GM, Marketplace at Leland

Job description

Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill for a world being rewritten by AI. We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us, and we've built a product that takes that seriously. We're looking for a high-agency operator to own a large, two-sided marketplace at the intersection of education, career development, and expert knowledge. You'll run the supply and demand engine across one of the broadest category footprints in the space, and increasingly with both human and AI experts serving customers. The Opportunity Leland is a marketplace where ambitious people find the experts and services they need to reach goals that actually matter. Getting into Harvard Business School. Landing a McKinsey offer. Passing the LSAT. Breaking into investment banking. Acing the MCAT. Pivoting into product management. Upskilling in AI to stay ahead in a fast-moving market. The category footprint is wide: MBA admissions, management consulting, private equity, investment banking, product management, law school, medical school, dental school, college admissions, master's programs, PhD programs, executive coaching, leadership development, career coaching, AI strategy, GMAT, GRE, LSAT, SAT, MCAT, USMLE, and dozens more, with thousands of customers working with Leland experts every month across all of them. The Marketplace GM owns the full business. That means owning supply (the quality, quantity, and activation of the expert network) and demand (the customers who come to Leland to find them). It also means expanding into new categories, developing enterprise partnerships (including early deals deploying AI experts for large-scale workforce upskilling), and finding the growth vectors that compound the platform over time. This is already an eight-figure business. The next GM takes it further. High ownership. Real P&L. Reporting to our Head of GMs. What You'll Own Expert Supply. The marketplace is only as good as the experts on it. You'll own the strategy for recruiting, vetting, activating, and retaining a high-quality bench of experts across every category, human and AI alike, because more great experts in more categories means more reasons for customers to come, stay, and refer. Customer Demand. You'll own how customers find Leland, why they convert, and how well they're served — understanding the acquisition funnel, optimizing conversion across categories, and ensuring the customer experience drives retention and word of mouth. Category Expansion. Leland currently serves 50+ categories spanning career development, school admissions, and test prep. There are more to open, and you'll identify where the demand exists, recruit the supply to serve it, and launch new categories with urgency. Enterprise. An early-stage but high-potential channel. Companies are coming to Leland to deploy AI-delivered services for workforce upskilling and outplacement at scale. You'll develop and grow this motion alongside the core marketplace. What We're Looking For Marketplace Operator You understand how two-sided markets work. You know that supply and demand both need dedicated attention, that the unit economics matter, and that growth comes from finding the right lever and pressing hard. You've done this before: at a startup, a marketplace company, or somewhere you had to figure it out yourself. Ideal backgrounds include: • GM, operator, or founder at a marketplace or platform business • Revenue or growth leader at an edtech, coaching, or content company • Early operator at a high-growth startup who owned a P&L or a major business line Commercially Sharp You've owned a number and moved it — carrying a quota, leading a sales or growth tea