Manager, Conversational AI

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, we're redefining how people interact with AI. Conversation Design sits at the center of that transformation, shaping intelligent, intuitive experiences that help millions of customers every day.

As our Manager, Conversational AI, you'll lead a team of talented Conversation Designers while partnering closely with Product, Engineering, Analytics, and AI teams to deliver high-quality conversational experiences at scale.

This role is ideal for a leader who is equally passionate about developing people, building innovative AI experiences, and shaping the future of Conversation Design. You'll help grow exceptional talent, contribute strategic ideas, improve how the team operates, and lead initiatives that strengthen our discipline as AI continues to evolve.

With a builder's mindset, you'll enjoy coaching others, serving as a strategic advisor to cross-functional partners, and rolling up your sleeves to solve meaningful problems. You'll have the autonomy to influence the direction of the organization, own high-impact initiatives, and help define what's next for Conversation Design at Pearl.

What You'll Do

Lead and Develop Your Team

• Lead, coach, and mentor a team of Conversation Designers, helping them grow their skills, deliver exceptional work, and advance their careers.
• Provide regular coaching, performance feedback, career development, and support while fostering a collaborative, high-performing culture.
• Recruit, hire, and onboard future Conversation Designers as the organization continues to grow.
• Remove roadblocks, balance priorities, and empower your team to deliver their best work.

Drive Strategic Impact

• Serve as a strategic thought partner, identifying opportunities to improve conversational experiences and helping shape the future direction of Conversation Design.
• Own a strategic pillar that advances the organization, whether through evaluation frameworks, tooling, workflow improvements, quality practices, or other high-impact initiatives.
• Balance day-to-day execution with long-term thinking to ensure the team continues to evolve alongside customer needs and emerging AI capabilities.
• Bring forward ideas that improve how the team operates and create lasting impact across the organization.

Partner Across the Business

• Collaborate closely with Product Managers, Engineers, Analytics, Machine Learning, and AI teams to deliver exceptional conversational experiences.
• Help teams prioritize work, allocate resources, remove obstacles, and ensure Conversation Designers are set up for success.
• Represent the Conversation Design organization in cross-functional planning, leadership discussions, and strategic initiatives.
• Build trusted partnerships that enable better collaboration and stronger business outcomes.

Build Better Ways of Working

• Bring a builder's mindset by continuously looking for opportunities to improve workflows, streamline operations, and solve problems creatively.
• Use AI and modern tools to enhance productivity, prototype ideas, and explore new ways of working that help the team move faster and smarter.
• Encourage thoughtful experimentation and continuous learning while helping the team stay current with emerging AI capabilities.

What We're Looking For

• Experience leading and developing high-performing teams, ideally within Conversation Design, Conversational AI, or a related discipline.
• Hands-on experience designing and building conversational AI experiences. You're a builder who understands the work because you've done it.
• Experience shipping conversational AI products or AI agents powered by modern LLM technologies.
• Experience improving conversational experiences through evaluation frameworks, optimization, experimentation, A/B testing, or similar quality practices.
• Strong strategic thinking with the ability to anticipate opportunities, connect ideas, and influence direction.
• Experience partnering cross-functionally with Product, Engineering, Data, and AI teams to deliver customer-facing experiences.
• A collaborative leadership style that builds trust, develops talent, and elevates those around you.
• A continuous improvement mindset with a passion for improving workflows, solving problems, and finding smarter ways of working.
• Confidence using AI as part of your daily work and a curiosity for exploring new tools, workflows, and technologies that improve team effectiveness.

Why You'll Love This Role

• Shape the future of Conversation Design. Help define how one of Pearl's fastest-evolving disciplines continues to grow and scale.
• Lead with influence. Own meaningful strategic initiatives while partnering with Product, Engineering, Machine Learning, and AI leaders across the company.
• Stay close to the work. This isn't a management role where you step away from building. You'll continue solving problems, exploring new ideas, and helping shape the future of conversational experiences.
• Build with autonomy. If you see a better way to solve a problem, you'll have the freedom to test it, prototype it, and bring it to life.
• Work in an AI-first environment. We empower our teams with the latest AI tools and encourage experimentation so you can focus on creating impact instead of managing limitations.
• Develop exceptional talent. You'll play a meaningful role in growing the next generation of Conversation Designers while helping define what excellence looks like across the discipline.

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.
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