Jobs · Management · Illinois

Executive Assistant

Waterstone Human Capital · Chicago, IL · 2 mo ago
HybridManagementFull-time

About the role

Our client is a high-profile, multi-industry entrepreneur who leads several ventures simultaneously, sits on corporate and nonprofit boards, and maintains an active public platform through media, speaking engagements, and published work. She is seeking a high-level Executive Assistant who understands the pace and complexity of supporting a multi-company entrepreneur and can operate with full ownership of her time, priorities, and follow-through. This is not an entry-level or basic administrative role. The ideal candidate has already supported a principal at this level, anticipates needs before they are voiced, and is comfortable managing ambiguity across several businesses at once.

Responsibilities

  • Serve as the primary gatekeeper of the executive's time and attention, protecting strategic priorities and shielding her from lower-value demands.
  • Manage a complex, shifting calendar across multiple companies, board commitments, and speaking engagements, with the judgment to anticipate conflicts and prep needs in advance.
  • Own inbox triage and follow-through so nothing is dropped; proactively flag what needs attention and independently resolve what does not.
  • Track and drive forward active projects, using tools such as Gantt charts to manage timelines, vendors, and deliverables across multiple initiatives.
  • Support an active capital raise by coordinating with the investor relations lead, following up on outstanding items, and helping move documentation and communications forward.
  • Coordinate board meeting logistics and preparation, ensuring materials and the executive's time are handled with precision.
  • Manage speaking engagement logistics end-to-end, including coordination with speaker bureaus, event organizers, and travel.
  • Communicate proactively and concisely, giving short, clear briefs rather than requiring the executive to chase status updates.
  • Build and maintain vendor and supplier relationships as new projects or ventures require.

Requirements

  • 5+ years supporting a C-level executive, founder, or entrepreneur, ideally across multiple entities or a fast-moving portfolio of businesses.
  • Demonstrated ownership of an executive's calendar, inbox, and project pipeline with minimal oversight; a track record of "I've got this" follow-through.
  • Strong organizational and project management instincts; experience with tools like Gantt charts or similar tracking systems is a plus.
  • Sound judgment and discretion, with the ability to triage competing priorities in a high-volume, fast-paced environment.
  • Exposure to investor relations, fundraising support, board administration, or speaking/PR coordination is a strong plus.
  • Comfortable working with a founder who moves quickly and expects a partner who can keep pace, not someone who needs to be managed.
  • Prior experience supporting an entrepreneur in a build phase (multiple ventures, high growth) preferred; restaurant, hospitality, or media industry exposure is a plus but not required.

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