Pearl
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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: Data decides, not egos
- Courageous: We take risks and challenge the status quo
- Innovative: We're constantly learning, creating, and adapting
- Lean: We focus on customers, using lean testing to learn how to serve them best
- Humble: Past success is not a guarantee of future success
About the Role
As a Conversation Designer at Pearl, you’ll help build and evolve chatbots that support and convert millions of customers around the world. You’ll design engaging, efficient conversational flows using our in-house language, blending creativity with data to deliver delightful AI + Human-powered experiences. This role requires technical proficiency, cross-functional collaboration, and a passion for building user-centric solutions that move business metrics.
What You’ll Do
- Design and optimize chatbot flows to convert, engage, and support customers across e-commerce and customer service journeys
- Write clear, compelling conversation copy that aligns with brand tone and business objectives
- Analyze customer transcripts and chatbot performance to identify gaps and propose improvements
- Apply NLP/LLM tools and prompt engineering to enhance response quality and scalability
- Partner with international teams to localize and align bots with regional goals and personas
- Collaborate with analytics to evaluate performance metrics and measure impact
- Conduct QA (functional, linguistic, and regression) testing of bot interactions
- Lead or contribute to special projects (e.g., chatbot consolidation, competitor analysis, new bot launches)
What We’re Looking For
- 2+ years of experience designing, launching, and maintaining chatbot or conversational AI solutions
- Familiarity with NLP platforms like Dialogflow, Watson, or similar
- Experience with LLMs and prompt engineering
- Working knowledge of Python, HTML, or JavaScript
- Strong data fluency and comfort with tools for analyzing performance at scale (Excel, PowerBI, etc.)
- Comfortable working in Agile environments and using tools like Asana, Azure Boards, Figma, or LucidChart
- Excellent attention to detail, organization, and project management skills
- Thrives in fast-paced, collaborative, and iterative environments
- Experience with ChatScript or other chatbot scripting languages
- Experience localizing chatbots for global audiences
- Prior work in marketplaces, e-commerce, or customer experience teams
- Ability to independently lead QA testing and post-launch analysis
Why Join Pearl
- At Pearl, we’re redefining how people access expert help—combining AI-powered conversation design with human expertise to deliver fast, personalized support.
- You’ll join a global, mission-driven team working at the intersection of technology, language, and empathy. Every interaction you design helps someone get answers, make decisions, or solve a problem that matters.
- We offer a flexible, collaborative environment where designers, engineers, and product thinkers shape the future of AI + Human interaction together.
The Impact You’ll Have
- Your work will directly influence how millions of customers experience Pearl every month—turning complex questions into simple, conversational solutions. You’ll help us scale intelligent, empathetic digital experiences that feel less like tech—and more like help.
- This is your opportunity to shape the future of AI-human interaction in a company that’s redefining expert access at scale. If you’re passionate about designing conversations that matter—and you like solving tough problems with smart people—we’d love to hear from you.
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.
#LI-Remote
Ready to apply?
Apply to Pearl
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: Data decides, not egos
- Courageous: We take risks and challenge the status quo
- Innovative: We're constantly learning, creating, and adapting
- Lean: We focus on customers, using lean testing to learn how to serve them best
- Humble: Past success is not a guarantee of future success
About the Role
As a Senior Product Manager at Pearl, you will own discovery, strategy, and execution for high-impact products supporting Pearl Enterprise, with direct responsibility for driving revenue outcomes (including Enterprise contracts totaling $2.5M+). This is a hands-on, high-ownership PM role in a fast-moving, ambiguous environment. You will partner closely with Engineering, AI / Innovation (IL), Sales, and cross-functional stakeholders to define priorities, set OKRs, and deliver results at Pearl-speed. Pearl’s product itself is increasingly AI-driven, and while this role does not require you to be an AI engineer, it does require comfort working with AI-powered products, AI prototypes, and AI-enabled teams.
What You’ll Do
Product Ownership & Execution
- Own the end-to-end discovery PM role: problem definition, prioritization, roadmap creation, execution, and delivery.
- Partner with IL / AI leaders to define OKRs, priorities, and quarterly roadmaps aligned to Enterprise goals.
- Lead agile teams to execute against the roadmap with speed, focus, and accountability.
- Own releases and delivery using lean and agile practices, balancing experimentation with execution.
Discovery, Data & Decision-Making
- Drive discovery through customer research, data analysis, experimentation, and rapid validation.
- Define product requirements for MVPs, AI-enabled features, and enhancements.
- Use product metrics and insights to inform decisions, measure impact, and iterate quickly.
