General Manager

General Manager About the Company A 20-plus-year company using AI trained on real human expertise to power the future of independent professional work Industry Computer Software Type Privately Held, VC-backed Founded 2019 Employees 51-200 Funding $51-$75 million Specialties machine learning dental software artificial intelligence dental radiology pathology detection medical device software clinical performance software diagnostic technology dental practice management and computer vision About the Role The OpportunityA 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 OwnGeneral Management & P&LFull 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 impactGo-to-Market Strategy & ExecutionDesign, 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 successDevelop and operationalize a repeatable vertical launch playbook, from market selection and positioning through execution, measurement, and iterationAnticipate 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 happenedTranslate customer insights and performance data into sustained revenue growth, turning qualitative and quantitative signals into clear priorities, experiments, and scalable growth motionsProduct Operations & Cross-Functional LeadershipPartner 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 integratedEstablish operating cadence, KPIs, and governance that enable fast execution without unnecessary bureaucracyBe 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 scalesExternal LeadershipRepresent the company externally with partners, at conferences, and within the independent professional ecosystemBuild strategic partnerships that accelerate distribution, credibility, and adoption What Success Looks LikeFirst 90 DaysDeep understanding of the customer, market, product, and revenue mechanicsIdentification and activation of the highest-impact near-term revenue leversDelivery of a clear GTM roadmap, hiring plan, and initial pricing and packaging hypotheses6 MonthsDemonstrable acceleration in acquisition, conversion, and revenue velocityEarly proof points that the vertical playbook is repeatableOperating cadence, KPIs, and team structure in place to support scale12 MonthsA validated path toward unlocking the broader $100M+ opportunityPearl positioned as a category-defining platform for independent professionals The Ideal CandidateRequired ExperienceGM- or VP-level leader with full P&L ownershipProven experience scaling a B2B, SaaS, marketplace, or platform business from early revenue to tens of millionsDeep understanding of SMB, microbusiness, or solo professional marketsHands-on GTM operator with experience building acquisition and conversion enginesComfortable operating in zero-to-one and one-to-many environments with incomplete playbooksStrongly Aligned BackgroundsExperience 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 scratchExperience building or commercializing AI-powered productsLeadership ProfileEntrepreneurial, high-ownership mindset with a bias for actionComfortable with ambiguity and capable of bringing clarity quicklyData-driven, customer-obsessed, and outcomes-orientedWilling to operate at both strategic and executional levelsNice to HaveMarketplace, lead-generation, or freemium business model experienceExperience in legal tech or related vertical SaaS markets serving independent professionalsFounder experience with strong learning velocityExperience leading businesses as GM, Head of B2B, VP GTM, or similarWhy JoinTrue ownership: a GM role with real authority and accountabilityA massive market opportunity at the intersection of AI and independent professionalsAbility to shape product, GTM, and team from the ground upBacked by an established consumer platformA rare opportunity to build a category-defining business, not just optimize an existing one Travel Percent Less than 10% Functions General Management Skills General Management required