Founding Head of Operations & Systems

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. Founding Head of Operations & Systems 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. 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. 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 + Annual bonus potential The total compensation range for this role is $100,000-$200,000. This range reflects total target compensation, which includes base salary and bonus potential. Where a candidate falls within the range depends on factors such as experience and skills. Equity: Early-stage ownership through stock options. A chance to build meaningful value as we scale. 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. The Role We are looking for a Head of Operations & Systems 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. What You’ll Own 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. Financial Planning & Business Operations 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 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 — accuracy, cycle management, exceptions, and reconciliation Benefits enrollment and administration — health insurance, 401(k), and related programs Contractor and 1099 management — W9 collection, payment tracking, annual filings 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 buddy systems, team rituals, etc Retention risk monitoring — proactive identification of morale and capacity issues before they escalated 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 Building and maintaining 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 and site logistics Coordinate with the robotics field ops team on inbound logistics for hardware deployments — freight coordination, inventory tracking, fulfillment accuracy What We’re Looking For Thrive under pressure — early-stage startup pace doesn't rattle you, it motivates you. You've operated in environments where the priorities shift, the resources are lean, and the expectations are high Highly organized with a multiplier mindset — you instinctively prioritize the work that moves the top line, not just the work that fills the calendar Required 8–12+ years of experience 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 — you notice what's broken and fix it without being asked Excellent written and verbal communication — you can hold a room and hold people accountable 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 #J-18808-Ljbffr AUTOPILOT