence in design and code, you’re in a great spot professionally.

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16. Last question: You just listed a few specific resources for people to check out. Do you have any others you’d suggest?

I actually pieced together some stuff yesterday for a presentation, so I’m gonna cheat and send you the list of links. It’s basically a list of blogs, prototyping, testing, and survey tools. (All the different services that I’ve used to help gather substantial user feedback.)

Other than that, two things I want to mention:

  1. I’m co-hosting a UX writers meetup at Hulu in Los Angeles on January 30. We just want to build a community around here to help UX writers meet, talk in person, find job seekers and hiring managers, maybe find mentors to help you with your career. I’m pretty stoked about it. For me, it’s been more challenging to find other LA-based UX writers than it should be! I’m excited for the new community.
  2. The UX Writers Collective just announced their UX Writing + Content Design Summit coming to San Francisco this August. I’ll be hosting a session at the conference, and the list of other speakers so far is already really exciting. There’s going to be a ton of knowledge in the room. I hope everyone interested in what we’ve been talking about in this interview will join!

Ryan’s list of resources and tools

Wireframing & design tools:

User testing & surveys tools:

Prototyping & version control tools:

Articles & blogs:


This has been great, Ryan. Thanks so much for joining me today to talk about content and UX!

It’s been my pleasure. This was really fun.

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