About the Role

We’re seeking a world-class, market-facing strategist to serve as EVP, Investor Relations & Corporate Development, helping shape the next chapter of Pearl’s journey and fuel a global AI platform that empowers independent professionals to grow, scale, and succeed.

This full-time role is structured as an 18-to-24-month journey, offering the opportunity to lead high-impact work during a key period of strategic growth and operational evolution.

Reporting directly to our CEO, you’ll serve as a business architect and strategic thought partner, shaping company strategy, optimizing our portfolio of brands, and building a compelling blueprint for sustainable, long-term value creation.

This role goes beyond financial discipline. It’s about shaping Pearl’s value story, making the numbers support it, and building confidence with investors, strategic partners, the Board, and other external stakeholders.

You’ll build on an already strong FP&A foundation. This is not an accounting, controllership, or finance reporting role. Your focus will be investor relations, corporate development, strategic finance, long-term value creation, and market-facing leadership alongside the CEO.

You Are:

• A strategic storyteller who sees financials as the language of vision and enterprise value.
• Energized by shaping outcomes, not just reporting them.
• Comfortable engaging directly with investors, analysts, the Board, and strategic partners.
• A proactive, outbound relationship builder who will hustle to expand Pearl’s strategic network and not wait for inbound investor interest.
• A partner to the CEO who thrives in high-velocity, founder-led environments.

You Are Not:

• A traditional CFO, controller, FP&A, or accounting leader focused primarily on budgets, reporting, controls, or month-end discipline.
• Someone primarily motivated by the CFO title or a long-term maintenance role. This is an 18-to-24-month strategic growth journey.

What You’ll Do

• Shape Pearl’s Value Story and Strategic Finance Blueprint: Define and execute a strategy that positions Pearl for long-term value creation, strategic clarity, and compelling external communication.
• Optimize Business Models: Refine our multi-channel strategy (lead generation, B2C, B2B) and develop scalable financial models that highlight future potential and resilience.
• Tell the Strategic Story: Partner with the CEO to communicate our vision and performance with clarity and conviction to investors, the Board, employees, and key external stakeholders.
• Expand Investor and Strategic Networks: Build and nurture relationships with financial, industry, and strategic partners, including investors, analysts, advisors, and ecosystem leaders, to elevate Pearl’s visibility, credibility, and growth opportunities.
• Lead Corporate Development and Strategic Growth: Surface, evaluate, and help execute high-value strategic partnerships, business development opportunities, and growth initiatives that could accelerate enterprise value.
• Unlock Portfolio Value: Evaluate and prioritize growth opportunities across brands, markets, products, and channels to maximize enterprise value.
• Lead a High-Performing Team: Develop and mentor a world-class finance organization focused on insight, impact, execution, corporate development support, and market-facing readiness.
• Drive Strategic Readiness: Ensure financial and operational readiness that supports disciplined planning, scalable growth, and informed decision-making without positioning the role as a traditional CFO search.

What We’re Looking For

• 15+ years of progressive leadership across investor relations, corporate development, strategic finance, investment banking, private equity, top-tier management consulting, or market-facing finance roles; CFO or divisional CFO experience is helpful but not required.
• Proven success shaping company narratives for sophisticated investors, Boards, lenders, analysts, or strategic partners.
• Demonstrated ability to connect financial insight, operating performance, and strategic vision into a persuasive value-creation story.
• Background in corporate development, business development, capital markets, private equity, investment banking, or strategy, with in-house operational exposure strongly preferred.
• Experienced across multi-channel, digital, B2C, B2B, marketplace, or subscription-based business models.
• Strong communicator with boardroom presence, executive gravitas, commercial instincts, and the ability to build confidence externally.
• MBA or advanced degree preferred.

Why You’ll Love It Here

At Pearl, we blend AI innovation and human expertise to make a meaningful global impact. You’ll work directly with a visionary founder and leadership team to shape strategy, scale growth, expand strategic relationships, and define what’s next, all while driving long-term enterprise value in a high-growth environment.

Pay Transparency

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

About the Role

As a Senior Front-end Engineer at Pearl, you will work on customer-facing web applications for international markets and partners. You will join a team responsible for core functionality across international payment flows, post-funnel customer experience, international SEO, and AI-powered features.

You will work closely with Product, UX, and engineering teams to deliver high-quality software solutions, support regulatory and compliance updates for international markets, and contribute to AI-related functionality such as cross-language translation, and automatic PII detection and masking.

You’ll be part of a collaborative team that values ownership, strong engineering practices, continuous improvement, and practical use of AI tools in daily development.

