Career Building in Conversational AI: From First Portfolio to Product Impact

Careers in conversational AI rarely follow a straight line.

Roles evolve quickly. Tools change mid project. Job titles struggle to keep pace with the actual work. Conversation designers are often asked to define their scope while delivering production ready AI systems at the same time.

In this episode of Unprompted, Conversation Design Institute Practice Lead Rachel Whitehorn speaks with Hillary Black, Head of Brand at Mav, about what it really means to build a career in conversation design as the discipline continues to evolve.

“Conversation design today isn’t just about writing flows. It’s about designing systems that can adapt while still protecting users.” -Hillary Black

Drawing on seven years inside an AI product company and years mentoring emerging designers, Hillary offers a grounded perspective on how conversation design roles are shifting from scripting toward product impact, governance, and long term system thinking.

Hillary Black | Head of Brand at Mav | Conversation Design Content Creator

Hillary Black is a conversation designer, marketer, and community builder leading brand and conversation design efforts at Mav, an AI powered SMS assistant for lead generation. Over the past seven years, her role has grown alongside the product, from writing early Messenger scripts to shaping product conversations, prompt systems, and design governance across a complex conversational AI platform.

Beyond Mav, Hillary founded Conversation Designer Jobs and the Conversation Designers Internet Club, where she supports designers entering and advancing in the field. She also serves on the UX Industrial Advisory Board at the Milwaukee School of Engineering, helping connect industry practice with education.

“The work changed as the product changed. What started as dialogue writing became product thinking very quickly.”

Rachel Whitehorn | Practice Lead, Conversation Design Institute

Rachel Whitehorn is the Practice Lead at the Conversation Design Institute, where she works with designers and organizations building real world conversational AI systems. Her work focuses on applied conversation design, product strategy, and helping teams navigate the realities of designing for AI at scale.

As host of Unprompted, Rachel brings a practical, systems oriented lens to conversations about how conversational AI is built and how the people behind it grow in their roles.

As the only conversation designer at Mav, Hillary is responsible for maintaining conversation quality at scale without the support of a large design organization or mature tooling.

She discusses the challenge of moving from dialogue first design to modular, prompt based systems, including:

• Managing prompts, scripts, and conversation logs
• Handling versioning and experimentation
• Deciding where generative AI should lead and where human control is essential

“The hardest part isn’t generating language. It’s deciding where flexibility is helpful and where it becomes risky.”

In small teams, governance often lives inside the designer’s head. Hillary emphasizes the importance of building shared understanding across teams, even when formal systems don’t yet exist.

Through Conversation Designer Jobs, Hillary has reviewed hundreds of portfolios and she is clear about what hiring managers actually notice.

Strong portfolios prioritize clarity over volume. They explain why decisions were made, not just what was designed. They make it easy to understand a candidate’s thinking quickly.

“If I can’t understand your reasoning in the first few minutes, it doesn’t matter how many screens you designed.”

Hillary also challenges the idea that only real client work counts. Well structured sample projects can be just as effective when they clearly show problem framing, constraints, and outcomes.

Short video walkthroughs, she notes, are often the fastest way to communicate thinking, especially for conversation design roles.

Hillary is well known in the conversation design community, but she is careful to separate visibility from constant content production.

In the episode, she and Rachel discuss what actually helps designers get noticed:

• Clear LinkedIn profiles that explain how you think
• Occasional, intentional sharing over frequent posting
• Making reasoning visible, even without many projects

“You don’t need to be loud. You just need to be clear.”

For many designers, a small, consistent online presence is enough to support real career opportunities without turning LinkedIn into a full time job.

As conversational AI continues to evolve, Hillary reflects on which skills remain essential and which are fading.

While prompt engineering has gained attention, she sees it as part of conversation design, not a replacement for it. The fundamentals, empathy, systems thinking, responsibility, and judgment, still define strong work.

“Good AI products won’t win because they talk more. They’ll win because they know when not to.”

Looking ahead, Hillary believes adaptability will be one of the most important skills for conversation designers, both technically and strategically.

This post highlights key themes from the conversation, but the full episode includes deeper examples, practical stories, and candid reflections.

Watch or listen to the complete episode of Unprompted with Hillary Black, embedded below.

Whether you are entering the field, evolving your role, or leading conversational AI teams, this episode offers an honest look at what it means to build a career in a discipline that is still taking shape.