About the Role

As an Analyst at Pearl, you will drive tangible business impact by delivering high-quality insights and recommendations grounded in your ability to combine strategic thinking with rigorous analysis. This role requires not only strong technical skills, but also the confidence and judgment to proactively identify opportunities, challenge assumptions, and advocate for data-informed decisions.

You will collaborate closely with Product Managers, executives, and cross-functional teams to uncover insights, shape strategy, and validate ideas through experimentation.

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 clear, compelling business recommendations
• Proactively surface insights and confidently make recommendations, even in ambiguous or evolving problem spaces
• Partner cross-functionally with Product, Engineering, Marketing, and executive stakeholders to align on priorities and drive outcomes
• 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 is a plus
• Strong SQL skills with the ability to write complex queries to extract insights
• Expertise in descriptive and inferential statistical analysis
• Strong experience designing, executing, and analyzing A/B or hypothesis-driven experiments

Core Soft Skills & Ways of Working:

• Confident decision influencer: Comfortable making recommendations and advocating for a point of view backed by data—even when there isn’t a perfect answer
• Executive communication: Ability to clearly and concisely communicate insights, trade-offs, and recommendations to senior leadership
• Cross-functional collaborator: Proven ability to partner effectively with diverse teams and navigate differing priorities
• Curiosity and ownership: Proactively identifies problems and opportunities without waiting for direction
• Comfort with ambiguity: Able to operate in loosely defined problem spaces and bring structure to complex questions
• Storytelling with data: Translates complex analysis into clear, compelling narratives that drive action

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

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.)

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 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

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.)