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Home ›› Interviews ›› 13 Conversation Design Pivoters Share Their Stories and Advice for Breaking Into the Industry

13 Conversation Design Pivoters Share Their Stories and Advice for Breaking Into the Industry

by Hillary Black
19 min read
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I’ve never met two conversation designers who share the same background. In this emerging design discipline, there are many skill sets and unique experiences that help make someone a strong designer.

Personally, my career background is in social media and copywriting. Writing for social media and my work in marketing has always felt like a valuable asset in my work as a conversation designer, but oddly enough, none of the designers I interviewed had this background.

I’ve asked 13 conversation designers from a wide range of backgrounds to share how they found their way to a career in conversation design, how their unique skills and experience help them on the job, what their learning process has been like, and advice for anyone hoping to make a career pivot.

Before we get into the stories, I’m curious to learn even more about how conversation designers get into the field.

I’ve teamed up with UX Magazine and Rebecca Evanhoe to create a career survey for conversation designers, and we need your input!

➡️ Share your career backgrounds with us in this survey. ⬅️

Now, let’s meet the designers who will be sharing their stories…

Oluwabusayo Adeniyi, Customer Service Representative turned Conversation Designer

Fiona Daglish, Sales Manager turned Chatbot Conversational Designer at Hewlett Packard

Marlinda Galapon, Nursing Student turned Knowledge Engineer at Yahoo!, turned Principal Conversation Designer at Zendesk

Maria Karamihaylova, Speech-Language Pathologist (SLP) turned Conversational AI Designer at Microsoft

Calvin Lee, Occupational Therapist turned Conversation Designer at Amwell

Soo-Jin Lee, High School English Teacher turned Senior Conversational AI Content Strategist at Wells Fargo

Olivia Marrese, Doctoral Linguistic Researcher and University Instructor turned Senior Conversational Designer at Quiq

Pallavi Patke-Mujumdar, Adjunct Faculty Lecturer, turned Copywriter and Interior Stylist, turned Experience Designer at Comcast

Annette Raab, Program Manager, Client Communications tured AI Conversational Designer at Home Depot

Courtney Rams, Speech-Language Pathologist and Assistive Technology Specialist turned Conversation Designer at Stella Automotive AI

Boris Slesar, UX Writer turned Conversation Designer at CSOB

Joanna Szulc, Digital Sales Agent turned Product Owner for Conversation Design at Hewlett Packard

Lorian Taylor, Lead Game Artist turned Senior Conversation Designer at Cetene Corporation

How did you first learn about conversation design, and what about it drew you to pursue the field?

Fiona Daglish: I was first introduced to the concept of conversation design from a previous manager who had a real gift in understanding people. When I spoke with my now current manager, we hit it off and talked for ages…you could say the conversation flowed! What drew me in even further was the challenge of learning something new but also the excitement that I could genuinely bring something to this role, given my past experiences. I could use what I’ve already learnt to make a difference. As I learnt more, I wanted to discover more and it gave me a real passion for it and I couldn’t stop reading, watching and taking it all in.

Marlinda Galapon: I had my first experience (one-off project) working in this field at Yahoo! in 2015, when the company decided to put chatbots on Facebook messenger. They asked for people to volunteer for the project. And ever since then, I was searching for chatbot related roles (Chatbot writer, Chatbot content strategist). My job title at the time was Knowledge Engineer.

What I liked about the work, is that it combined all the things that I loved — design, strategy, linguistics, psychology, writing, service, all in one job.

It wasn’t until 2020, that I was able to land a role as a Conversation Designer at Adobe. It took me 5 years to pivot, trying to convince recruiters that my health science degree, and my job experience was relevant.

Maria Karamihaylova: I discovered conversation design while pursuing a degree in Computational Linguistics. At that time, I was planning to pivot from my previous career in speech-language pathology to the conversational AI industry — I just didn’t know in what capacity yet. I knew I wanted to leverage technology to improve human communication at a larger scale. I also knew I enjoyed the language analytics/diagnostic component of my first career. During my job search, I came across conversation designer job descriptions and realized this role perfectly synthesized my interests in language and technology and aligned with my career goals.

Courtney Rams: I spent many years as a speech therapist, with a strong focus on AAC (Augmentative and Alternative Communication). My fascination with technology and communication led me to an internship with a company called Voiceitt. Voiceitt has created speech recognition technology capable of understanding non-standard speech patterns, including those of individuals with speech disorders.

During my time at Voiceitt, I stumbled upon a newfound passion — conversation design! Witnessing the impact of voice technology on the future and the possibilities it creates sparked my interest to join the field.

