VP & General Manager, B2B

Pearl

2d•Remote

About The Position

Pearl is AI for professional services at global scale—combining advanced AI with verified human expertise to deliver help that’s 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 is a successful B2C company. Inside, we are building a fast-growing B2B business focused on independent professionals (We call it B2P). We want a VP to run this division like a CEO and scale it from early revenue to $100M+. Your mandate is simple. Build the category-defining growth engine for independent professionals. Lead GTM and P&L. Use our expert network, customer leads/relationships, AI assets, team and data to win the independent professional market starting with solo lawyers. The focus is on strategy and bold execution, not incrementalism. What You Own This role is central to the launch and growth of Pearl.com, our new platform for independent professionals and the home for all of our professional-facing offerings—including Fount and future AI-driven services. You will lead our entire B2B portfolio with a primary focus on Fount, our AI-powered client acquisition and business platform for solo professionals. Fount is not a CRM. It is a client acquisition machine for independent lawyers and other pros. The product is built around delivering paying clients to solo professionals. The GTM model is freemium, with paid leads, payment processing and other AI+Human services as the monetization. The Mission Scale revenue to $100M+. Prove and scale the Fount playbook for independent professionals. Build a repeatable vertical launch engine (legal first, then others). Drive high-velocity AI innovation to deliver a 10X value proposition. Build the GTM engine for acquisition, activation, conversion, and retention. Own the P&L, pricing, packaging, and growth roadmap. The Ideal Candidate Independent Professional DNA: You know the independent/small practitioner market. You come from Intuit, Shopify, Square, Toast, GoDaddy, or similar. You understand the psychology and needs of solo operators. Scale-Up Builder: You have taken a business from early revenue to tens of millions. You know what breaks at each stage. AI Native: You think in terms of automation, leverage, and speed. GTM Operator: You know how to build SMB/solo-pro acquisition and conversion machines. Entrepreneur Energy: You want to build a category leader. You move fast. You embrace bold execution. Your Impact You will take a high-potential portfolio, shape the strategy, build the team, and turn our AI, data, and lead assets into the dominant platform for independent professionals. You will drive the shift from a strong B2C foundation into a blockbuster B2B engine. Smart, Fun, Get Things Done

Requirements

Independent Professional DNA: You know the independent/small practitioner market. You come from Intuit, Shopify, Square, Toast, GoDaddy, or similar. You understand the psychology and needs of solo operators.
Scale-Up Builder: You have taken a business from early revenue to tens of millions. You know what breaks at each stage.
AI Native: You think in terms of automation, leverage, and speed.
GTM Operator: You know how to build SMB/solo-pro acquisition and conversion machines.
Entrepreneur Energy: You want to build a category leader. You move fast. You embrace bold execution.