What You’ll Do

• Design, develop, and maintain robust, scalable, and efficient web applications.
• Implement, test, and release new product features for international markets and partners.
• Work on international payment logic, pricing tests and models, Payment Page, post-funnel experience and international SEO initiatives.
• Contribute to AI-powered features, including cross-language translation for customer-expert communication,  and automatic PII detection and masking.
• Collaborate with Product and UX teams to refine requirements and deliver high-quality customer experiences.
• Support regulatory and compliance updates for international markets.
• Ensure high test coverage and follow CI/CD best practices.
• Conduct code reviews and contribute to knowledge sharing across the team.

What We’re Looking For

• 8+ years of professional experience in web development.
• Strong experience with React.js, including state management with Redux and component-based architecture.
• Strong knowledge of front-end technologies such as HTML5, CSS3, JavaScript, TypeScript, Less, React, Redux/Zustand.
• Good understanding of automated testing and willingness to write tests as part of daily development.
• Familiarity with Unit / Integration / Component tests using tools such as Vitest, Playwright, React Testing Library, Jest, or similar.
• Experience with LLMs / Generative AI tools, such as OpenAI, Copilot, Cursor, or similar.
• Experience working in Agile development and ability to handle multiple projects simultaneously.
• Strong understanding of development processes, CI/CD, and engineering best practices.
• Experience with Web Page performance optimization and measurement will be a plus.
• Familiarity with SQL / BigQuery will be a plus.
• Upper-intermediate English proficiency (B2 or higher). 
• Excellent problem-solving and analytical skills, with a keen attention to detail.
• Strong communication and interpersonal skills, with the ability to work effectively in a team-oriented environment.
• Ability to manage multiple tasks and prioritize effectively in a fast-paced environment.

#LI-DNI

About the Role

As an Analyst at Pearl, you will drive tangible business impact by delivering high-quality insights and recommendations that are grounded in your ability to combine strategic thinking and problem-solving with detailed analysis. This position offers a unique opportunity to collaborate closely with Product Managers and cross-functional teams, uncovering valuable business insights, devising optimization strategies, and validating them through experiments. 

What You’ll Do

• Collaborate with Product and Analytics leadership to structure and perform deep-dive analyses, delivering actionable insights into key business areas
• Analyze large datasets (internal and external) to identify growth and optimization opportunities, translating findings into business recommendations and effectively communicating them to stakeholders, including senior leadership
• Perform descriptive and prescriptive analytics using ML models, A/B and MAB experimentation, while building reports to understand business trends 
• Track and implement business metrics to drive continuous improvement and support data-driven decision-making 
• Act as a lead analyst, gaining deep insights into customers to inform strategic decisions

What We’re Looking For

• 3+ years of experience in product analytics (preferably within e-commerce or customer experience products)
• Proficiency in analysis and business modeling using Excel 
• Experience with Google Analytics, BigQuery, PowerBI, and Python / R would be a plus 
• Experience with SQL with a strong ability to write complex queries to extract information and arrive at an answer 
• Expertise in Descriptive Statistical Analysis, Inferential Statistical Analysis 
• Strong experience in setting up and driving A/B Testing or Hypothesis Testing and analyzing the results 
• Ability to translate analysis results into business recommendations, and excellent written and confident verbal communication skills 
• Ability to communicate effectively with all levels of management and partners from a variety of business functions 
• English proficiency (at a strong upper-intermediate level)

The Opportunity

Pearl operates a large consumer marketplace that connects people with independent professionals. We are now building a B2B business to help those professionals acquire clients and grow their own solo practices.

This role is the General Manager of that B2B business. 

You will own the end-to-end strategy, execution, and P&L for our B2B portfolio — building the go-to-market engine that will take the business from early revenue to a $100M+. This role is equal parts strategy and hands-on execution, designed for a leader who thrives in ambiguity. 

What You’ll Own

General Management & P&L

• Full ownership of the B2B business, including P&L, pricing, packaging, and the growth roadmap. 
• Accountability for scaling the business from early revenue to $100M+ over time by building a repeatable go-to-market model and a strong operating foundation.
• Act as CEO of the business line: set priorities, make tradeoffs, and allocate resources for maximum impact

Go-to-Market Strategy & Execution

• Design, build, and scale an end-to-end GTM engine across acquisition, activation, conversion, retention, and monetization, ensuring tight alignment between product, marketing, sales, and customer success.
• Develop and operationalize a repeatable vertical launch playbook, from market selection and positioning through execution, measurement, and iteration.
• Anticipate market and customer inflection points, proactively evolving GTM strategy using leading indicators and pattern recognition—setting direction based on what’s coming next, not just reporting on what’s already happened.
• Translate customer insights and performance data into sustained revenue growth, turning qualitative and quantitative signals into clear priorities, experiments, and scalable growth motions.

