Joblaze summary

The Chief of Staff Mentor at Leland focuses on guiding clients aiming to enter or advance in chief of staff and executive support roles through strategic planning and the application of AI tools. Candidates should possess substantial experience in executive support roles and demonstrate a structured coaching approach to help clients with career development, including resume and interview preparation. This position is ideal for seasoned professionals who thrive in a dynamic, collaborative environment and are passionate about empowering others to achieve their ambitions.

Joblaze insights

Listed about 2 months ago — first seen on Joblaze September 3, 2026. Last confirmed on Leland's careers page November 2, 2026.
AI/ML appears in 17.3% of 1579 comparable senior management roles.

Quick facts

Is the Chief of Staff Mentor role remote?: Yes — Leland lists this as a fully remote position.
What's the tech stack?: Joblaze extracted these technologies from the posting: AI/ML.
What seniority level is this role?: Leland targets senior candidates for this position.
Is this full-time or contract?: Freelance for this Chief of Staff Mentor role at Leland.

From the original posting

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
Operate in a fast-paced, AI-native environment

Standard company text repeated across Leland's postings is omitted here.

Chief of Staff Mentor

Why Leland?

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