General Manager

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

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 executive teams 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.
Our Commitment to an Inclusive Workplace

We welcome people from all backgrounds who seek the opportunity to help build a future where professional services are readily available to all. If you have curiosity, passion, and a collaborative spirit, come work with us. Pearl is committed to an inclusive workplace. Pearl is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, disability, age, or other legally protected status.

AI Disclosure & Informed Consent

Artificial intelligence (AI) technology may be used during the hiring process to record, transcribe, analyze, and rank interview responses. By submitting your application and participating in the interview process, you acknowledge and consent to the use of AI technology in the hiring process. For more information see our AI Disclosure and Consent Policy.
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