Quartermaster

Executive Assistant to the CEO

Remote, United States remote Entry Salary not listed
remote Technology & IT Curated
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About the role

About the Role:
We're looking for a battle-tested Executive Assistant to partner directly with our CEO. Someone who has spent years in high-growth, Series A-and-beyond startups and knows what that pace demands. This isn't an entry-level support role. We need someone who has seen productive chaos before, isn't rattled by it, and treats it as raw material to build order from. You'll be the CEO's key asset for managing time, and priorities so nothing important slips and nothing urgent gets missed.
What You'll Do:

Own the CEO's calendar end-to-end — ruthlessly prioritizing competing demands across board members, investors, customers, and internal leadership.

Anticipate needs before they're asked; you're often three steps ahead, not reacting to the last request.

Coordinate complex, fast-changing travel logistics (domestic and international) with zero hand-holding.

Act as a trusted gatekeeper and first point of contact for the CEO, managing sensitive and confidential information with discretion.

Build and maintain systems —calendars and follow-up loops — that bring structure to a fast-moving, often ambiguous environment.

Coordinate cross-functionally with leadership, finance, and People teams on scheduling, offsites, board meetings, and special projects.

Manage expenses, vendor relationships, and ad hoc administrative or personal tasks as needed.

Jump into whatever fire needs putting out — this role is not static, and the job description will evolve as the company does.

What We're Looking For:

7+ years of experience as an Executive Assistant supporting a C-level executive, ideally a CEO or founder, at a Series B or later venture-backed startup.

A proven track record of thriving in high-growth, high-ambiguity environments — you've supported a company through scaling, fundraising, and organizational change.

Exceptional judgment and discretion; you can be trusted with highly confidential information without a second thought.

Elite organizational skills — you build the systems and processes that don't yet exist, rather than waiting to be told how.

Calm under pressure. Ambiguity and last-minute changes don't throw you off; you find the signal in the noise.

Excellent written and verbal communication — you can represent the CEO's voice accurately and professionally.

A bias toward action and ownership — you solve problems rather than escalate them, and you know the difference between the two.

Comfortable working long or unpredictable hours occasionally, and available outside standard business hours when true urgency requires it.

Tech-savvy across calendar, travel, communication, and productivity tools (e.g., Google Workspace, Slack, Notion, expense platforms); quick to adopt new tools.

Nice To Have:

Experience supporting a CEO through a board cycle, fundraise, or major company milestone (e.g., Series C, IPO prep, acquisition).

Background in a fast-paced tech or AI company.

Experience managing a small team of support staff or coordinating with other EAs/executive support functions.

Why Join Quartermaster AI
You'll work at the center of the company, with direct visibility into strategy, board dynamics, and how a high-growth company is really built. This role has real influence — the person in this seat helps set the pace and the tone for how the whole leadership team operates.
Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Role
Technology & IT Finance Operations Remote Collaboration Executive Assistant remote

Likely questions

  1. Tell us about work you have done that is close to the Executive Assistant to the CEO role.
  2. How would you approach your first 30 days at Quartermaster?
  3. Which of Finance, Operations and Remote Collaboration have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you stay organised and communicate clearly when working remotely?

Prepare before the call

  • A recent example that proves your experience with Finance, Operations and Remote Collaboration.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Executive Assistant to the CEO role because I can bring practical experience in Finance, Operations and Remote Collaboration, learn the team quickly, and contribute to the outcomes Quartermaster needs from this hire.

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