Product Operations & Cross-Functional Leadership

• Partner closely with Product, Engineering, Business Development, Operations, and the executive team to identify and launch AI-driven capabilities that materially improve customer outcomes and unit economics.
• Influence product and platform roadmaps to ensure GTM and business economics are tightly integrated.
• Establish operating cadence, KPIs, and governance that enable fast execution without unnecessary bureaucracy.
• Be the “glue” that fosters alignment and connectivity via strong communication, change management, and knowledge management practices down and across team hierarchies.
• Hire and lead the team needed to drive growth as the business scales.

External Leadership

• Represent Pearl externally with partners, at conferences, and within the independent professional ecosystem.
• Build strategic partnerships that accelerate distribution, credibility, and adoption.

What Success Looks Like

First 90 Days

• Deep understanding of the customer, market, product, and revenue mechanics.
• Identification and activation of the highest-impact near-term revenue levers.
• Delivery of a clear GTM roadmap, hiring plan, and initial pricing and packaging hypotheses.

6 Months

• Demonstrable acceleration in acquisition, conversion, and revenue velocity.
• Early proof points that the vertical playbook is repeatable.
• Operating cadence, KPIs, and team structure in place to support scale.

12 Months

• A validated path toward unlocking the broader $100M+ opportunity.
• Pearl positioned as a category-defining platform for independent professionals.

The Ideal Candidate

Required Experience

• GM- or VP-level leader with full P&L ownership.
• Proven experience scaling a B2B, SaaS, marketplace, or platform business from early revenue to tens of millions.
• Deep understanding of SMB, microbusiness, or solo professional markets.
• Hands-on GTM operator with experience building acquisition and conversion engines.
• Comfortable operating in zero-to-one and one-to-many environments with incomplete playbooks.

Strongly Aligned Backgrounds

• Experience at companies serving independent professionals or small businesses (e.g., Intuit, Shopify, Square, Toast, GoDaddy, or similar).
• Experience launching new verticals or business lines from scratch.
• Experience building or commercializing AI-powered products.

Leadership Profile

• Entrepreneurial, high-ownership mindset with a bias for action.
• Comfortable with ambiguity and capable of bringing clarity quickly.
• Data-driven, customer-obsessed, and outcomes-oriented.
• Willing to operate at both strategic and executional levels.

Nice to Have

• Marketplace, lead-generation, or freemium business model experience.
• Experience in legal tech or related vertical SaaS markets serving independent professionals.
• Founder experience with strong learning velocity.
• Experience leading businesses as GM, Head of B2B, VP GTM, or similar.

Why Join Pearl

• True ownership: a GM role with real authority and accountability.
• A massive market opportunity at the intersection of AI and independent professionals.
• Ability to shape product, GTM, and team from the ground up.
• Backed by an established consumer platform.
• A rare opportunity to build a category-defining business, not just optimize an existing one.

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.)

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

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.)

About the Role

As an Analyst, Digital Marketing, you will manage and optimize Google Ads campaigns, analyze performance data, and collaborate with cross-functional teams to drive better ROAS/CPA while maintaining robust tracking and reporting practices.

What You’ll Do

• Build and optimize Google Ads campaigns, including structure, keyword research, targeting, and ad creatives.
• Conduct experiments, analyze segmented performance data, and drive improvements in CTR, conversion rate, ROAS, and CPA.
• Monitor daily metrics, identify anomalies, and address performance or tracking issues proactively.
• Use Excel and SQL to analyze large datasets and support bid/budget optimization decisions.
• Collaborate with Analytics, Product, Engineering, and market teams while ensuring strong tracking, tagging, and measurement hygiene (UTMs, GA4, conversion tracking).

What We’re Looking For 

• 5–8 years of experience in performance/search marketing, including 3+ years managing Google Ads campaigns end-to-end.
• Strong knowledge of Google Ads fundamentals, bidding strategies, auction dynamics, quality score, and search query analysis.
• Data-driven mindset with the ability to define KPIs, analyze trends, and make evidence-based recommendations.
• Advanced Excel/Sheets skills and working knowledge of SQL for handling large datasets.
• Familiarity with GA/GA4, conversion tracking, and attribution basics.
• Clear communicator, comfortable sharing insights with cross-functional teams.
• Flexible to attend planned evening IST meetings to overlap with US teams.
• Leverages AI for creatives, keyword clustering, anomaly detection, real-time insights, and automated reporting to enhance strategy and efficiency.

Good to have

• Google Ads Search certified or equivalent practical experience.
• Exposure to Microsoft Ads, Display/YouTube, or other paid channels.
• Experience with dashboarding tools (Looker Studio, Power BI, Tableau) and/or basic scripting (Python).
• Familiar with A/B testing, experimentation frameworks, and statistical fundamentals.
• Comfortable using LLM/prompting tools to enhance analysis and reporting productivity (as per policy).

