GM, AI Services

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 an AI-native founder-type to build Leland's AI Services business from the ground up. You'll own the P&L, close clients, build the service delivery model, and marshal resources to rapidly scale the business. If you've considered building an AI services agency (or already built one) and want equity in a rocket ship, a faster pace, and a bigger platform to scale from, this is your role.

Leland is one of the fastest-growing AI education companies in the country. Through our AI Builder Program, we train professionals, operators, and executives to build real AI-powered workflows and automations. That training pipeline is producing something we're now ready to monetize at scale: a growing roster of companies who want to hire someone to build for them.

We're already delivering AI services for external clients. Companies have come to us for strategy sessions, workflow implementation, and agent architecture; the inbound keeps growing every week. Companies are desperate for people who can actually build, not just advise. We have those people, both internal employees and third-party experts on Leland. We need a GM to turn this into a real business.

This is a net-new role. You'll be the first dedicated hire on AI Services, reporting to our Head of GMs, with full ownership of the business line and meaningful variable compensation and equity upside.

You need to be able to evaluate a client's architecture, scope implementation work accurately, and QA what your team builds. You don't need to write every line, but you need to know when something is wrong and why. That means one or more of:

• A portfolio of complex AI builds (agents, automation workflows, n8n or similar pipelines, MCP integrations) that you can walk us through

• Meaningful work experience in software engineering, data, or technical product

• A technical academic background or self-taught technical path

The bar is: could you give a client a credible architecture recommendation on your first call with them? If yes, you're technical enough.

You've owned a number and moved it. That could mean you've founded a company, run a business line, carried a sales quota, or led a revenue-generating team. The pattern we're looking for is: you identified an opportunity, built a motion to go get it, and closed it yourself.

The ideal candidate has already built an AI services firm. You know what the sales cycle looks like, you've scoped projects, you've managed client expectations, and you know what a repeatable delivery model takes. You want to be somewhere that's moving faster, at a bigger scale, with a platform behind you.

• You think in systems. You're not just trying to close the next deal, you're building the machine that closes the tenth and the hundredth.

• You're comfortable being early. There's no playbook handed to you. You'll write the first one.

• You sell by knowing more than the buyer. Your credibility comes from technical depth, not from pitch decks.

• You're gritty. You'll take the intro call, scope the project, manage the delivery, and follow up on the invoice if you have to.

• You move fast. When something is a priority, it happens now.

• You're a builder. Your instinct is to prototype something, not to schedule a meeting to discuss it.

• The chance to join a world-class team helping people achieve their career and educational dreams

• Work in a collaborative, high-energy environment where your contributions have a direct impact

• Operate in a fast-paced, AI-native environment

• We don't hire people who merely want to work for a great company; we hire people who want to make a great company

Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.