CEO Office Chief of Staff (Founder Associate)

AUTOPILOT; Chicago (IL); On-site; USD 85,000 - 120,000; Full time

Benefits offered by this job

Base Salary: $85,000-$120,000, DOE

Health, Dental, Vision Insurance

401(k) – Company-administered plan

Flexible PTO

18 Paid Holidays

Travel Reimbursement

Team & Culture Events

Job summary

Autopilot, a Chicago-based startup, seeks a Founder Associate to work closely with the CEO, managing calendars, travel, and personal content while shaping the CEO’s visibility and company operations.

You will build AI agents and automations, coordinate high-profile dinners and investor meetings, and ensure discreet handling of sensitive information in a fast-paced venture-backed environment.

Qualifications

• 2-5 years in a fast-paced role at a startup or high-growth company (sales, marketing, content creation, operations or executive support).
• Experience creating content or managing social media is a plus.
• Experience supporting an executive, board or investors is a plus.
• Strong with Google Workspace and Slack; Notion and Asana are a plus.
• Regular evening and weekend availability, mostly async or in-person as needed.
• Interest in robotics, automation or technology.
• Ability to work onsite at our Chicago headquarters.

Responsibilities

• Run the CEO’s calendar, inbox and daily priorities; act as first contact point.
• Send daily briefs and weekly previews; track top priorities and projects.
• Prepare briefing materials and research; capture and close action items.
• Draft announcements, investor updates and presentations for signature routing.
• Attend meetings on the CEO’s behalf when needed and report back.
• Submit expense reports and schedule CEO interviews with the Operations team.
• Build AI agents and automations to reduce repetitive work.
• Set up systems in Google Workspace, Notion and Asana; keep work organized.
• Document how the CEO’s office runs to scale with the company.

Skills

Organizational Skills

Communication

Confidentiality

Tech & AI interest

Startup experience

Tools

Google Workspace

Slack

Notion

Asana

Job description

Autopilot, a Chicago-based startup, seeks a Founder Associate to work closely with the CEO, managing calendars, travel, and personal content while shaping the CEO’s visibility and company operations.

You will build AI agents and automations, coordinate high-profile dinners and investor meetings, and ensure discreet handling of sensitive information in a fast-paced venture-backed environment.