Lorian Taylor: I first learned about conversation design while working at Amazon and had the opportunity to work with a couple of veteran conversation designers on a project. I was really excited about it as a new way to interact with technology and that so much of it was, and still is, undefined in terms of patterns and best practices. It was interesting to see them think about how people speak naturally and how to create a conversation with technology that works when people can say anything.

What skills or traits from your previous roles do you think best translate or give you an advantage as a conversation designer?

Maria Karamihaylova: My previous role as an SLP prepared me immensely for the less technical aspects of my new career. I had developed a solid foundation in “soft skills” that are fundamental for any conversation designer: documentation, client advocacy, prioritization, problem-solving, and cross-functional collaboration. I was already completing CxD tasks in my day-to-day role as an SLP, including:

  • Treatment planning → product roadmapping
  • Caregiver/patient interviews → requirements gathering
  • Diagnostic evaluations → conversation analysis, intent identification
  • Managing a caseload of patients → Managing multiple customer accounts across varying project lifecycles

Calvin Lee: I’ll share two perspectives since I kind of pivoted twice:

  1. In my current role as a conversation designer at Amwell, a healthtech company, my background as an occupational therapist (OT) plays a significant role in shaping my design and research approaches. Leveraging my experience working with healthcare consumers and adhering to health literacy standards has been invaluable, especially since the conversations I design are intended for patients, caregivers, and clinicians. My goals have always been centered around creating meaningful experiences, and to do that now by curating human narratives is so fulfilling.
  2. My previous experience in product ops/content design helped me recognize the importance of clarity and accessibility in content, as well as setting processes in workflows. That experience taught me how to strategically simplify complex concepts into understandable language, while also growing as a leader and collaborator when working with cross-functional teams — both crucial aspects of conversation design. The skills I honed within this role seamlessly translate into my work as a conversation designer every day.

Overall, I’m grateful to have my previous roles as part of my identity. I believe that conversation design is a field that demands a diversity of skills, from a designer’s aesthetic sensibilities to a clinician’s empathy for the end user, allowing me to thrive in my conversation design work.

Soo-Jin Lee: I got into playwriting because I have a natural ear for dialogue. Writing pithy, strong dialogue was something my fiction friends noticed. Users enjoy when conversational products are well-written with that human touch. As for my classroom experience, I learned quickly what keeps students awake. Storytelling that’s engaging. Humor. Drama. Emotions. Also, teaching is improv. You learn how to persuade a crowd to care about something and learn about it. Teenagers are possibly the toughest crowd.

Pallavi Patke-Mujumdar: Information organization, critical thinking and writing, attention to detail, analytical skills, marketing, copywriting, leading with a vision, iterative approach to design.

Annette Raab: I had a decade of writing and content experience, UX training, and a graduate degree in technical communication before pivoting to conversation design. This background and education seemed like a natural fit for conversation design. It also helped that I already understood the inner workings of large corporations, which were the types of employers I was going after.

Boris Slesar: Practicing empathy with the user, being a good listener, always asking additional questions to get to the heart of a matter, and cultivating the skill of designing texts.

Joana Szulc: Having a great knowledge of customer support in digital world. I was working for 4 years as a chat agent. I was aware about customer pain points, how to chat with customers, using the right words. I was also a trainer for many years and I had acquired an extensive product and brand knowledge. I also had the experience of how everything works on the backend, from the operational point of view. This was also one of my objective, how to give to our team more qualitative conversations and providing a great self-service.

Lorian Taylor: When I worked in games the titles I worked on all had a story, a narrative, that gave players something to keep them going. I wasn’t a script writer for them though, I was creating the gameplay environments. When I created those environments I had to think about how the visuals supported the story. How the lighting might help players know where to go. I later transitioned from games to user experience design which gave me a foundation in solving problems with the user and their goals in mind. I think these experiences gave me a way of viewing everything as a conversation, or journey, between the thing I’m making and the end user. I think that has helpful to my role now, even though creating game art, or designing an app, isn’t a literal conversation.

Once you decided you wanted to be a conversation designer, what did you do to learn the skills?

Oluwabusayo Adeniyi: I took up the Introduction to Conversation Design course with Voxable, took Hillary Black’s 14 Days Conversation Design challenge, went through Google’s YouTube videos on conversation design as well and read articles and developer documentation by Google. I also connected with a lot of conversation designers on LinkedIn and joined virtual Conversational AI events. I also sourced mentors and joined many communities for women in tech. Over time, to continue to upskill, I have been in mentorship with Joti Balani, worked on some volunteer international projects, and also taken courses with Conversation Design Institute. I still read blog posts and I recently started listening to podcasts.

