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Leland

Chief of Staff Mentor

Remote - USA

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hirly's read of this role

Role family
Operations
Seniority
Executive
Country
US
Work mode
Remote-friendly
First seen by hirly
1 Sept 2026

Derived automatically from the posting. Upload your resume above to see how the role scores against it.

the posting

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 to make a great company

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

Original posting on Leland's site ↗

Listed on hirly, a job board. hirly is not the employer: Leland is hiring for this role.

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