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 seeking an experienced small business coach to work with entrepreneurs building and growing their own businesses. This role includes guiding owners through business operations, financial planning, financial accounting and reporting, and hiring, as well as building a strong sales strategy and customer service approach. Coaches also support growth through digital marketing, social media strategy, web development, and applying AI fundamentals, AI agents, and AI automation to modern business operations. Ideal candidates have professional experience running or advising small businesses, prior coaching or mentoring experience, and a clear, structured approach to helping owners navigate both the operational and strategic sides of their business. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every business owner.

Why Leland?

• 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.