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 Opportunity 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 the company 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 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 Travel Percent Less than 10% Functions General Management Skills General Management required