Marlinda Galapon: Once I realized this was the job I wanted, I dove into books, I created portfolio with my Yahoo experience, and started following people who were already in the field. One thing I knew I lacked was the UX terminology, and communicating design decisions. Since I had no formal training in this space, I definitely did not come across as confident, even though I knew I could do the work. I also cleaned up my LinkedIn, so that my profile would be found.

Soo-Jin Lee: My friend who introduced me to conversation design suggested I take the conversation design course at Conversation Design Institute. She didn’t take it herself but noticed good things being published by them. I also attended 2 virtual conferences last summer so I could meet mentors, influencers (like you, Hillary), and friends. You need friends in any field. I also picked up 2 short-term contract gigs before I got my enterprise offer. Also, over 4 months, I had 29 informational interviews. Each person I spoke to taught me something about the field and that was valuable. I learn best one on one. I love the Socratic method. I broke into the field by going through various points of entry.

Maria Karamihaylova: Once I knew I wanted to pursue a career in conversation design, I started to absorb all the free/low-cost information and training that I could find online. I read blogs and joined various CxD groups (shout out to all the resources Hillary organizes!). Diana Deibel & Rebecca Evanhoe’s Conversations with Things and Cathy Pearl’s Designing Voice User Interfaces were essential reading. I completed several trainings to learn about conversational AI frameworks (Dialogflow via Coursera, Cognigy’s Conversation Design course, etc.). I also explored design tools such as Figma and Miro. Finally, I connected with folks on LinkedIn who had successfully pivoted to careers in CxD (including a couple of former speech-language pathologists whose guidance I’m deeply grateful for). If I had to do it all over again though, I’d more actively focus on developing a portfolio.

Olivia Marrese: One of the most important things I did was create a UX-style portfolio to showcase my work. Sometimes I would have a conversation with a recruiter or hiring manager that seemed a little lackluster, until they saw my portfolio, and that’s when I got interviews.

Annette Raab: I signed up for a chatbot course with UX Content Collective. I also searched the web for everything I could possibly find on the practice of conversation design, and read “Conversations with Things,” which is an excellent introduction to conversation design practice.

Courtney Rams: Once I found out about conversation designer I embraced this field, actively engaging in online communities, participating in mentorship sessions and enrolling in bootcamp-style courses to sharpen my technical skills. I developed a conversation design portfolio and started applying to jobs.

Joana Szulc: Before designing our first chatbot, I spent a lot of time analyzing other chatbots. Webinars were very helpful at the beginning and participation to few Bot summits were enlightening. I was trying to grab tricks and tricks from everyone.

The most of my time was dedicated on conversations reviews. If you want to learn how your customers are interacting with your Bot, you have to work intensively on your data. I’ve reviewed a thousand of conversations, analyzing in depth the conversation flow.

I’ve learned that there are no magic patterns for a great design, it’s so specific to your industry or to your personas. You need constantly to think about novelties and how you can enhance the customer experience. Not being afraid of new technologies like AI but thinking how it could be useful for your customer.

How did you find your first role as a conversation designer?

Maria Karamihaylova: I applied to MANY jobs, all the while networking and learning as much as I could about the conversational AI industry. I spent far too much time on LinkedIn! I finally landed a contract position as a Conversation Analyst; I had the opportunity to gain hands-on experience learning about generative AI, language model training, and intent classification through the lens of data annotation. This contract job was pivotal in making me a desirable candidate during the interview process for my first role as a designer because by then, I had relevant experience in the field.

Calvin Lee: Through LinkedIn! LinkedIn and Glassdoor were my main go-tos when I was on the searching for new opportunities. My current role just appeared on my LinkedIn job feed, so I submitted my application that way. I also learned a trick to type “hiring conversation designers” into LinkedIn’s search bar and then filter the results to show posts shared within a specific time frame. The results would sometimes show if any hiring managers or recruiters had posted about openings that might not have been officially listed in the job roster yet. Shannon (Sullivan) Leahy is also a great resource to follow! I’ve followed her since my content design days, and she actively shares all kinds of new content job listings, including those in conversation design.

Soo-Jin Lee: I quit all social media except Linkedin. It became my Tinder. I was on it first thing when I woke, and it was the last thing I scrolled through before falling asleep. So I could keep up with the freshest job postings. In August, I saw a role at a bank with the exact title I was looking for. I messaged the hiring manager right away. She responded right away, too. Had no idea who I was and told me to go ahead and submit my resume. I felt encouraged by that. After submitting my resume through the company portal, I let her know. She said she would look out for my resume. She did. Two days later, a recruiter called me and then began my rounds of interviews. The hardest interview was the portfolio walk through. I was asked a ton of questions I didn’t feel like I had the “right” answer to. I did my best. Phew. And got the job offer.

