Chief of Staff Mentor

The role

This person will teach core strategic planning and executive support skills to clients. They will help clients apply AI fundamentals and AI automation to their work and provide career support including resume review and interview prep.

What you will do

• Teach core strategic planning and executive support skills
• Help clients apply AI fundamentals and AI automation to their work
• Support clients on the career side
• Offer resume review, LinkedIn review, and cover letter guidance
• Provide interview prep, networking strategy, salary negotiation, and promotion strategy

Required qualifications

• Hands-on experience as a chief of staff or in executive support
• Strong track record of driving initiatives across an organization
• Clear, structured approach to coaching clients through both technical and career growth

Nice to have

• Experience as an executive business partner or industry professional

Benefits

• The chance to join a world-class team helping people achieve their career and educational dreams
• Work in a collaborative, high-energy environment
• Operate in a fast-paced, AI-native environment

About the company

Leland connects people with experts, programs, and communities to land jobs, get into school, or upskill. Since 2021, they have helped tens of thousands of people and raised $19M.