About the Role

 As Analyst, International Operations, you’ll turn raw HR data into real business impact, shape predictive insights for leaders, and help architect the future of workforce intelligence at our company. 

What You’ll Do

• Build predictive models for workforce planning, retention, hiring, and compensation—shifting us from reporting to proactive, forward-looking insights. 
• Integrate data from different data hubs (HRIS, ATS etc.) to create real-time dashboards in Power BI. 
• Automate and maintain agentic AI across People Ops to accelerate decision-making. 
• Own the accuracy of People Insights dashboards—monitor refresh cycles, troubleshoot issues, and ensure top-quality predictive outputs. 
• Build and enhance Power BI dashboards, SQL queries, and data models to support new programs and analytics needs. 
• Use AI tools (Power BI Copilot, AutoML, ChatGPT) to streamline data prep, generate insights, and scale predictive analytics. 
• Partner with stakeholders to gather requirements and continually evolve metrics, dashboards, and AI-driven features. 

What We’re Looking For

• 1.5+ years of experience in analytics or HR operations.
• Proficiency with analytical tools and systems such as Power BI, SQL (basic), Python (basic) and Excel (including macros).
• Experience with predictive analytics, modeling, or forecasting.
• Experience working with project management tools like Microsoft Project, Asana, or similar platforms.
• Strong stakeholder management skills and experience gathering, clarifying, and prioritizing requirements.
• At least upper-intermediate English level.
• Strong attention to detail, analytical thinking, and problem-solving abilities.

About the Role

As a Senior Manager, Analytics at Pearl, you’ll be part of a mission-driven team that is transforming professional services through AI + human expertise. Our Analytics team is at the heart of this mission, building insights and frameworks that guide smarter decisions, fuel innovation, and transform how people connect with expertise.

In this role, you’ll lead a team of talented analysts who work across multiple strategic initiatives—from funnel optimization and customer quality to AI-driven experimentation. You’ll shape how we collect, interpret, and act on data across the business, developing both the technical infrastructure and the analytical culture that enables Pearl to move faster and think smarter.

This is a role for someone who loves data and people in equal measure—someone excited to roll up their sleeves with SQL and Python one moment, and coach their team or present insights to executives the next. You’ll bring a balance of strategic vision, hands-on technical skill, and mentorship to help your team—and the company—reach the next level of data maturity.

What You’ll Do

• Lead & Grow a High-Impact Team: Manage and develop a team of analysts (approx. 6), helping them level up their skills, expand their impact, and grow in their careers.
• Be a Strategic Partner: Collaborate with leaders across the business to shape experiments, define success metrics, and translate data into action.
• Stay Hands-On: Dive deep into data when needed — writing SQL queries, Python scripts, and building Power BI dashboards. Lead by example and set the standard for analytical excellence.
• Champion AI & Innovation: Leverage AI tools and APIs (e.g., ChatGPT, Gemini) to automate insights, explore unstructured data, and modernize the way we do analytics.
• Share the Story: Lead analytics reviews and present findings to cross-functional and executive audiences — turning data into clear, compelling narratives.
• Collaborate Cross-Functionally: Work closely with Data and Engineering teams to ensure data accuracy, experimentation design, and analytics scalability.

What We’re Looking For

• 5–10 years of experience in analytics, data science, or a related field (We’re open to exceptional candidates with slightly less experience who demonstrate strong leadership and deep AI/experimentation expertise.)
• Strong technical skills: SQL, Python, and data visualization tools (Power BI preferred)
• Proven experience designing and analyzing experiments (A/B testing, Bayesian, or multi-armed bandit approaches)
• Experience working with APIs and modern AI tools
• Demonstrated success as a people leader — coaching, mentoring, and developing analysts
• Excellent communication and storytelling skills — able to explain complex data clearly to any audience
• A growth mindset and a passion for applying AI in analytics
• Location: This role is remote, with a strong preference for candidates located on the U.S. East Coast to support collaboration across time zones.

What Sets Top Candidates Apart

The strongest candidates will bring experience in one or more of the following areas:

• Marketplace analytics: Experience analyzing and optimizing two-sided marketplaces where supply and demand dynamics influence product performance and user outcomes.
• B2C and B2B ecosystems: Experience analyzing products and user behavior in both consumer-facing (B2C) and business-facing (B2B) environments, with an understanding of the different metrics, growth levers, and customer journeys in each.
• Agentic AI: Experience working with or analyzing AI agent workflows, conversational systems, or AI-assisted product features.
• Subscription-based business models: Familiarity with metrics and experimentation related to subscription acquisition, retention, churn, and lifetime value.

