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How to Get Hired in Conversation Design Part 1

Tips to help you land your first job as a Conversation Designer

This is part 1 of a 2 part blog series! To skip to part 2, check out this link!

Conversation Design is the most exciting variant of UX Design out there. It’s nascent, niche, and extremely fast-growing with more companies wanting to take advantage of the power of Conversational AI every year. Fortunately, for any aspiring conversation designer out there, it means that this is still the best time to get started in the field. Unfortunately, for any aspiring conversation designer out there, it also means that any information on how to enter into the industry is still quite limited and, most of the time, outdated.

While Conversation Design is a unique specialization under the UX umbrella, many, if not most, tips about interviewing for UX Designer jobs do not apply directly to Conversation Design jobs. On top of that, much of the advice on how to get into the industry may come from professionals who have already been working in the field for a handful of years. If you just want a no-nonsense, clear outline on how to get your first job as a Conversation Designer, look no further.

I interviewed four different Conversation Designers to find out what tips & tricks they’ve used to learn more about the field and, more importantly, get hired. All of the people I’ve interviewed here have been at their current role for less than a year. Let’s meet them.

Our 4 CxD professionals

Let’s welcome our 4 generous & talented conversation designers!

Feel free to connect with them on the following channels:

Brittany Neal, LinkedIn and Twitter
Kevin Pichinte, Linkedin
Julia Anderson, LinkedIn, Medium, and Twitter
Austin Bedford, Linkedin and Twitter

And now let’s get to the questions! :)

What is your current job title and company?

Brittany: Conversation Designer at Wix

Kevin: Part-Time Conversation Designer for Simple App; I’m also a SEO content strategist for Greenlane

Julia: Contractor at Samsung Research America as a Conversational UI Writer

Austin: Conversation Designer Senior at Salesforce

What kind of jobs have you done before?

Brittany: Project Manager at TransPerfect Translations → NLP Software Engineer Intern → NLP Software Engineer at Midea → Conversation Designer at Wix

Kevin: Digital journalism & TV broadcast writer (think NBC, Telemundo, ABC) → UX writer→ Content Strategist and Conversation Designer

Julia: Healthcare consultant → UX Designer → Conversation Designer. I’ve worked at a large corporation, a startup, and companies in between.

Austin: Healthcare Billing Specialist → English Teacher in China → UX Designer → Product Designer → Conversation Designer

How long were you on the job hunt?

Brittany: Casually for 3 months.

Kevin: Technically speaking, I was on the job hunt for a while, but it really started almost a year ago. I started taking UX writing courses, really getting involved and taking on more projects. It took like 9 months to land a legit job, not just projects.

Julia: I was on the job hunt for about 6 months doing freelance work and design gigs before landing my current role.

Austin: For probably a good year.

What resources or job boards did you use to find open Conversation Design positions?

Brittany: LinkedIn — I was actually too intimidated to apply to Wix, but then was reached out to by an exceptional recruiter. Also hearing about opportunities from the Voice Community.

Kevin: It really was just networking with people in the industry and talking with different professionals. I joined the Facebook group by Hillary Black, Conversation Designer Internet Club. Hillary just happened to put out a CD role in her group and I messaged her, passed along my resume, and the rest is history (I got the job).

Julia: I subscribed to LinkedIn, Indeed, and ZipRecruiter job alerts for “conversation designer.” I also regularly checked Hillary Black’s conversationdesignerjobs.com. Beyond these, I kept an eye on my LinkedIn network and various industry contacts who knew about jobs that were not widely posted.

Austin: So I was applying and just trying to have informational interviews. The Salesforce position was due to an informational interview. Honestly, not even looking for jobs first works. I think a lot of people like to talk about their own work. If you can show that you’ve been interested in their work when you have these informational interviews, they may tell you about an opportunity that’s not even listed. Some percentage of jobs are never posted online.

If you can show that you’ve been interested in [someone’s] work when you have these informational interviews, they may tell you about an opportunity that’s not even listed.


When did you feel your resume and/or portfolio were finally “ready” for job applications?

Brittany: When I had all the projects I’d worked on appropriately represented on my resume… My portfolio is still not exactly aggregated. It’s far more important to be able to talk about the work you’ve done and the skills that you have than to worry about showcasing them. I do have a chatbot on my personal website that definitely does not represent my experience as a Conversation designer, but I figured, “Hey — it’s a chatbot!”

quick tip, brittany’s quote. It’s far more important to be able to talk about the work you’ve done and the skills that you have than to worry about showcasing them.

Kevin: I have a friend who’s a UX Researcher. He helped put my resume together early on, so I didn’t really have to struggle with that. In regards to my portfolio— that’s something that I haven’t officially put together, but I do have snippets of UX writing samples and Conversation Design samples that clients can look at. They’re under NDA though, so I can only share them with clients. I never actually had that moment of, “Oh, I feel ready.” I just share my stuff, we start interviewing, then they see my potential and what I can actually do.

