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 Comedy, Stand-Up & Improv Coach to work with clients looking to develop and grow their comedy careers. This role includes teaching core stand-up comedy techniques, improv training, and comedy timing, as well as helping clients sharpen their joke writing and comedy writing skills. Coaches also support clients with performance coaching, audience engagement, and branding for comedians, along with practical guidance on open mics, show production, and touring strategy. On the career side, coaches offer resume review, LinkedIn review, and cover letter guidance, plus interview prep, networking strategy, and salary negotiation, along with broader skill building and support for those pursuing freelancing opportunities in comedy. Ideal candidates have hands-on experience in stand-up, improv, or comedy writing (as a performer, writer, or industry professional), a strong understanding of what it takes to succeed on stage and build a comedy career, and a clear, structured approach to coaching clients through both craft and career growth. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every client.

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.