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Description
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
What you'll get from this package
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
Additional details
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:
Resume Review
Networking Strategy
Interview Prep
Strategic Planning
LinkedIn Review
Cover Letters
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
More packages from Jeffrey
Custom hourly · $150/hr
Jeffrey also coaches for Product Marketing, Business Operations & Strategy, Career Coaching, Management Consulting, and MBA. View all.

Offered by Jeffrey W.
Joined December 2021
Former Chief of Staff at Eko Health | Member of Chief of Staff Network
I can coach on the Chief of Staff role because I’ve held the position myself for two years and am active in the Chief of Staff Network. Having both firsthand experience and insight from interviewing for multiple Chief of Staff roles previously, I deeply understand the nuances, expectations, and pathways to success in this position. I'd love to help you select a role, prepare for an interview, or uplevel your skillset.
$712.50 - $1,350
5h - 10h of coaching