What to Expect in Your First 90 Days

• First 30 days: Learn our data, tools, and people. Understand how analytics drives our initiatives.
• By 60 days: Shape team development plans, clarify goals, and start leading key deliverables.
• By 90 days: Deliver your first analytics business review and showcase insights to leadership.

Why You’ll Love It Here

At Pearl you’ll work with billions of real user interactions — an unparalleled data set for experimentation and insight. You’ll collaborate with a team that’s pushing analytics beyond traditional dashboards and A/B tests, pioneering new methods like multi-armed bandits and Bayesian experimentation.

We’re transforming analytics with AI — and we’re doing it at scale. If you want to lead a team where curiosity, innovation, and data drive everything we do, this is the job for 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.)

Pearl, the parent company of JustAnswer, is building a category-defining enterprise business at the intersection of AI and professional human expertise. We believe the next wave of AI progress will come from models that do work, not just answer questions. That requires higher-quality training and evaluation data built by real experts.

Pearl is uniquely positioned to win in this space. We have a network of more than 20,000 licensed professionals, two decades of experience operating high-trust expert workflows, and multimodal capabilities across chat, voice, and computer-use tasks.

The opportunity

We are looking for a leader to build Pearl’s AI data business into a trusted partner for frontier AI labs and AI-native companies. This role will define what we sell, how we deliver it, and how we ensure quality at scale.

This is not a quota-carrying sales role. It is a product and operations leadership role with deep customer intimacy. You will work across discovery, solution design, delivery, quality, and expansion to turn complex AI research needs into repeatable expert data programs.

What you will own

• You will define and productize Pearl’s AI data offerings, including how they are packaged, delivered, measured, and improved over time.
• You will build the delivery engine for expert data programs across staffing, workflows, tooling, QA, and automation.
• You will establish the quality bar through rubrics, audits, calibration, gold sets, verifiers, and continuous performance scoring.
• You will partner closely with customers to translate ambiguous training and evaluation needs into clear task designs, workflows, and production-ready specifications.
• You will help shape Pearl’s data rights and licensing strategy with Legal so we can scale responsibly while protecting confidentiality, privacy, and customer trust.
• You will also help build Pearl’s credibility in the market by defining clear standards for what elite expert data looks like.

Examples of programs you may build

• Expert training data for specialized domains
• Preference and ranking data with strong rubrics
• Evaluation programs for truthfulness, reasoning, safety, and policy adherence
• Verifier, critique, and structured feedback workflows
• Hard-case and adversarial datasets that expose model failure modes
• Agentic and long-horizon tasks involving tools, software, and decision-making
• Multimodal programs across text, voice, and computer-use environments

What we are looking for

• You have experience in AI data services, AI data product leadership, ML research operations, AI partnerships, or a related field.
• You have built or operated high-quality human data programs such as supervised fine tuning, preference data, evaluations, verifiers, critiques, or rubric-driven QA.
• You are comfortable working with ML researchers, engineers, and technical product teams on dataset design, formats, and evaluation methodology.
• You know how to turn ambiguous customer or research needs into structured workflows and production-ready delivery plans.
• You have strong operational judgment and understand what it takes to build quality, trust, and repeatability in a fast-moving environment.
• Experience with data rights, licensing, confidentiality, or enterprise-grade data delivery is strongly preferred.

Ideal backgrounds may include

• AI data procurement or partnerships at a frontier AI lab or model-building organization
• Senior leadership at a custom AI data provider such as Scale, Appen, Prolific, or a similar company
• Data product or research operations leadership in an AI-native environment

Why this role matters

A strong leader in this role could unlock a significant new business for Pearl by helping us deliver expert training and evaluation data to leading AI labs. This is an opportunity to build something important from the ground up and define a category where Pearl has a real right to win.

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.

About the Role

As a Bilingual Customer Service Representative at Pearl, you will serve as the frontline connection to our customers, providing exceptional support and ensuring their needs are met efficiently and professionally. You will be responsible for handling customer interactions in German, resolving issues, and delivering a seamless customer experience. If you are customer-centric, detail-oriented, and passionate about delivering quality service, this role is for you.

What You’ll Do

• Respond to customer inquiries and issues via voice and/or non-voice transactions while demonstrating attentive listening and effective communication.
• Identify and assess customer needs through active listening and questioning, providing timely and accurate resolutions in line with company guidelines.
• Maintain detailed and accurate records of customer interactions, including actions taken and resolutions provided.
• Update and manage customer accounts and profiles to ensure accurate, up-to-date information for efficient service delivery.
• Acquire in-depth knowledge of company products, processes, and policies to provide accurate information and resolve issues effectively.
• Continuously enhance product knowledge and customer service skills through training and learning opportunities.
• Collaborate with team members and other departments to ensure seamless customer experiences and prompt issue resolution.
• Meet or exceed performance metrics, including quality scores, customer satisfaction ratings, and schedule adherence.

