GM, Marketplace

About the role

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.

Responsibilities

• 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.

Requirements

• Marketplace Operator
• 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
• Category Instinct
• AI-Native
• You build with AI in your own work. You're not learning about it from the outside; it's already part of how you operate. That's table stakes here.
• Your Identity
• You find the pull. You're not waiting to be told which lever matters; you're testing, reading the data, and doubling down on what's working.
• You're a builder. You don't just manage what exists. Y

Benefits

Additional Information

Leland's mission is to unlock human potential by making the world's expertise more accessible. Our platform connects ambitious people with coaching, content, and courses that can can help them achieve their career and educational goals. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals, raised $19M from world-class investors, and built the industry leader in educational, career, and AI coaching. 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.

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