Schedule a call with a Leland team member who can help you explore your options.
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This package is designed for aspiring Chiefs of Staff who want to maximize their chances of landing a top offer. Through personalized 1-on-1 coaching with experienced professionals, you’ll be fully prepared for every stage of the recruiting process—from securing the interview to negotiating the final offer. Each engagement is tailored to your unique background and goals, with a focus on the skills and strategies most relevant to Chief of Staff roles. Whether you’re transitioning from consulting, finance, startups, or other strategy/operations roles, this package will give you the tools to stand out, excel in interviews, and confidently secure your next role as Chief of Staff. Some of the common coaching activities included in this package are: - Crafting standout resumes and cover letters tailored to Chief of Staff and strategic operator roles - Developing a personalized networking strategy to connect with executives and decision-makers - Optimizing your LinkedIn profile to highlight leadership, strategic thinking, and cross-functional experience - Deep dives into the Chief of Staff role, responsibilities, and success profiles at different types of companies - Mock case and scenario-based interviews focused on executive problem-solving, strategic planning, and organizational effectiveness - Behavioral interview prep to craft compelling stories that showcase leadership, adaptability, and impact - Company-specific preparation to demonstrate executive-level knowledge and alignment with leadership teams - Interview debriefs and iterative coaching to refine your approach - Building a strong personal narrative that positions you as an indispensable strategic partner - Insights into the Chief of Staff career path, progression, and common exit opportunities - Personalized timelines and milestones to keep your search structured and efficient - Customized follow-up strategies and offer negotiation coaching
A polished resume and cover letter that effectively highlight your strengths
A strategic networking plan to connect with industry professionals and alumni
An optimized LinkedIn profile that showcases your skills and experiences
Continuous feedback and improvement on all application materials
A detailed timeline and milestones to keep you on track throughout the application process
Techniques for standing out in competitive applicant pools
Coaching delivered via live sessions and .
Additional expectations or terms of engagement may be provided by coaches (e.g. expected response times, etc.).
Services included:
Interview Prep
LinkedIn Review
Strategic Planning
Promotion Strategy
Cover Letters
Resume Review
Networking Strategy
Salary Negotiation
Executive Support
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Get help with Strategic Planning, Salary Negotiation, and .
Stephen also coaches for Business Operations & Strategy and AI Automation & Agents. View all.

Joined November 2025
Land the Chief of Staff Role — Then Hit the Ground Running
I specialize in helping professionals land and thrive in Chief of Staff roles at high-growth technology startups — whether you're coming from consulting or finance and looking to make the leap, or you're already a CoS looking to level up. With hands-on experience as the Chief of Staff for two high-growth SaaS businesses, I've lived the transition from investment-driven work to operating at the center of a fast-moving business. The Chief of Staff role sits at a unique intersection - part strategist, part operator, part trusted advisor - and getting it right requires more than a strong resume. My coaching covers the full arc: figuring out whether the CoS role is the right fit for you, identifying the right company stage and CEO dynamic to target, building a compelling narrative around your background, and preparing you to interview with confidence for one of the most judgment-dependent roles in any organization. I combine practical frameworks with firsthand context - so you're not just ready to land the role, but to make an immediate impact once you're in it. If you're ready to make the leap into one of the most high-leverage seats in a startup, I can help you get there.
20h of coaching