Julia: My resume was completed before my portfolio. Once I had a couple deliverables from my UX design roles that I could speak about in interviews, my resume was ready. My portfolio was and continues to be a work in progress. I applied to jobs while I improved my portfolio, but I didn’t begin applying until I had 3 case studies available.

Austin: Because the industry is fairly new, I think one really good (case study) is good. I was aiming for two. I would show the prototype that I had from a Stanford case study, but it was kind of a weird project because of COVID. You know, building something for COVID during COVID; it wasn’t quite complete. But, I did have the Pagers chatbot that was complete, so I was able to talk about the users, the chatbot, as well as our workflow.

Check out Austin’s portfolio website here.

Did you have to complete assessments for your interviews? If so, how were they?

Brittany: Yes — Wix has a monster of an assessment. But it’s a fun test that we do go over thoroughly. I never came across an assignment from applying to a conversation design job that I wasn’t eager to do. That was another way I knew I’d found my passion, I couldn’t get enough of it!

Kevin: Again, I was introduced to Simple through Hillary Black. She introduced me to them and then the next step was creating a full conversation for a chatbot. Initially, I created the sample dialogue, then eventually the actual script and implemented it, following their content style guide— whatever they had at the moment because that’s constantly developing and changing. It was definitely a test. I had to write a whole script, show them my process, and explain it to them. They liked it. They actually used the script I did for my test.

Julia: I had one assessment for my interviews, but typically had standard one-on-one or panel interviews throughout the hiring process. The one take-home project was for a UX writing role and I had to optimize microcopy for several screens and justify my changes. It was a great design exercise that inspired me to continue applying for roles that emphasized writing.

Austin: No, I pretty much had two informal interviews with my boss. I dread assessments— they’re so annoying because you don’t know a whole lot about the company and you have to make a lot of assumptions.

What was the hardest step in the interview process for you?

Brittany: Wix’s interview process was actually a ton of fun. I felt that I’d found my niche based on how much I enjoyed the chats. The hardest part was the preparation, and actually applying.

Kevin: I guess the hardest part is when they ask you a question and you have to think quick on your feet. I’ve had those instances where they ask, “How would you track that this is going to be successful?” and it’s kind of hard to give an answer because every project is different. The goals are different. Sometimes people will say, “Oh, you got to do A/B testing or you got to do this,” and it’s like “well, not necessarily — hold up.” So, I think the hardest part for me has been questions I didn’t think about but I have to pull from my experience to answer as best as possible.

Julia: During interviews, I had to prove that I understood conversation design despite having limited real-world experience. Crafting a story around this was difficult, but my advice is to demonstrate curiosity and passion during your interview. I explained how my past experiences complimented my newfound career and provided concrete examples wherever possible. At the end of the day, an interview is a conversation and trusting your conversation skills will make a huge impact.

Austin: I didn’t know what to expect. During most of the interviews I did, I was really stressed out. Some of them would go up to 5 rounds, so I explained my work about 5 times. There was one with a 2 hour test. For this one, I really didn’t know what to expect because it was less rigorous and it was less formal.

How did you find out about where to price your compensation? Did you reference figures for another job titles, and if so, which?

Brittany: I did some Google searching, and some Glassdoor research, but it’s such a new field with varying titles that it was difficult to get a good sense. I compared it to technical writing and already had a sense of what was going for NLP software engineering.

Kevin: My main reference was asking people in the field. Like, “How much does it make sense — at my given experience — to charge,” and everyone gave me relatively the same ballpark. I knew I had to make sure, aside from just researching, to ask actual professionals what they were earning at the top cities like New York, LA, San Francisco, and Seattle. I also looked into how much people were earning in LA, so there was definitely a certain rate I wouldn’t take.

Julia: I used Glassdoor to find compensation for conversation designers and UX writers in my area and with my experience level. I also asked colleagues in the industry who were early in their career to gauge if I was valuing my work fairly (and not underselling myself!).

Austin: Glassdoor is definitely my friend. Being in San Francisco, you have to know exactly what people are getting. You don’t want to sell yourself short and it’s too detrimental not to— like if you can’t afford rent.

What advice would you give to someone in their first month on the job?

Brittany: Relax. You only know what you know, and you can learn whatever else you need to know. Trust that your employer vetted you well, and are paying you for your opinions. The field is still being created, so make decisions for yourself on what is best, and what should be standard. Consume as much knowledge as possible so you can stand on the shoulders of giants and don’t have to reinvent the wheel, but also know that trying new things leads to the innovations that benefit the whole conversation design field.

