Skip to main content

Get started with an expert

All Chief of Staff Experts

Book one-on-one time with an expert coach to make progress on your goals.

  • Gwen T.

    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.

    $299/hr

    Available Sep 23, 2026

  • Derek E.

    Derek Ewald

    5.0

    (7)

    3,045 min coaching

    How to be the best Chief of Staff at a startup

    Welcome to my profile! With a robust background in management consulting at Bain & Company, where I served as a Senior Associate Consultant, and my role as Chief of Staff and VP of Strategy and Corporate Development at BioLite, I bring a wealth of experience to my coaching practice. My journey has equipped me with the strategic insights and leadership skills necessary to excel in high-impact roles. I specialize in guiding aspiring Chiefs of Staff to navigate their career paths effectively, leveraging my firsthand experience in both consulting and executive support. Whether you're looking to refine your strategic thinking, corporate development / M&A, or enhance your leadership capabilities, I'm here to help you achieve your career goals. Let's connect and chart your path to success!

    $129/hr

    Available Sep 21, 2026

  • Hannah E.

    Chief of Staff across media, government & nonprofit

    Over the better part of a decade, I've done nearly every kind of work that falls under the Chief of Staff umbrella — across media, government, and the nonprofit sector. At the White House, I managed executive logistics and high-stakes international engagements for the Office of the U.S. Trade Representative. At DHS, I led appointee hiring and management across the Department — including FEMA, TSA, and other components — before being promoted to Chief of Staff for the Office of Policy. In media, I served as Chief of Staff for Politico Live and later as Executive Director of Operations at Protocol. I now serve as Chief of Staff at a national nonprofit. Across all of it, the throughline has been the same: getting handed an ambiguous, high-stakes mandate — do X by Y date, with Z resources, no playbook — and being trusted to build the plan and execute it. That range is exactly what makes me useful as a coach. Most Chief of Staff advice comes from people who've only seen the role in one context. I've operated inside newsrooms, federal agencies, and mission-driven organizations, which means I can help you separate what's universal about the job (earning trust with a principal, operating across a whole org without a functional lane, translating ambiguity into a plan) from what's specific to any one industry. Whether you're trying to land your first Chief of Staff role or you're already in the seat and want to expand your scope and grow your influence, I'd love to help — bringing the same practical, get-it-done approach to coaching that I bring to the job itself.

    $120/hr

    Available Sep 23, 2026

  • Tiffany T.

    CoS to multiple fintech CEOs with unicorn valuations

    Inaugural Chief of Staff to Founder & Group CEO of OakNorth Bank UK ($2.8B valuation) Special Projects for the CEO, Jump.ai

    $500/hr