Career Building in Conversational AI

Write your awesome label here.

Hillary Black joins CDI’s Rachel Whitehorn to unpack how conversation design roles are evolving, from scripted flows to prompt-based systems. She shares practical insights on portfolios, career positioning, LinkedIn presence, and the skills designers need to stay adaptable in a fast-changing AI landscape.

In this episode of Unprompted, Hillary Black joins CDI’s Rachel Whitehorn 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.

Across the conversation, Hillary opens up about the realities of designing in a startup environment: collaborating with engineering and product teams, orchestrating the transition from scripted flows to flexible prompt-based systems, and maintaining empathy for users in sensitive, high-touch scenarios. She also reveals the challenges that come with versioning, modular design, and determining where generative AI should “take over” versus where humans still need tight control.

The episode also explores Hillary’s work beyond her day-to-day role—reviewing hundreds of portfolios, advising candidates on breaking into CxD roles, and helping emerging designers build a presence that supports real career opportunities. From discussing the value of personal branding on LinkedIn to the common mistakes she sees in portfolios and resumes, Hillary gives grounded, practical advice for designers at any stage.

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 and why that shift is challenging at every level
Why empathy and user protection remain core to conversation design
Portfolio dos and don’ts, including why clarity beats volume and why video demos belong at the top
Tailoring resumes, identifying transferable skills, and crafting a compelling career narrative
How to build a meaningful LinkedIn presence without being “always online”
Why flexibility is becoming the defining skill for modern conversation designers
Whether you're entering the field, evolving your role, or leading Conversational AI teams, 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.

Hillary Black is a conversation designer, marketer, content creator, and community builder who’s been leading the conversation design and brand efforts at Mav, an AI-powered SMS assistant for lead generation. Hillary is also the founder of Conversation Designer Jobs and the Conversation Designers Internet Club, and she serves on the UX industrial advisory board at the Milwaukee School of Engineering.