[Hiring] Chief of Staff Mentor @Leland

Role Description

Leland is 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.
• Helping clients apply emerging tools like AI fundamentals and AI automation to their work.
• Supporting clients on the career side, offering:
  • Resume review
  • LinkedIn review
  • Cover letter guidance
  • Interview prep
  • Networking strategy
  • Salary negotiation
  • 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.
• 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.

Qualifications

• Experience as a chief of staff or in executive support.
• Strong track record of driving initiatives.
• Structured coaching approach.

Requirements

• Hands-on experience in relevant roles.
• Ability to teach strategic planning and executive support skills.
• Familiarity with AI fundamentals and automation tools.

Benefits

• 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.
• Opportunity to make a great company.

Company 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.