Pallavi Patke-Mujumdar: Through your [Hillary] job board, ConversationDesignerJobs.com, plus a mutual connection.

Annette Raab: I was extremely fortunate in that a recruiter reached out to me, but I did have my LinkedIn profile and resume ‘optimized’ for conversation design.

Olivia Marrese: Lots of conversations with people in the field to find out who was hiring and what sorts of skills they were looking for. Folks in this field are incredibly generous with their time, and I’ve made a commitment to be equally helpful with people just starting out.

What was your biggest challenge during the job search or interview process?

Oluwabusayo Adeniyi: I have been searching for more conversation designer opportunities and challenges and I must say it hasn’t been a bed of roses. My biggest challenge so far is companies searching for unicorns as their conversation designers. They want someone with programming skills in addition to their conversation design skills. Many also want designers with 4+ years of vast experience in NLU/NLP. For a field that just emerged a few years back, the requirements seem quite ridiculous.

Fiona Daglish: The biggest challenge during the interview process was to make sure I conveyed all the relevant experience I’d gained, that would be useful for the new role. I was changing industry and venturing into something totally new so I wanted to make sure I gave my (now) manager an insight into what I could bring to this new team and role. As I’m sure a lot of other conversation designers struggle with, there’s never a shortage of words so I had to try and not waffle!

Calvin Lee: The biggest challenge for me was convincing employers to give me a chance and to believe in my abilities. The hiring scene has always been a bit of a rollercoaster, and it can get even wilder for career pivoters. I attribute much of what I bring to the table to my time in grad school and caring for patients as an occupational therapist — an identity that will stay with me whether I’m working in the health space or not. Think about all that comes with being a clinician: the collaboration, research, planning, strategy, and leadership — the list goes on! Yet, I’ve encountered scenarios of folks discounting my skills, thinking they don’t quite fit the ‘right’ context, which made me believe I had to start fresh to avoid that bias. However, I’ve since learned to reframe my experiences and embrace them to align with the skills needed for the roles I pursue. Career pivoters are unique individuals who come from a diverse range of backgrounds. It’s all about leveraging what we’ve got to find perfect match!

Olivia Marrese: During my initial job search, I was anxious that I hadn’t yet done enough to prove how valuable I could be. Making the jump from academia, a very different field, was intimidating, and I had to continually remind myself that I was qualified. I also spent a lot of time learning the language of the tech industry; even things as simple as calling slides a ‘deck’ and not a ‘powerpoint’ show that you have done your research.

Annette Raab: The process for me this time wasn’t difficult. But my pivot into UX, before getting into conversation design, was extremely challenging. The best advice I can give is to be persistent and do everything you can to gain the skills and knowledge you need. And don’t be afraid to network. Sometimes people are busy and can’t connect with you, but there will be people who are happy to help.

Courtney Rams: My most significant challenge during the job search and interview process for a conversation design role was the lack of transparency and consistency in the field. I encountered various titles for similar roles and noticed that companies advertised these positions differently. Some required more extensive coding skills, blurring the lines between true conversation design and other related roles. Additionally, the actual responsibilities and expectations for conversation designers varied significantly from one company to another and has changed over the past year with all the advancements in generative AI.

Another notable challenge was the significant pay discrepancy within the field. While I understood that transitioning to a new career might involve a potential pay cut, I struggled with the lack of clarity regarding salary expectations for entry-level designers. This lack of standardized compensation made it difficult for me to negotiate effectively or determine what constituted fair compensation for my role and skills.

Boris Slesar: When I worked on the test assignment, I wasn’t in the clear as to what was expected of me, so I went a little over the top and made it too complicated. Now I know better (namely, I’m better at Voiceflow).

Lorian Taylor: At the time when I let my manager know I wanted to take on conversation design for Amazon Kids the biggest challenge was getting out of my own head and not letting impostor syndrome, “but you’re not a REAL conversation designer”, hold me back. In my most recent job search the biggest challenge was that many places hiring conversation designers don’t really know what the role is or what we do. It’s a role places now know they need someone to do, but don’t know how to write job descriptions or interview for.

What one piece of advice would you give to aspiring conversation designers coming from a unique background?

Oluwabusayo Adeniyi: Your skills are TRANSFERABLE! Never sell yourself short or think your previous skills are irrelevant. They are very relevant to the field of Conversational AI.