- Operate with a strong data-driven mindset, making clear, timely decisions in ambiguous situations.
Cross-Functional Collaboration
- Partner closely with B2B sales, Enterprise stakeholders, customers, and partners to identify market problems and opportunities.
- Act as a strong cross-functional collaborator, aligning Engineering, AI, Sales, and Leadership.
- Clearly communicate the “why,” connect work to outcomes, and ensure focus on the highest-leverage initiatives.
What We’re Looking For
Experience & Skills
- 5+ years of Product Management experience in B2B web or platform products.
- Proven experience delivering first-generation or early-stage products.
- Comfort working with AI-powered products; experience with GenAI is a strong plus.
- Bonus: Ability to build or collaborate on AI prototypes to accelerate discovery.
- Strong experience with experimentation, MVP definition, and iterative delivery.
Core Traits & Capabilities
- Adaptability – Proven success operating in volatile, uncertain, complex, and ambiguous (VUCA) environments.
- Efficiency & Pace of Execution – Demonstrated ability to deliver results quickly using standard PM and lean start-up practices (“Pearl-speed”).
- Collaboration – Strong track record partnering cross-functionally, especially with B2B sales and Enterprise stakeholders.
- High Ownership Mindset – Proactive, accountable, and comfortable operating with minimal oversight.
- Data-Driven Decision Making – Uses data, not opinion, to guide priorities and trade-offs.
- Quick, Confident Decision-Making – Able to make informed decisions with imperfect information.
- Dependability – High follow-through and reliability on commitments.
- Strategic Thinking – Sees the big picture, communicates it clearly, and ensures work maximizes impact against OKRs.
- Growth Mindset – Open to feedback, continuously improving, and eager to learn.
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.
#LI-Remote
Ready to apply?
Apply to Pearl
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: Data decides, not egos
- Courageous: We take risks and challenge the status quo
- Innovative: We're constantly learning, creating, and adapting
- Lean: We focus on customers, using lean testing to learn how to serve them best
- Humble: Past success is not a guarantee of future success
About the Role
We are seeking an AI Prompt Engineer II who combines strategic thinking, scientific expertise, and hands-on building skills. You will join a dynamic, agile team dedicated to designing, testing, and scaling large language model (LLM) prompts that drive impactful user experiences. Leveraging your deep knowledge of Generative AI, you will enhance our AI-powered expert platform, unlocking meaningful business outcomes and shaping how AI understands customers and supports experts.
What You’ll Do
- Design, build, and develop AI agents
- Create complex multi-part prompting systems with parameter optimization and implement advanced prompting techniques
- Develop comprehensive evaluation frameworks to measure performance across multiple dimensions, comparing approaches such as retrieval-augmented generation (RAG), fine-tuning, and advanced prompting methodologies
- Analyze and optimize LLM performance using A/B testing, usage metrics, and strategic feedback loops
- Develop AI-driven workflows that improve user interactions and Customer Care support
- Design and refine expert playbooks to enhance knowledge sharing and operational efficiency
- Run experiments to validate ideas rapidly and iterate based on performance data and user insights
- Collaborate cross-functionally with product managers, engineers, and stakeholders to identify LLM opportunities and translate technical capabilities into business value
- Manage stakeholder expectations and communicate complex technical concepts effectively to both technical and non-technical audiences
- Implement LLMOps best practices including model governance, lifecycle management, and performance monitoring to ensure production-ready AI systems
- Educate and empower internal teams to build better prompts and leverage AI tools effectively
What We’re Looking For
- Master’s or PhD in Computer Science, Computational Linguistics, Machine Learning, or a related field preferred
- Strong proficiency in Python with hands-on experience building and testing complex prompting systems
- Deep understanding of LLMs and advanced frameworks, with expertise across multiple LLM vendors and model versions
- Proven experience developing and applying evaluation frameworks to test model outputs
- Production experience with RAG and fine-tuning models
- Demonstrated ability to automate large-scale API interactions and scripting for prompt testing, minimizing manual processes
- Experience with LLMOps practices, including model governance, version control, performance monitoring, and lifecycle management
- Strong stakeholder management skills and ability to collaborate effectively across technical and business teams
- Proven track record of translating complex technical concepts into actionable business insights for diverse audiences
- Analytical mindset with experience using Excel, Power BI, or Google Analytics
- Solid understanding of NLP techniques
- Excellent judgment with the ability to prioritize and independently drive projects forward while managing multiple stakeholder relationships
- Experience working in agile, sprint-based development environments; familiarity with tools such as Azure Boards or Asana
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.
#LI-Remote
Ready to apply?
Apply to Pearl