Head of Operations & Systems

Head of Operations & Systems Location

Chicago, IL Headquarters

Full-time, in office

Early-stage / startup

We're a small, fast-moving team building something genuinely new. The right person for this position is highly organized, naturally prioritizes the work that moves the top line, and doesn't need a fully built playbook to get started. Early-stage startup life means shifting priorities, lean resources, and high expectations, and that energizes you rather than slows you down. If you're looking for a structured corporate environment with defined processes and a large support team, this probably isn't the right fit.

If you want real ownership, real impact, and the chance to build something from the ground up, keep reading.

• 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.

You will be eligible to participate in company benefits and perks, which currently include:

• Base Salary + Annual bonus potential
• 100% Employer-covered Health, Dental, and Vision Insurance
• 401(k)

• Company-administered plan
• Flexible PTO
• Time off as needed, coordinated with your team
• 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.

We are looking for a Head of Operations.

to join our leadership team and own the internal engine of the company. This person will sit at the leadership table, hold cross-functional accountability, and be responsible for building the people, financial, and operational infrastructure that allows Autopilot to scale..

The right candidate has done this before — built people functions from scratch, navigated compliance in a fast-moving environment, held a P&L, and knows what it takes to run a company operationally.

This is a true player-coach role. In the beginning, you'll personally own much of the company's finance, people operations, recruiting, and internal operations while building the systems and team that will eventually scale beyond you.

You will be managing internal systems, day to day program management, and embedding AI into all aspects of our business — ensuring the right processes, documents, knowledge, and systems are in place to drive faster operating cadences and exceeding company goals.

• Building and owning an operating budget — by department, by function, by quarter
• Financial forecasting — cash flow visibility, burn rate, and scenario planning
• Unit economics tracking — cost per deployment, cost per subscription, gross margin by customer
• Vendor and spend management — invoice approval, corporate card reconciliation, cost optimization
• Monthly financial reporting in partnership with external bookkeeping support
• Evaluating and managing fractional financial services for value and fit
• Supporting investor relations — milestone tracking, operating metrics reporting, investor update preparation
• Supporting board materials — financial summaries, KPI dashboards, and operational highlights
• Partner with the CEO to make data-driven operating and investment decisions

• Full-cycle recruiting across all open roles — sourcing, screening, scheduling, offer management
• Role definition and job architecture in partnership with department leads and the CEO
• Onboarding and offboarding — from offer letter to system access to exit interview
• Rippling administration — org chart, employee records, payroll…