Interview: Kelly O’Brien, Self-Service Content Manager at Kayako

We interviewed Kelly O’Brien, Self-Service Content Manager at Kayako. We took the liberty of asking her all about self-service and documentation.

How did you get into writing documentation?

I went to school for journalism, with a writing minor thrown in for good measure. About five years ago, I was splitting my time between a half-time university gig and freelancing for a variety of trade magazines, when a Drupal developer friend of mine asked if I ever did any documentation work.

I was usually the biggest nerd on my editorial teams, so I had some experience maintaining Drupal websites. I'd also done a bunch of in-house documentation over the years, just for my own convenience.

So, I started freelancing for a Drupal shop in Portland. I picked up an edtech client shortly after that, and then within 3 months I’d dropped all my magazine work, quit my part-time job, and started freelance tech writing full-time.

What is your current role and what team are you on? How big is your team?

I’ve been working as the self-service content manager at Kayako for a little over a year, embedded as part of the support team. 

Even though I’m our sole tech writer, I’m very lucky because I get to work closely with our support, product and growth teams to build our self-service content, and keep it up-to-date.

What is one thing you think your current docs site does really well?

We put a lot of thought into the information architecture for the Kayako User Guide, and I think that’s been really helpful. 

It’s helped us keep our content more focused and modular, which makes it much easier to navigate, share, and build upon. 

What’s one thing you would like to improve in your current docs?

We’re currently working on adding more multimedia to our self-service content, which I’m really excited about. 

I’m a text-oriented person, but I know a lot of people learn best with screenshots, videos and interactive content. We’re working on incorporating more of all these into our docs. 

What’s your biggest personal challenge in your role?

Prioritization! We just launched a completely new version of Kayako this summer, which was so exciting, but it also meant that we had to build up our docs literally from scratch for the new product. 

There are so many parts that needed adequate coverage, each of which takes a lot of planning to figure out how best to present it in the context of the rest of the user guide. That’s before we even get to the writing part! 

So, figuring out which part of our docs requires my attention most urgently at any given moment can be a little bit gray-hair-inducing.

How do you collect feedback on your documentation to make things better?

This is one of the biggest benefits to working so closely with the support, growth, and product teams. All of the lovely customer insights and feedback that they work so hard to collect also gets onto my radar so I can use it to improve our docs. 

We also use Google Analytics to track all sorts of stats and behaviors, which helps us to see which areas of our documentation still need the most love.  

What company/product docs do you really like and why?

I have a big ol’ crush on the Wistia support docs, even though I’ve only just started playing around with their actual product. Their docs team does beautifully so many of the things I’d like to see our docs do better.

I’ve also been spending a fair amount of time with the Google Analytics docs. While I found them a little bit daunting at first, the more I use them, the more I appreciate how thorough and well structured they are. 

Finally, I really like the docs for Novlr, which is a writing tool for fiction projects. Even though their docs are pretty small-scale, and stick to an FAQ format, I think they do it well. They’re easy to filter, search, and navigate around, and they’ve got a nice, light tone to them that I find really appealing. 

What advice would you give to anyone looking to breaking into this type of work?

I’d say, first things first, join the Write The Docs slack team — it’s such a great community, and an awesome resource whether you’re just getting started doing docs or you’ve been doing it for an age. 

I’d also say, don’t worry if no one’s ever paid you to write docs before. Someone on the WtD slack just shared a story about an English teacher who started up a blog about her experiences with Git and within 3 months had landed her first tech writing gig. 

There are a lot of great ways to show off your writing chops, many of which you can do under your own power, that can be leveraged into paying client work. 

Thanks so much, Kelly!

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