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
$80110h of coaching
Crush the interview through mock interviews, personalized feedback, and more.
Starting at $6125h+ of coaching
Targeted coaching to help you break into Chief of Staff roles
Starting at $6125h+ of coaching
Get help with Interview Prep, LinkedIn Review, and .
Katy also coaches for MBA, Career Coaching, and Leadership Coaching. View all.
Joined January 2025
5.0
Former Chief of Staff (now COO) of YCombinator-Backed Startup
I'm an experienced startup Chief of Staff; I served as a fractional Chief of Staff for 10+ companies as a self-employed startup consultant, and later joined one of my clients (a YCombinator-backed leading Democratic political tech startup) in-house as founding Chief of Staff. I was later promoted to COO of the same company, which I've led for several years. Importantly, I've been an informal leadership coach and Chief of Staff mentor to numerous peers and junior staffers along my journey. I have formal experience developing a coaching and professional development program for second-in-command executives. I'm extremely familiar with the unique dynamics and demands of the Chief of Staff role - as a middleman between executives and staff, as a combined strategist-and-executor, and all of the other many ways that being a Chief of Staff is different than almost any other role in the professional world. I'm here to help you find a Chief of Staff role for the first time, and/or navigate a new role as a Chief of Staff.
20h of coaching