AI Instructor (Contract-to-Hire)

Job Description

Job Description

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.

Leland is hiring its first AI Instructor to teach and help shape the AI Builder Program, our fastest-growing product ever. This program takes people from complete beginner to genuinely capable AI practitioners, and it works because the instruction is exceptional. We need someone who can make that happen.

This is a contractor role to start, with a real path to full-time conversion as the program scales. You will lead live cohort sessions, collaborate directly with our curriculum team, and play a meaningful role in how the program evolves over time.

This role is right for someone who loves to teach, has done it at scale, and is genuinely excited about AI. You don't need to be a deep technical expert. You do need to be curious, fast-learning, and the kind of instructor who turns a room of skeptics into believers.

We're building something significant here. If you want to be part of defining what world-class AI education looks like, we'd love to talk.

• Lead live sessions of the AI Builder Program, guiding cohorts of professionals from beginner to advanced AI fluency

• Deliver smooth, confident live demos of AI tools and software, keeping sessions engaging even when technology behaves unexpectedly

• Make complex concepts feel simple and accessible, meeting learners where they are

• Create a classroom environment where people feel safe to experiment, ask questions, and stretch beyond their comfort zone

• Work closely with Leland's curriculum team to refine and improve program content across all sessions

• Share real-time feedback from cohorts to help the curriculum evolve quickly

• Contribute ideas for new material, exercises, and delivery formats based on what you observe in the room

• Participate in curriculum design conversations and bring an instructor's perspective to every decision

• Stay current on AI tools, trends, and use cases, bringing fresh examples and context into every session

• Develop your own fluency with Leland's full AI stack so you can teach from a place of genuine understanding

• Help define what excellent AI instruction looks like at Leland as we scale

• 5+ years of experience in an instructional role, whether that's teaching, training, facilitation, or a similar format with consistent group delivery

• Proven ability to teach large groups (100+ students or participants) and hold a room

• Strong comfort with live software demos and navigating complex tools in real time, in front of an audience

• Genuine curiosity about AI and a clear willingness to go deep on it; you don't need to be an expert today, but you need to want to become one

• Excellent communication skills: clear, confident, and able to adapt to any audience

• A collaborative, low-ego approach to working with a curriculum team

• Former or current educators are welcome, but this background is not required; we care far more about instructional quality and AI enthusiasm than credential

• If converted to full-time, this position would require relocation to Utah

This is a contractor engagement to start. Compensation is competitive and structured to reflect the value of the role. For the right person, this is designed to grow into a full-time W2 position as the program scales.

• 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.