Land a Chief of Staff Offer — Complete Package

Land a Chief of Staff Offer — Complete Package

Offered by Gaylan G.

✨ You're Chief of Staff coach with 11 years of Naval Leadership experience

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Studied at United States Naval Academy

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Worked at Airspeed

Package Description:

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


What you'll get from this package

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


Additional details

Coaching delivered via live sessions and .

Refund Policy

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


Gaylan G.

Offered by Gaylan G.

Joined October 2021

✨ You're Chief of Staff coach with 11 years of Naval Leadership experience

With extensive experience in strategic leadership and operational excellence, I am exceptionally qualified to serve as a Chief of Staff Coach on Leland, guiding professionals seeking to excel in this pivotal role. My background includes over 11 years as a Naval Officer, culminating in my position as Deputy Chief of Staff to the Navy Chief of Legislative Affairs, who reports directly to the Secretary of the Navy and the Chief of Naval Operations. In this capacity, I collaborated closely with US Senators/Congressmen and Senate/House Committee staff, managing high-stakes legislative initiatives and ensuring alignment across executive branches. Complementing this, my five years in product management at leading tech companies such as Amazon, LinkedIn, and Guideline have refined my expertise in cross-functional coordination, strategic planning, and driving organizational priorities to achieve measurable results. As a coach, I am dedicated to empowering people to break into the Chief of Staff role and enhance their strategic leadership capabilities. My approach draws from proven experience as a strategic partner in executive stakeholder management, optimizing operational workflows, and delivering high-impact organizational outcomes in dynamic environments. By providing tailored guidance on frameworks such as OKRs, stakeholder mapping, and strategic communication, I equip people with the tools to articulate their value, build executive trust, and navigate complex challenges effectively. My commitment is to offer people actionable strategies and personalized mentorship to realize their Chief of Staff aspirations with confidence and precision.

Experience level: Director

$1,104

20h of coaching

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    Land a Chief of Staff Offer — Complete Package by Gaylan G. | Leland