Location
Chicago, IL Headquarters
Type
Full-time, in office
About Us - Our mission & vision
At Autopilot, our mission is to free people up to do what they do best by automating everything else. We are building the infrastructure layer that powers autonomy in motion across the physical world, including sports, fitness, logistics, healthcare, and more. Our systems help robots move, record, deliver, train, and connect in real-world environments that have historically lacked modern tooling. Our values are simple and non-negotiable: Do Good. Have Fun. Make Money. We believe these are mutually reinforcing, and we work hard to uphold them as we grow.
We move fast, operate scrappy, and care deeply about building something that works.
Benefits
You will be eligible to participate in company benefits and perks, which currently include:
- Base Salary: The base salary range for this role is $85,000-$120,000, depending on experience. Experienced candidates may also be eligible for a performance bonus.
- 100% Employer-covered Health, Dental, and Vision Insurance
- 401(k) - Company-administered plan
- Flexible PTO - Time off as needed, coordinated with your team
- 18 Paid Holidays
- Travel Reimbursement - Reimbursed in accordance with company policy, where role-related travel is required
- Team & Culture Events - Team offsites, social events, and company-sponsored activities
Benefits and policies may be updated from time to time at the company's discretion.
The role
We're looking for a Founder Associate who acts as the CEO's right hand and helps them show up at their best, inside the company and out. You'll run the CEO's calendar, inbox and travel, manage their personal content calendar, look for ways to grow their visibility, and organize the dinners and meetings where relationships with customers, partners, and investors get built. You'll also build AI agents and automations that take repetitive work off the CEO's plate. You'll be trusted with sensitive information, including fundraising, board matters, and people decisions, and you'll treat it with complete discretion.
This role is a great fit if you come from sales, marketing, or content creation at a startup, or if you're ready to move into tech and want a front-row seat to how a venture-backed company operates.
A day in the life
Your morning starts before the CEO's does. You send a short brief covering the day's meetings, who they're meeting and why it matters, and anything that changed overnight. You've already moved a conflict, confirmed a car to the airport, and flagged two emails that need the CEO's answer.
Mid-morning, the two of you spend 15 minutes on the content calendar. You've drafted a LinkedIn post from last week's customer visit and pulled together a few ideas for raising the CEO's profile, like a podcast that fits our market or a panel at an upcoming robotics conference.
In the afternoon, you're planning a dinner for an investor and two partners who are in town next week: the restaurant, the guest list, the briefing notes, and the follow-up. In between, you're improving an AI agent you built that drafts meeting prep from the CEO's calendar and inbox, so next week's briefs take half the time.
By the end of the day, action items from the CEO's meetings are captured and assigned, tomorrow is set, and nothing is waiting on the CEO that doesn't need to be. Some days that also means handling a personal errand or booking a personal trip, because work and life overlap for a founder. Every day, you're learning how a venture-backed tech company actually runs.
What you'll own
CEO Office & Calendar
- Run the CEO's calendar, inbox, and daily priorities, and act as the first point of contact for people trying to reach them
- Send a daily brief and weekly preview, and keep the CEO's top priorities and key projects current
- Prepare briefing materials and research for meetings, capture action items and follow up until they're closed
- Draft announcements, investor updates, and presentations, and route documents that need the CEO's signature
- On occasion, attend meetings on the CEO's behalf and report back
- Submit business expense reports and schedule CEO interviews for open roles with our Operations team
Personal Brand & Visibility
- Manage the CEO's personal content calendar across LinkedIn and other channels
- Draft and schedule posts and other content for the CEO's approval, and keep their voice consistent
- Find ways to grow the CEO's visibility, including podcasts, panels, events, and press opportunities
Travel, Events & Relationships
- Coordinate business travel and events, including multi-city trips, visas, and backup plans when things change
- Organize high-profile dinners and meetings with customers, partners, and investors, from invites to follow-up
- Host board members, investors, and customers at HQ, and keep key relationships warm with thank-yous, gifts, and check-ins
- Coordinate board meetings and support investor updates, fundraising meetings, and data room organization
- Lend a hand on in-house events when our Operations team asks
AI & Automation
- Build AI agents and automations that take repetitive work off the CEO's plate, such as meeting prep, inbox triage, and follow-ups
- Set up systems in Google Workspace, Notion, and Asana that keep the CEO's work organized and visible
- Document how the CEO's office runs so it can scale as the company grows
Personal Support (a few hours a week)
- Manage the CEO's personal calendar, appointments, errands, and personal travel
- Keep personal and company spending separate, with personal items on the CEO's own card
What success looks like
- The CEO's time goes to the highest-priority work, with fewer conflicts and wasted meetings
- The CEO walks into every meeting prepared, and nothing falls through the cracks after it
- The CEO's content goes out on schedule, and their visibility grows quarter over quarter
- High-profile dinners and meetings run smoothly and lead to clear next steps
- The AI agents you build save the CEO real time every week
- Board, investor, and people information is handled with complete discretion
What we're looking for
You're organized and on point
- You're detail-oriented and catch small mistakes before they turn into big ones
- You're on time and prepared, and you keep track of every commitment
- You think a step ahead and anticipate what the CEO needs before they ask
You communicate well and keep things confidential
- You write clearly and can write in someone else's voice, from a quick email to a LinkedIn post
- You're comfortable with board members, investors, customers, and partners
- You know when to act on your own and when to escalate
- You have the CEO's best interest in mind and handle sensitive information with complete discretion
You're curious about tech and AI
- You use tools like Claude, ChatGPT, or similar every day and like figuring out how to make them do more
- You've built simple agents or automations, or you're excited to learn fast
- You want to understand how a venture-backed tech company is built, funded, and run
You thrive in a startup environment
- You stay calm when plans change at the last minute
- You enjoy working in person with a small team where priorities evolve and individual contributions matter
Experience
- 2-5 years in a fast-paced role at a startup or high-growth company, such as sales, marketing, content creation, operations, or executive support
- Experience creating content or managing social media, for yourself or for a brand, is a plus
- 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
- Regular evening and weekend availability, mostly async or remote
- Interest in robotics, automation, or technology
- Ability to work onsite at our Chicago headquarters
Apply
Submit your resume and LinkedIn profile, along with a brief note about why you want to work side by side with a startup CEO. Bonus points for a link to content you've created or something you've automated.
Autopilot is an equal opportunity employer. We welcome applicants of all backgrounds. If you need an accommodation to apply, contact takeoff@operationautopilot.com.
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