Manager, AI Conversational Design

About Us
Pearl is AI for professional services at global scale, combining advanced AI with verified human expertise to deliver help that is accurate, accountable, and fast. Since 2003, our network has connected millions of customers with licensed professionals across 196 countries, making real expertise available anytime, anywhere.
Our Values
Data driven: Start with truth, measure what matters.
Courageous: Bias to action; run toward hard problems.
Innovative: Seek novel, elegant solutions.
Lean: Do more with less. Build, ship, learn fast.
Humble: Strong opinions, lightly held.
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.)
Our Commitment to an Inclusive Workplace
We welcome people from all backgrounds who seek the opportunity to help build a future where professional services are readily available to all. If you have curiosity, passion, and a collaborative spirit, come work with us. Pearl is committed to an inclusive workplace. Pearl is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, disability, age, or other legally protected status.
AI Disclosure & Informed Consent
Artificial intelligence (AI) technology may be used during the hiring process to record, transcribe, analyze, and rank interview responses. By submitting your application and participating in the interview process, you acknowledge and consent to the use of AI technology in the hiring process. For more information see our AI Disclosure and Consent Policy.

Work arrangement
Yes