Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
This package is designed for candidates pursuing Chief of Staff roles who want focused, high-impact support throughout the recruiting process. Whether you’re breaking into the Chief of Staff world for the first time or looking to secure a more senior, strategic role, this package is built to meet you where you are and help you stand out. Available in 5- or 10-hour formats, you’ll work 1-on-1 with an expert coach to target the areas that matter most—from sharpening your executive narrative to preparing for case and scenario-based interviews to navigating final offer negotiations. Each session is tailored to your unique background and goals, giving you the clarity and confidence needed to land your ideal role. Common coaching activities include, but are not limited to: - Resume & LinkedIn review: Position your experience to highlight leadership, strategic impact, and cross-functional influence - Storytelling & narrative development: Build a compelling personal narrative that resonates with executives and boards - Recruiting strategy: Identify high-potential roles and companies that align with your skills, values, and career trajectory - Interview preparation: Practice scenario-based and behavioral Chief of Staff interviews, with targeted feedback to refine your responses - Networking & outreach strategy: Develop an intentional plan to connect with executives and hiring managers - Company- & executive-specific prep: Conduct deep dives into leadership priorities and organizational challenges to tailor your approach - Offer negotiation: Navigate compensation and scope conversations strategically to set yourself up for long-term success
Tailored resume and LinkedIn optimization for Chief of Staff roles
Help crafting a compelling, strategic candidate narrative
Company and role targeting aligned with your skill set and interests
Preparation for business operations specific interview formats
Support for networking, follow-ups, and offer negotiation
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
Cover Letters
Resume Review
Networking Strategy
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
$80110h of coaching
Expert help on everything from getting the interview to landing the offer.
$2,06420h of coaching
Crush the interview through mock interviews, personalized feedback, and more.
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.
5h+ of coaching