What We’re Looking For

• Ability to work during German business hours
• C1-C2 level or native proficiency in German; at least B2 English level.
• At least 6 months of professional customer support experience in the German language.
• Strong customer support, multitasking, and communication skills.
• Preferred experience in phone and email-based customer support.
• Fast and accurate typing skills.
• Self-motivation and basic computer knowledge.
• Familiarity with customer-support-relevant AI usage language

Why You’ll Love Working With Us

• Make a Real Impact: Be part of a dynamic team that values inclusivity, creativity, and continuous improvement.
• Empower Communities: Play a key role in fostering meaningful interactions and creating resources that genuinely help users.
• Collaborative Environment: Partner with cross-functional teams who value your expertise and insights.
• Grow Your Skills: Enhance your customer service expertise, develop effective communication techniques, and learn to resolve complex issues while contributing to a high-quality customer experience.
• Remote Flexibility and Work-Life Balance: Enjoy a great work-life balance while working remotely. Collaborate with a global team, and thrive in a culture that prioritizes well-being, personal development, and work-life balance.

About the Role

As a Full Stack Developer, you will play a pivotal role in designing, developing, and maintaining our web applications, ensuring high performance and scalability. You will work closely with cross-functional teams to deliver high-quality software solutions while contributing to projects that integrate advanced machine learning models, including large language models (LLMs), to deliver personalized user experiences and innovative features. You'll be part of a small, collaborative team that values continuous improvement and embraces the latest in technology.
 
Our technology stack includes .NET Core, C#, React.js, Node.js, Typescript, SQL Server 2019, Docker, Kubernetes, Google Analytics, and Power BI.  

Our ecosystem includes 170 connected applications and services, our main database is 2 TB, our sites handle 1 million visitors a day and 2 billion requests a month, and we release changes to production several times a day. We are a continuous integration and continuous deployment (CI/CD) organization. 

What You’ll Do

• Collaborating with cross-functional teams to demonstrate how they can effectively leverage our infrastructure to meet their objectives. 
• Designing, developing, and maintaining robust, scalable, and efficient web applications, backend logic modules and database structure.
• Identifying and implementing strategies to improve the stability, performance, and scalability of our applications and services. 
• Responding promptly to production incidents, employing creative problem-solving skills to minimize downtime and mitigate potential issues. 
• Supporting team members, fostering a culture of continuous learning and technical excellence. 
• Conducting code reviews and ensuring adherence to coding standards and best practices across the team. 
• Participating in the evaluation and integration of new technologies, including AI and automation tools, to drive innovation and efficiency. 

What We’re Looking For

• Minimum of 3 years of professional experience in full stack development.
• Extensive experience with React.js, including state management (Redux, Context API) and component-based architecture.
• Proficiency in .NET frameworks, C#, and data access technologies.
• Familiarity with Unit / Integration tests using any of Jest, NUnit, Playwright, React Testing Library.
• Strong knowledge of front-end technologies such as HTML5, CSS3, JavaScript, and TypeScript.
• Familiarity with database systems such as SQL Server or MySQL.
• Strong knowledge of design and architectural patterns, SOA design & web service development.
• Strong understanding of development processes.
• Experience with LLMs / Generative AI tools (e.g., OpenAI, Copilot, Cursor).
• Experience with Web Page performance optimization and measurement will be a plus.
• Degree in Computer Science, a related discipline or equivalent work experience.
• Upper-intermediate level of English.
• Excellent problem-solving and analytical skills, with a keen attention to detail.
• Strong communication and interpersonal skills, with the ability to work effectively in a team-oriented environment.
• Ability to manage multiple tasks and prioritize effectively in a fast-paced environment.

About the Role

As a Lead Software Engineer in our Machine Learning department, you will take ownership of high-impact initiatives that drive product quality, monetization, and user experience. You’ll apply your expertise in Python, data analysis, and modern AI tools to build, deploy, and optimize ML solutions end-to-end. This is a hands-on technical role that blends data science and engineering to deliver measurable business outcomes. You’ll collaborate closely with cross-functional stakeholders and contribute to evolving areas such as LLMs, Generative AI, and ML infrastructure. The role offers exposure to complex data challenges and the opportunity to shape Pearl’s AI-driven capabilities.

