Manager – AI Conversational Design

About the Role

At Pearl, Conversation Design shapes AI experiences that help millions of customers every day. As our Manager, AI Conversational Design, you’ll lead a team of Conversation Designers and partner with Product, Engineering, Analytics, and AI teams to improve those experiences at scale.

You’ll coach and grow your team, stay close to the work, and own initiatives that advance Conversation Design. This role offers room to build, experiment, and influence where the discipline goes next.

What You’ll Do

• Lead, coach, and develop Conversation Designers through feedback, career support, and thoughtful prioritization.
• Hire and onboard new team members as the organization grows.
• Partner across Product, Engineering, Analytics, Machine Learning, and AI to deliver effective conversational experiences.
• Own a strategic initiative, such as improving evaluation, tooling, workflows, or quality practices.
• Use AI tools, experimentation, and customer insights to help the team work more effectively and improve its output.

What We’re Looking For

• Experience leading and developing teams in Conversation Design, Conversational AI, or a related field.
• Hands-on experience building and shipping conversational AI products or LLM-powered agents.
• Experience improving conversational quality through evaluation, optimization, experimentation, or A/B testing.
• Strong cross-functional partnership and the ability to turn strategic ideas into practical improvements.
• A collaborative, curious leadership style and confidence using AI tools in your daily work.

Why You’ll Love This Role

You’ll help define how Conversation Design grows at Pearl while developing talented designers and staying close to meaningful product work. You’ll have the autonomy to test ideas, improve how the team operates, and shape AI experiences used by millions of customers.

Remote From these States: California, Florida, Georgia, Idaho, Illinois, Massachusetts, Michigan, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Texas, Virginia, Washington, and Wisconsin.

Pay Transparency: Pearl will provide pay transparency information upon application to those in qualifying jurisdictions. (Employment is with JustAnswer LLC, a Pearl company.)