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Executive Assistant, Chicago, IL (Hybrid)

Executive Assistant, Chicago, IL (Hybrid)

Reporting directly to the CEO, this role drives the operating rhythm that keeps the leadership team aligned and key priorities moving forward. More than a traditional gatekeeper, you’ll serve as a trusted extension of the CEO, exercising sound judgment, anticipating needs, and ensuring seamless execution in a fast-paced, high-growth environment.

While primarily focused on executive and business support, the role may occasionally include personal logistical assistance such as travel coordination, scheduling, or family-related support, requiring flexibility and a true partnership mindset.

Responsibilities

  • Own the CEO’s calendar end-to-end, not just scheduling, but strategic prioritization. Protect focus time, sequence meetings intentionally, and ensure every day reflects what matters most.
  • Serve as a trusted proxy between the CEO and internal teams, investors, board members, customers, and partners. Draft, manage, and triage executive communications with discretion and precision.
  • Plan and manage complex domestic and international travel–multi-city itineraries, visas, ground transport, and last-minute changes, with zero dropped balls.
  • Coordinate board meetings, investor updates, and exec-level offsites end-to-end, including materials prep, logistics, and follow-through on action items.
  • Track CEO commitments, follow-ups, and open loops across the organization. Anticipate what’s coming, flag what needs attention, and keep priorities visible.
  • Take on light chief of staff responsibilities, preparing briefing documents, synthesizing context before key meetings, and helping the CEO show up fully prepared.
  • Partner closely with the broader leadership team and department heads to facilitate alignment, information flow, and timely decisions.
  • Handle sensitive business information — personnel matters, deal discussions, strategic plans — with the highest level of discretion.
  • Manage expense reporting, contract routing, vendor coordination, and other operational tasks that keep the executive office running smoothly.

Ideal Experience

  • 5–7 years of Executive Assistant experience supporting a CEO, Founder, or senior executive within a high-growth startup or tech environment.
  • Proven ability to operate as a trusted partner to fast-moving leaders, balancing discretion, sound judgment, and proactive problem-solving.
  • Exceptional communication skills with experience drafting executive-level communications, investor updates, and internal messaging.
  • Highly organized, relationship-driven, and comfortable navigating dynamic, evolving organizations with professionalism and warmth.
  • Tech-savvy and operationally minded, with strong proficiency in tools like Google Workspace, Slack, Zoom, JIRA, and AI-enabled productivity platforms.
  • Experience supporting periods of rapid growth, with exposure to board operations, investor relations, fundraising, or Chief of Staff-style responsibilities preferred.
  • Background in AI, ML, or deep tech environments is a plus.

#118024

Up to $150,000 salary per year (based on experience)

Apply Online.