What You’ll Do

• Build, train, and deploy ML models that improve product performance and monetization.
• Collaborate with data, product, and engineering teams across multiple internal initiatives.
• Design and implement data pipelines for extraction, transformation, and analysis.
• Apply statistical and machine learning techniques to real-world business problems.
• Work on projects involving LLMs and Generative AI technologies.
• Analyze large datasets to identify trends, insights, and optimization opportunities.
• Integrate ML models into production systems and monitor their performance.
• Communicate findings and recommendations clearly to technical and non-technical stakeholders.
• Experiment with emerging AI tools and methodologies to enhance existing workflows.
• Ensure data quality, reliability, and scalability in all deliverables.

What We’re Looking For

• 3+ years of hands-on experience in ML Engineering or Data Science.
• 5-6+ years total experience in software or data engineering.
• Strong programming skills in Python.
• Proficiency in SQL for data querying and analysis.
• Solid understanding of data processing, analysis, and visualization.
• Experience with LLMs / Generative AI tools (e.g., OpenAI, Copilot, Cursor).
• Ability to build and deploy ML models end-to-end.
• Strong analytical and problem-solving mindset.
• Experience with .NET for integration work 
• Upper-intermediate English proficiency (B2 or higher). 
• Familiarity with Databricks or similar data platforms (nice-to-have).
• Exposure to AWS or other cloud-based ML environments (nice-to-have).

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.

About the Role

We’re hiring a Marketing & Community Manager based in the San Francisco Bay Area to help Pearl show up where the AI world actually happens.

This isn’t traditional marketing. It sits at the intersection of community, partnerships, and field marketing, with a strong bias toward action. You’ll build relationships with founders, engineers, and operators at leading AI companies—and shape how Pearl is perceived across the ecosystem.

If you’re already in the room—or know how to get in—you’ll thrive here.

What You’ll Do

Build Pearl’s Presence in the AI Ecosystem

• Engage deeply on platforms like X, Reddit, and other AI-native communities
• Contribute meaningfully to conversations—bringing insight, not noise
• Help define and evolve Pearl’s voice across social and community channels

Show Up in the Field

• Attend AI events across the Bay Area (meetups, dinners, conferences)
• Represent Pearl on the ground and build high-value relationships
• Execute event strategy—from scrappy activations to major conference moments

Drive Partnerships & Strategic Relationships

• Identify and connect with top AI companies and ecosystem players
• Initiate and support partnership conversations
• Turn relationships into tangible opportunities in collaboration with internal teams

Create Content That Resonates

• Develop or collaborate on sharp, relevant content (social, thought pieces, outreach)
• Translate complex AI capabilities into clear, compelling narratives
• Tailor messaging for both technical and non-technical audiences

Collaborate Across Teams

• Partner with enterprise, product, and leadership on GTM and positioning
• Bring back insights from the field to inform product and strategy

What Success Looks Like

• Pearl is visible, credible, and respected in key AI communities
• You’ve built strong relationships with high-value partners and operators
• Conversations you start convert into real opportunities
• You consistently identify opportunities—and act on them quickly

Who You Are

Deeply plugged into AI: You follow the space closely and can hold your own in conversations. You don’t need to be highly technical, but you understand the landscape and ask sharp questions.

A natural connector: You’re energized by meeting people and building relationships. You’re credible, curious, and know how to create momentum from a conversation.

Location: Based in the San Francisco Bay Area and willing to attend multiple in-person events per month

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

About the Role

As a Senior Analyst at Pearl, you will be a Subject Matter Expert (SME) in professional services domain, driving long-term growth and leveraging the latest technologies and methodologies.
 
In this role, you will drive tangible business impact by delivering high-quality insights and recommendations that are grounded in your ability to combine strategic thinking and problem-solving with detailed analysis. This position offers a unique opportunity to collaborate closely with Product Managers and cross-functional teams, uncovering valuable business insights, devising optimization strategies, and validating them through experiments. 

What You’ll Do

• Collaborate with Product and Analytics leadership to conceive and structure analysis and deliver highly actionable insights from “deep dives” into specific areas of our business.
• Conduct analysis of a tremendous amount of internal & external data to find growth & optimization opportunities for the business.
• Package and communicate findings and recommendations to a broad audience (including senior leadership).
• Perform both Descriptive & Prescriptive Analytics including experimentations (AB, MAB), build Reporting for understanding trends.
• Implement and track business metrics that will help drive the business.
• Help determine growth strategy from a marketing and operations perspective.
• Opportunity to operate in an individual capacity as a lead analyst to understand the customer and guide informed strategic decisions & executions.  

