United States · Remote Solely
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 he…
Skills: Strategic Planning, Executive Support, AI Fundamentals, AI Automation, Resume Review
United States · Remote Solely
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 he…
Skills: Blockchain Strategy, Cryptocurrency Fundamentals, Smart Contracts, Decentralized Applications, Web3 Development
United States · Remote Solely
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 he…
Skills: Chess Coaching, Board Game Coaching, Game Analysis, Opening Repertoire Development, Middlegame Strategy
United States · Remote Solely
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 he…
Skills: College Admissions Coaching, Application Strategy, Essay Editing, School Selection, Interview Preparation
United States · Remote Solely
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 he…
Skills: CISSP Certification, Tutoring, Teaching, Mentoring, Cybersecurity
United States · Remote Solely
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 he…
Skills: Climate Consulting, Corporate Sustainability, Sustainable Supply Chain, Climate Policy, Grant Writing
United States · Remote Solely
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 he…
Skills: Business Development Strategy, Partnership Development, Market Analysis, Negotiation, AI Automation
United States · Remote Solely
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 he…
Skills: Public Speaking, Communication Coaching, Presentation Skills, Active Listening, Nonverbal Communication
United States · Remote Solely
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 he…
Skills: Business Strategy, Operations Management, Process Improvement, Project Management, Financial Analysis
United States · Remote Solely
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 he…
Skills: Stand-up Comedy, Improv Training, Comedy Writing, Performance Coaching, Audience Engagement
United States · Remote Solely
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 he…
Skills: Career Coaching, Job Search Strategy, Resume Review, Cover Letter Guidance, Interview Preparation
United States · Remote Solely
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 he…
Skills: CFP Exam Coaching, Financial Planning, Tutoring, Mentoring, Study Planning
United States · Remote Solely
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 he…
Skills: Sales & Trading Strategy, Trading Execution, Financial Modeling, Risk Management, Market Analysis
United States · Remote Solely
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 he…
Skills: Data Analysis, Statistical Analysis, Data Visualization, Business Intelligence, Market Research
Lehi, Utah, United States · On-site
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 he…
Skills: Demand Generation, B2B Marketing, Consumer Marketing, Brand Strategy, Content Strategy
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Mentor clients on breaking into or growing within Chief of Staff and executive support roles by teaching strategic planning and AI tools. Provide career guidance including resume reviews, interview preparation, and salary negotiation strategies.
Candidates must have hands-on experience as a Chief of Staff, Executive Business Partner, or in a similar executive support role. A proven track record of driving organizational initiatives and a structured approach to coaching are required.
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.
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.
Join millions of people reaching ambitious goals, building with AI, and leveling up their teams.
Leland is a platform that helps individuals and businesses win in the age of AI. Powered by thousands of experts, Leland provides customers with the support they need to own their future.
Offices: Stanford, CA 94305, US
Join millions of people reaching ambitious goals, building with AI, and leveling up their teams.
Leland is a platform that helps individuals and businesses win in the age of AI. Powered by thousands of experts, Leland provides customers with the support they need to own their future.
Offices: Stanford, CA 94305, US