Kevin: Don’t be scared. Go into it, knowing that you don’t know everything. If you don’t know something, look it up. Google has most of the answers. Also, don’t be afraid to ask questions — I mean, it doesn’t hurt. I’ve asked so many people in the field like, “How do you do this?” or “How do you do that,” and everybody helped me. That would be my main advice to anybody: don’t be afraid to just jump in. I wish somebody had told me that because I was terrified in the beginning and didn’t feel adequate to work in tech, but sometimes you have to get down and dirty to do whatever you got to do. Even if you don’t get it right the first time, it’s okay.

Don’t be scared. Go into it, knowing that you don’t know everything. If you don’t know something, look it up […] Also, don’t be afraid to ask questions.


Julia: Be a sponge. Absorb as much information as possible about your team, what they work on daily and how they collaborate with stakeholders. Ask questions whenever possible, even if they seem silly. It is better to ask “silly” questions when you first start rather than a few months in.

Within your first month, figure out how you can add the most value. That could mean being very good at your specific job requirements or lending a helping hand to a teammate. Whatever it is, ensure that you are communicating with your team regularly to understand their expectations and working styles.

Ask questions whenever possible, even if they seem silly. It is better to ask “silly” questions when you first start rather than a few months in.


Austin: I would spend the first month really understanding the product. Once you understand the product really well, then you can think about the opportunities that conversation design can offer. To do that, you have to talk to the PMS, talk to the UX Designers, and read any resources that the company may have. Definitely look at the brand too; the brand will give you the voice and tone for the conversations you’re going to be creating.

Bonus Q! Which books, articles, videos, or other resources helped you prepare for your job?

Brittany: Microcopy: The Complete Guide by Kinneret Yiffrah. The TWI technical writing workshop— I was a guinea pig for their first Zoom session they started during COVID. Cathy Pearl on Youtube and her book are great places to start.

The best resources I tapped into was the Voice Community and engaging with as many virtual meetups and discussions as I could. Attending conferences such as the Chatbot Conference and one held by Rasa (L3-AI) also got me pondering the future of Conversation Design, and the tools people were using along with the big challenges they were facing. Building a bot via Coursera’s Dialogflow course also really helped. I had already made a bot on my own by playing around with DF, but the course filled me in on some tools it offered I hadn’t known existed.

Kevin: Writing is Designing. I attended the workshop with Andy and Michael. Michael actually gave me feedback for a sample dialogue I was writing up, which was invaluable, so a huge shoutout to him. Also, Microcopy: The Complete Guide and the common books you can pick up like Cathy Pearl’s book, Designing Voice User Interfaces, or anything Google has on their website.

What’s really helpful is looking at how Conversation Design has a lot of similarities with other industries. I have a background in journalism and Conversation Design is very similar. In broadcast writing, you have 15 seconds to write a complete story— the anchor has to be able to read that like they’re having a conversation on live TV. So really, it’s all about pulling from your background.

Julia: Designing Voice User Interfaces by Cathy Pearl is a fantastic resource. I browsed several articles on Medium (some from here) and Voicebot to keep up with the news. The monthly Voice Den talks are also a great place to meet people and keep a pulse on the latest industry events.

My most important resource was my network. It is difficult to prepare for a conversation design role without understanding what it’s like to be a conversation designer. Having those conversations with colleagues proved invaluable for my interviews and current job.

Austin: Conversation Design Institute for certification because that’s what I did. Definitely Cathy Pearl’s book. Now, I would definitely put Rebecca (Evanhoe)’s book on there too. Other books, I think the Microcopy book is really good, though it’s more UI focused, and Sarah Richards’ book on Content Design. I also recently found out about Deborah Tannen. It’s interesting to hear her talk about conversational style.

A good tip that I have: if you know certain people, for example Hans van Dam, type in his name in the search bar and see which podcasts have interviewed him. It’s a good way to learn more because they don’t usually feature in just one show.

Key Takeaways

Tip #1 — Don’t be afraid to ask questions!

Tip #2 —Connect with other CxD professionals, you never know what you might learn!

Tip #3 — There’s plenty of online resources and books to learn from. Cathy Pearl’s book is an all-around fave.

About the author

Elaine Anzaldo is a conversation designer & content creator. She first entered the voice scene as a speech consultant for SRI International in 2019 and has since worked many different contract jobs at large tech companies, including a role as a metadata curator for the Siri team at Apple. Elaine’s work now focuses on designing conversational journeys for across voice and chat, with an emphasis on multimodal solutions. She often writes and shares about the realities of being a conversation designer and publishes resources to help junior conversation designers get started in the field. When she’s not thinking about bots, you can find her watching Tollywood movies and taking pictures of her cat, Caesar.

Follow Elaine on Twitter! Linkedin! Or Instagram :)



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