What We’re Looking For

• 7+ years of experience in e-commerce/customer experience products
• Proficiency in analysis and business modeling using Excel
• Experience with Google Analytics, BigQuery, PowerBI, and Python / R would be a plus
• Experience with SQL with a strong ability to write complex queries to extract information and arrive at an answer
• Expertise in Descriptive Statistical Analysis, Inferential Statistical Analysis
• Strong experience in setting up and driving A/B Testing or Hypothesis Testing and analyzing the results
• Ability to translate analysis results into business recommendations, and excellent written and confident verbal communication skills
• Ability to communicate effectively with all levels of management and partners from a variety of business functions
• Advanced English level

About the Role 

As an Analyst at Pearl, you will drive tangible business impact by delivering high-quality insights and recommendations that are grounded in your ability to combine strategic thinking and problem-solving with detailed analysis. This position offers a unique opportunity to collaborate closely with Product Managers and cross-functional teams, uncovering valuable business insights, devising optimization strategies, and validating them through experiments. 

What You’ll Do

• Collaborate with Product and Analytics leadership to conceive and structure analysis and deliver highly actionable insights from “deep dives” into specific areas of our business
• Conduct analysis of a tremendous amount of internal & external data to find growth & optimization opportunities for the business 
• Package and communicate findings and recommendations to a broad audience (including senior leadership)  
• Perform both Descriptive & Prescriptive Analytics including experimentations (AB, MAB), build Reporting for understanding trends 
• Implement and track business metrics that will help drive the business
• Help determine growth strategy from a marketing and operations perspective 
• Opportunity to operate in an individual capacity as a lead analyst to understand the customer and guide informed strategic decisions & executions

What We’re Looking For

• 5 years of experience in e-commerce/customer experience products
• Proficiency in analysis and business modeling using Excel 
• Experience with Google Analytics, BigQuery, PowerBI, and Python / R 
• Experience with SQL with a strong ability to write complex queries to extract information and arrive at an answer 
• Expertise in Descriptive Statistical Analysis, Inferential Statistical Analysis 
• Strong experience in setting up and driving A/B Testing or Hypothesis Testing and analyzing the results 
• Ability to translate analysis results into business recommendations, and excellent written and confident verbal communication skills 
• Ability to communicate effectively with all levels of management and partners from a variety of business functions 
• Advanced English level 

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

About the Role

We’re looking for an iOS engineer who loves building high-performance, scalable apps and knows Swift inside and out. You’ll design and ship polished UI/UX, own end-to-end delivery, and collaborate across product, Android, backend, and analytics to drive impact.

What You’ll Do

• Build, debug, and ship high-quality iOS features and apps end-to-end.
• Implement modern iOS UI with UIKit and SwiftUI, including animations, transitions, CALayer/CAAnimation.
• Apply and advocate for solid architectures (MVP, MVVM, VIPER), choosing the right approach for the job.
• Drive quality with automated tests (unit, integration, E2E) and CI/CD pipelines.
• Own multi-environment builds, config injection, and App Store releases.
• Implement push notifications, deep linking, and platform best practices.
• Boost development speed and quality using AI for coding, refactoring, debugging, test generation, and automating repetitive tasks.
• Strengthen collaboration and innovation with AI-driven requirement summaries, Android–iOS logic translation, and insights that enhance UX, analytics, and performance.
• Translate product UX mocks into performant, maintainable code; estimate and propose pragmatic solutions.
• Collaborate with Android to ensure feature parity and translate Android/Kotlin logic to iOS where needed.
• Participate in code reviews, mentor teammates, and improve engineering processes and tooling.
• Contribute to analytics and A/B testing in high-traffic production environments.

What We’re Looking For

• 3+ years of professional iOS development in Swift language.
• Deep knowledge of UIKit, SwiftUI, iOS UI architecture, animations, and performance tuning.
• Strong grasp of MVP/MVVM/VIPER and their tradeoffs.
• Proven experience with App Store releases, multi-environment builds, and config injection.
• Solid understanding of push notifications, deep linking, and modern iOS capabilities.
• Experience with automated testing across layers and CI/CD for iOS.
• Ability to solve algorithmic problems and analyze data to inform decisions.
• Experience with cross-functional teams, high-traffic apps, analytics, and A/B testing.
• Clear communicator who thrives in fast-paced, ambiguous environments; champion of TDD and code quality.
• Familiarity with full-stack concepts; experience mentoring; Android/Kotlin literacy.

Why You’ll Love It Here

At Pearl, you’ll build a high-impact iOS app used by millions, applying modern architecture, Swift expertise, and rigorous experimentation in a culture of continuous delivery and deep cross-functional collaboration.
You’ll harness AI to ship faster—auto-generate code/tests/docs, improve code reviews and CI/CD, translate Android↔iOS logic, and surface insights that elevate UX and performance.