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)

