Land a Chief of Staff Offer — Getting Started

Land a Chief of Staff Offer — Getting Started

Offered by Gwen T.

5.0

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Stanford MBA & PE-Backed COO | Coach for Aspiring & Current Chiefs of Staff

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Studied at Stanford Graduate School of Business

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Works at CoreStream

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


Gwen T.

Offered by Gwen T.

Joined August 2025

5.0

Stanford MBA & PE-Backed COO | Coach for Aspiring & Current Chiefs of Staff

I’ve built and scaled teams at the highest levels of private equity–backed companies, where the Chief of Staff role is pivotal to aligning executives, driving priorities, and ensuring execution. With my background as a Stanford MBA and President/COO, and as a former CoS myself, I understand how exceptional Chiefs of Staff operate—and what separates a trusted strategic partner from a task manager. I coach both aspiring and current Chiefs of Staff on how to structure the role, build trust with executives, and translate vision into action. From setting up operating cadences and managing board prep to driving cross-functional initiatives, my approach blends practical playbooks with leadership insights. You’ll leave with the clarity and confidence to add measurable value from day one and grow into your next leadership opportunity.

Experience level: Executive

Starting at $1,420.25

5h+ of coaching

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    Land a Chief of Staff Offer — Getting Started by Gwen T. | Leland