Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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
Targeted coaching to help you break into Chief of Staff roles
Starting at $6705h+ of coaching
Crush the interview through mock interviews, personalized feedback, and more.
Starting at $6705h+ of coaching
Starting at $7455h+ of coaching
Get help with Strategic Planning, Executive Support, and .
Cherizza also coaches for Business Operations & Strategy and Leadership Coaching. View all.

Joined May 2025
5.0
Former C-Suite Chief of Staff @ Google, Stitch Fix, Intel I Get The Role
As a Chief of Staff to 8 different C-level executives and a strategic leader, I've honed my skills in driving organizational transformation and operational efficiency. My experience includes serving as Chief of Staff to the CEO at Stitch Fix, where I led through two CEO transitions and managed internal communications and change management across the enterprise. At Google, I was part of the Office of the CEO's Proactive Issue Management team, handling responses to global and social crises. As a founder and CEO of my own advising firm, I am passionate about helping leaders integrate technology and people effectively. In all my CoS roles, I was the first and established the precedent and then grew to lead the Strategy or Business Operations function as a whole. If you're looking to excel in a Chief of Staff role or enhance your strategic impact, let's connect and explore how I can support your journey!
20h of coaching