Location: Chicago, IL Headquarters
Type: Full-time, in office
Company Stage: Early-stage / startup
We’re a small, fast-moving team building something genuinely new. If you want real ownership, real impact, and the chance to build something from the ground up, keep reading.
About Us — Our Mission & Vision
At Autopilot, our mission is to free people up to do what they do best by automating everything else — building the infrastructure layer that powers autonomy in motion across the physical world. Our values are simple and non-negotiable: Do Good. Have Fun. Make Money.
Benefits
- Base Salary + Annual bonus potential
- 100% Employer-covered Health, Dental, and Vision Insurance
- 401(k) — Company-administered plan
- Flexible PTO
- Travel Reimbursement (where role-related travel is required)
- Team & Culture Events
The Role
We are looking for a Head of Operations to join our leadership team and own the internal engine of the company. You’ll sit at the leadership table, hold cross-functional accountability, and build 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 finance, people operations, recruiting, and internal operations while building the systems and team that scale beyond you.
Financial Planning & Business Operations
- Build and own 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
- Support investor relations and board materials — milestone tracking, operating metrics, KPI dashboards
- Partner with the CEO to make data-driven operating and investment decisions
People Operations — Full Function
- 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 integration, benefits syncing
- Payroll administration and benefits enrollment (health insurance, 401(k), and related programs)
- Contractor and 1099 management; employment classification decisions (W2 vs. contractor, FTE vs. part-time)
- Multi-state HR compliance — Illinois employment law, termination requirements, pay stub standards
- Culture infrastructure — 1:1 frameworks, performance review cycles, onboarding, team rituals
- Retention risk monitoring — spotting morale and capacity issues before they escalate
HR Compliance & Legal Risk Management
- 1099 tax filing accuracy and deadline management
- 401(k) integration and regulatory compliance
- Employment contract review, NDAs, and IP agreement management
- Coordination with outside legal and HR counsel when needed
- Build and maintain an HR compliance calendar — deadlines, filings, renewals
Vendor & Supply Chain Oversight
- Manage OEM vendor relationships — procurement, lead times, credit terms, and escalation protocols
- Build and enforce vendor SLAs — hold partners accountable to delivery and quality commitments
- Manage the company’s tools and software stack — evaluate, onboard, and sunset tools as needed
- Coordinate with the robotics field ops team on deployment readiness, site logistics, and inbound hardware logistics (freight, inventory tracking, fulfillment accuracy)
What We’re Looking For
- Thrive under pressure — early-stage startup pace motivates you
- Highly organized with a multiplier mindset — you prioritize the work that moves the top line
Required
- 8–12+ years in operations, people operations, finance, or a combination — ideally in a startup or high-growth environment
- A dual-track background spanning both people ops and finance
- Proven track record of building a people function from scratch — not inheriting one
- Direct experience managing payroll, benefits, and employment compliance
- Strong financial literacy — comfortable reading a P&L, building a budget, and tracking unit economics
- Experience as a member of or direct partner to a leadership team
- High ownership mindset and excellent written and verbal communication
Nice to Have
- Experience supporting a CEO through a fundraising process — board prep, investor materials, milestone tracking
- Exposure to hardware, logistics, or field operations businesses
- Familiarity with Rippling, Ramp, HubSpot, and Asana
- Experience managing fractional or outsourced financial services