We need an EA who thrives in ambiguity, can anticipate needs before they're voiced, and acts as a force-multiplier for our founding team. This isn't a traditional EA role — you'll be embedded in the business.
Responsibilities
- Own the CEO and founding team's calendars, travel, and communications with zero drama
- Prepare briefing materials, meeting agendas, and board-level presentations
- Track action items across cross-functional projects and keep leadership accountable
- Manage vendor relationships, office logistics, and ad hoc operational needs
- Handle sensitive information and communications with complete discretion
- Support recruiting coordination, onboarding logistics, and team events
- Act as a communication hub — routing the right information to the right people
Requirements
- 4+ years as an EA or Chief of Staff, ideally in a startup or high-growth company
- Based in or willing to commute to Chicago; in-person presence expected several days per week
- Exceptional organizational skills and a proactive, low-ego operating style
- Comfort with tools like Notion, Slack, Google Workspace, and Zoom
- Bonus: exposure to fintech, crypto, legal, or financial services environments
- Discretion is non-negotiable — you'll be handling sensitive business and investor information
Compensation: $85K–$115K base + equity
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