Executive Assistant

Found AI; Chicago (IL); Hybrid; USD 80,000 - 95,000; Full time

Benefits offered by this job

Medical (BCBSIL Blue PPO)

Dental (75% company-paid)

Vision coverage (voluntary)

Unlimited PTO

Job summary

Found AI is seeking an experienced executive assistant to support the Founder & CEO in Chicago, hybrid work. You will own the CEO's calendar, handle travel and expenses, and ensure the office runs smoothly.

The role requires 5+ years supporting senior executives, strong written communication, and proactive autonomy to keep the CEO focused on customers, candidates, and investors.

Qualifications

• Supported a founder or C-suite executive with calendar management and strategic prioritization.
• Demonstrated discretion handling sensitive information (comp, board discussions).
• Clear written communication and independent decision-making when supporting executives.

Responsibilities

• Own the CEO's calendar end to end: scheduling, priorities, prep.
• Take travel, expenses, and follow-ups off the CEO's plate. Manage office logistics.
• Coordinate Chicago office operations and onboarding for new hires and events.

Skills

Executive support

Calendar management

Discretion

Email drafting

Travel logistics

Job description

Companies run on complex, invisible context, institutional knowledge that standard internal systems miss. Without this context, enterprise AI becomes an expensive generator of generic responses that fail to scale. Found captures your unique business context (your data, decisions, and frameworks) and builds it into a compounding Context Graph resulting in more accurate, secure and cost efficient intelligence. From this foundation, our Solutions Team deploys autonomous AI systems into key business functions to capture slipped value. Our success aligns with yours as we focus on outcomes generated, not seats or tokens. We're venture-backed, working with early design partners, and selling into the office of the CFO and CIO.

Why this role exists

Today the CEO runs his own calendar, travel, and follow-ups, and the office runs on whoever notices first. Every hour on logistics is an hour not spent with customers, candidates, or investors. This is the first executive-support seat: you own the CEO's time and keep the Chicago office running. Do this well and the CEO's week gets measurably bigger.

What you'll deliver

First 90 days

• Own the CEO's calendar end to end: scheduling, priorities, prep. No meeting starts without context.
• Take travel, expenses, and follow-ups off the CEO's plate entirely.
• The office runs without anyone asking: supplies, vendors, and the in-office days people plan around.

First 12 months

• The CEO spends measurably more time on customers, candidates, and product because you run everything else.
• Board meetings, offsites, and customer visits happen without a logistics miss.
• The office operating rhythm, from onsites to a new hire's first day, is a system anyone could follow.

What you'll own

• The CEO's time: calendar, priorities, and the judgment calls about what earns a slot.
• Meeting readiness: agendas, briefs, notes, and follow-ups that don't slip.
• CEO travel and expenses, end to end.
• Logistics for board meetings, investor sessions, and executive offsites.
• The Chicago office: space, vendors, supplies, and the three-day-a-week onsite experience.
• Team moments that land: a new hire's day one, events, celebrations.

Must-haves

• You've supported a founder or C-suite executive and run their calendar with real judgment about what matters, not just what's asked.
• You operate ahead of the person you support: you see the conflict, the missing prep, the unbooked flight before they do.
• You handle sensitive material (comp, deals, board conversations) with complete discretion.
• You write clearly enough to send email on the CEO's behalf without a rewrite.
• You tell the truth about what's slipping, including on your own plate.

Nice-to-haves

• Early-stage startup experience where you built the process instead of inheriting it.
• Fluency with modern productivity tools, including AI.

How we'll know you fit

• Trust: is earned and acts as the Foundation of every interaction.
• Childlike Curiosity: you learn perpetually, ask why, and meet the world with wonder.
• Abundance Mentality: you expand through collaboration and optimism. The only limits are the ones you accept.
• Proactive Autonomy: you think independently and take initiative without waiting for permission.
• Execute Relentlessly: you move with urgency and discipline, turning ideas into outcomes through obstacles.
• Intellectual Honesty: you pursue truth over ego, challenge ideas rigorously, and adapt to new evidence.
• Collective Accountability: you share responsibility for the quality and impact of what we build together.

Logistics

Location: Chicago, hybrid. In office three days a week.

Reports to: Founder & CEO

Experience: 5+ years supporting senior executives

Salary Range: $80,000 - $95,000; the candidate qualifications will determine ultimate compensation.

Benefits: Medical (BCBSIL Blue PPO, 90% company-paid), dental (75% company-paid), voluntary vision coverage, unlimited PTO.

Type: Full-time

Equal opportunity

Found AI is an equal opportunity employer. We hire on evidence of the work and the values above, not pedigree. If you read the must-haves and you're close but not a perfect match, apply anyway and tell us why you'd be good at this. The calibration above means we'd rather assess than screen you out. We'll provide reasonable accommodation in the hiring process on request.