Land a Chief of Staff Offer — Getting Started

Land a Chief of Staff Offer — Getting Started

Offered by Cassandra D.

Chief of Staff at OpenAI | Stanford MBA & Harvard MPP

Stanford Graduate School of Business Logo

Studied at Stanford Graduate School of Business

OpenAI Logo

Works at OpenAI

Package 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 .

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

Cover Letters

Resume Review

Networking Strategy


Cassandra D.

Offered by Cassandra D.

Joined July 2021

Chief of Staff at OpenAI | Stanford MBA & Harvard MPP

Welcome to my profile! With a diverse background spanning top-tier institutions and leading organizations, I bring a wealth of experience to my role as a Chief of Staff coach. Currently serving as Chief of Staff at OpenAI, I have honed my strategic and operational skills, building on my previous experiences as a Summer Associate at McKinsey & Company and a Program Manager at Google. My academic journey includes an MBA from Stanford Graduate School of Business and an MPP from Harvard University, where I developed a strong foundation in leadership and public management. I am passionate about helping aspiring Chiefs of Staff navigate their career paths, leveraging my insights from both the tech and consulting industries. Let's connect to craft a personalized strategy for your success!

Experience level: Manager

Open to working with clients outside the U.S.

Starting at $612

5h+ of coaching

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