Founding Head of Operations & Systems — Scale With Impact

AUTOPILOT; Chicago (IL); On-site; USD 100,000 - 200,000; Full time

Benefits offered by this job

Health insurance

Stock options

401(k) plan

Flexible PTO

Travel reimbursement

Team events

Job summary

AUTOPILOT is seeking a Founding Head of Operations & Systems to own the internal engine of our Chicago-based startup. You’ll sit at the leadership table, build finance, people ops, and operational infrastructure, and scale the company with high ownership and data-driven decisions.

You will personally lead finance, recruiting, payroll, HR compliance, and vendor management while shaping processes that support rapid growth and cross-functional alignment across a lean, fast-moving team.

Qualifications

• 8–12+ years of experience in operations, people operations, finance, or a mix — startup or high-growth
• Proven ability to build people functions from scratch and manage payroll, benefits, and compliance
• Strong financial literacy, P&L understanding, budgeting, and unit economics

Responsibilities

• Build and own operating budget by department, function, and quarter
• Forecast cash flow, burn rate, scenarios, and investor updates
• Own HR: recruiting, onboarding, compliance, payroll, benefits, and multi-state requirements
• Manage vendor relationships, tools, and procurement, optimizing spend and efficiency

Skills

Startup experience

Financial acumen

People operations

Cross-functional leadership

Communication

Tools

Rippling

Ramp

HubSpot

Asana

Job description

AUTOPILOT is seeking a Founding Head of Operations & Systems to own the internal engine of our Chicago-based startup. You’ll sit at the leadership table, build finance, people ops, and operational infrastructure, and scale the company with high ownership and data-driven decisions.

You will personally lead finance, recruiting, payroll, HR compliance, and vendor management while shaping processes that support rapid growth and cross-functional alignment across a lean, fast-moving team.