Never stop learning! This field is constantly evolving, there are new developments every day! One day all the knowledge gained will pay off.

Also, DON’T give up. It might take some time to land a role, especially with seemingly few jobs being available but keep honing your craft and you’ll get it when you least expect it.

Fiona Daglish: I think my overall advice would be to ‘create with purpose!’ Don’t be afraid to make mistakes, generate ideas but also learn when to stop, when it’s enough and don’t over complicate things. Give your mind time to create but always keep your customer at the heart of everything you do.

Marlinda Galapon: Do your research, and have questions ready to ask about how the company you’re interviewing with is solving a particular problem for their digital assistant — even better, if you can test their product and mention what you think could be improved. This will show your knowledge in the space. Rather than getting stuck in trying to connect the dots between where you came from, start first with showing how you can add value.

Maria Karamihaylova: Accept and embrace the idea that your career trajectory won’t be linear. Conversation designers have varied educational and professional backgrounds, including in UX, the arts, computer science, education, and more. I’d argue every conversation designer comes from a unique background and brings a distinctive skillset that adds value to the industry. You’re in good company!

Calvin Lee: Embrace your unique perspective as a valuable asset! Your experiences, skills, and insights can set you apart in conversation design. Instead of conforming, leverage your individuality to bring fresh, innovative perspectives to the table. Whether you’re a UX designer, linguist, clinician, teacher, or in ANY other profession, cherish your background as a source of creativity and a means to stand out in a rapidly evolving field.

Soo-Jin Lee: I liken job hunting and the interviewing process to dating. It can get grueling and discouraging real fast. But the right role is worth waiting for. Know that every interview you have is a rehearsal for THE interview you want to make a big difference in.

Olivia Marrese: I firmly believe that our unique backgrounds make us stronger as conversation designers. Being able to see things from multiple perspectives is a huge asset when working on brand-new technology, because we’re used to questioning the status quo.

Pallavi Patke-Mujumdar: Certification programs are worth it, if it helps you build new and essential skills and if you are able to find a mentor. Both these factors make a huge difference in giving you the edge, especially if you lack a good network or closely associated academic qualifications.

Annette Raab: Look at job descriptions and highlight all of your experiences and skills that align to conversation design roles, and be sure to experiment with Voiceflow or other tools to create a portfolio piece, such as chatbot — a bot incorporating generative AI and LLMs if you can!

Courtney Rams: My advice to aspiring conversation designers coming from a unique background would be to embrace the opportunity and go for it. You likely possess a wealth of skills that are transferable to the field, so don’t underestimate yourself or fall victim to imposter syndrome. Instead, gain confidence in your abilities and focus on leveling up your skills. Additionally, don’t underestimate the power of community and networking. Engage with others in the field, seek mentorship, and build connections to accelerate your growth and open up new opportunities. Your unique background can be a valuable asset in conversation design, so own it and use it to your advantage!

Joana Szulc: Emphasizing your soft skills is the key. My team is a mix of journalist, teachers or UX designers.

Boris Slesar:

  1. Always ask additional questions.
  2. Conversations can usually be simplified. Trim your conversations whenever appropriate.
  3. There is incredible value in familiarity. Create familiar patterns whenever you can.

Lorian Taylor: I’d say not to let your background stop you from pursuing conversation design. Things are evolving and changing so fast I see it like how web design was in the 1990s. People are coming to conversation design from so many different disciplines I have yet to meet someone whose prior experience didn’t help them out in some way.

A big thank you to all of the conversation designers who were so open and honest with me about their journey into the field. When changing careers it can feel intimidating, overwhelming and sometimes, overly difficult, but this community has continued to be welcoming, insightful and giving to newcomers. I encourage any aspiring conversation designer to go for it, and that advice will never change!

If you’re a conversation designer — what’s your background? Myself, UX Magazine and Rebecca Evanhoe are interested in hearing from pivoters and conversation designers, with plans to share our research results with our industry.

➡️ We’d appreciate you filling out our career survey! ⬅️

post authorHillary Black

Hillary Black, Hillary Black is a conversation designer, marketer, content creator, etc. based in Southern California. After 10+ years in social media she brought her passion for creating brand personas to bots and never looked back. Today, she’s the head of design at Mav, founder of Conversation Designer Jobs and host of the Conversation Designers Internet Club community on Facebook and Twitter. She’s a contributor to Amazon’s Discover.bot and regularly shares her insights on CxD at events.

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Ideas In Brief
  • The article features insights from conversation designers, detailing their diverse backgrounds, learning paths, and challenges in the evolving field, offering valuable advice for aspiring professionals.

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