Career Building in Conversational AI: Portfolios, Positioning, and Progression | With Hillary Black

Career Building in Conversational AI: From Scripts to Systems

In this episode of the CDI Expert Series: Unprompted, we sit down with Hillary Black for a deep dive into what it really means to build a career and a practice inside the rapidly evolving world of Conversational AI. As the sole conversation designer at Mav, Hillary shares how her role has grown from writing Messenger scripts to shaping product conversations, prompt systems, and design governance across an increasingly complex AI platform.

Hillary discusses the realities of startup design: collaborating with engineering and product, transitioning from scripted to prompt-based systems, and maintaining user empathy. She details challenges in versioning, modular design, and deciding the balance between generative AI and human control.

This episode covers:
- The evolution of Hillary’s role and how she navigates the intersection of design, product, and engineering
- Designing complex real-world transitions between messaging, voice, and human handoff
- Moving from scripted flows to prompt-based systems
- Why empathy and user protection remain core to conversation design
- Portfolio dos and don’ts, including why clarity beats volume
- Tailoring resumes, identifying transferable skills, and crafting a compelling career narrative
- Building a meaningful LinkedIn presence without being “always online”
- Why flexibility is becoming the defining skill for conversation designers

This episode offers an honest and actionable look at what it means to grow a career in a discipline that’s being rewritten in real time. So after listening, the question becomes: how do you build a career that evolves alongside the technology, while staying grounded in strong design principles and human needs?

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Hillary Black
https://www.linkedin.com/in/hillaryblack
Conversation Designer at MAV

What is Unprompted?

Welcome to Unprompted, a conversation series by the Conversation Design Institute, where we explore the craft, the practice, and the future of conversational AI with the people shaping it.

Learn directly from global leaders, designers, and researchers who are shaping the future of Conversational AI. Each episode of Unprompted brings candid insights, practical lessons, and behind-the-scenes stories from the people building today’s most impactful AI experiences.