Executive Assistant

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