Chief of Staff Mentor

Leland; United States; Remote; USD 55,000 - 124,000; Full time

Job summary

Leland is seeking an experienced Chief of Staff Mentor to coach clients aiming to break into or grow within chief of staff and executive support roles. You will teach core strategic planning and executive support skills, as well as helping clients apply emerging tools like AI fundamentals and AI automation to their work.

Coaches also support clients on the career side, offering resume review, LinkedIn review, and cover letter guidance, along with interview prep, networking strategy, salary

Qualifications

• Hands-on experience as a chief of staff or in executive support roles.
• Proven ability to drive initiatives across an organization.
• Structured, methodical coaching approach.

Responsibilities

• Teach core strategic planning and executive support skills to clients.
• Help clients apply AI fundamentals and AI automation to their work.
• Provide resume, LinkedIn review, and cover letter guidance, plus interview preparation.
• Offer networking strategy, salary negotiation, and promotion guidance tailored to chief of staff roles.
• Set your own hours and rates; host sessions virtually; collaborate with our team to deliver high-quality coaching.

Skills

Executive coaching

Strategic planning

Communication

Networking

Job description

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 Chief of Staff Mentor to work with clients looking to break into or grow within chief of staff and executive support roles. This role includes teaching core strategic planning and executive support skills, as well as helping clients apply emerging tools like AI fundamentals and AI automation to their work. Coaches also support clients on the career side, offering resume review, LinkedIn review, and cover letter guidance, along with interview prep, networking strategy, salary negotiation, and promotion strategy tailored to chief of staff roles. Ideal candidates have hands-on experience as a chief of staff or in executive support (as a chief of staff, executive business partner, or industry professional), a strong track record of driving initiatives across an organization, and a clear, structured approach to coaching clients through both technical 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 make a great company

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