Founder Associate — AI-Driven CEO Office Partner (Chicago)

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

Benefits offered by this job

Salary range

Health insurance

401(k)

Flexible PTO

Holidays

Travel reimbursement

Team events

Job summary

Autopilot is seeking a Founder Associate to work directly with the CEO in Chicago. You will manage the CEO's calendar, inbox, travel, and personal content calendar, and help raise the CEO's visibility through posts, podcasts, and events.

You will also build AI agents to automate routine tasks. This venture-backed startup role is hands-on, fast-paced, and offers exposure to fundraising, board matters, and key partnerships as it grows from its early stages.

Qualifications

• 2–5 years in a fast-paced startup or high-growth role.
• Experience supporting an executive, board or investors is a plus
• Strong with Google Workspace (Gmail, Calendar, Drive) and Slack; familiarity with Notion and Asana is a plus

Responsibilities

• Manage the CEO's calendar, inbox and daily priorities.
• Prepare briefing materials and research for meetings; capture action items.
• Draft announcements, investor updates and presentations; route documents.
• Plan and coordinate travel, events and dinners with customers, partners and investors.
• Build AI agents and automations to reduce repetitive work for the CEO.

Skills

Organizational skills

Communication skills

Attention to detail

Discretion

Tools

Google Workspace

Slack

Notion

Asana

Job description

Autopilot is seeking a Founder Associate to work directly with the CEO in Chicago. You will manage the CEO's calendar, inbox, travel, and personal content calendar, and help raise the CEO's visibility through posts, podcasts, and events.

You will also build AI agents to automate routine tasks. This venture-backed startup role is hands-on, fast-paced, and offers exposure to fundraising, board matters, and key partnerships as it grows from its early stages.