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're looking for a business-savvy technical builder who designs, owns, and operates the systems that power Autopilot's entire revenue motion. You'll maintain and extend our AI-powered email automation infrastructure, build trigger-based outbound flows that run without human intervention, own HubSpot as a data system (not just a tool), and ensure clean, reliable data moves across every connected platform. When something breaks, you find it before the team does. When a new motion needs to be built, you architect it from the ground up — enrichment pipelines, ICP scoring, lead routing logic, sequence triggers, and the attribution models that tell leadership what's actually working. This is an infrastructure-first role where the output isn't a report or a recommendation — it's a running system that generates and converts pipeline.
What You'll Own
AI Workflows & Automation Infrastructure
- Maintain and extend the API email automation system — prompt logic, template deployment, workflow triggers, and failure handling
- Build AI-powered workflows for personalization, lead enrichment, scoring, and outreach sequencing
- Own uptime and reliability of automation systems — if something breaks, you find it before the team does
- Document every system you build so it can be understood, extended, or handed off
Prospecting Systems & Outbound Infrastructure
- Own the technical architecture of the outbound motion — enrichment pipelines, ICP scoring, list building logic, and sequence triggers
- Build trigger-based outbound flows: lead hits a status in HubSpot → enrichment fires → personalized sequence launches — with no human in the middle
- Manage email deliverability infrastructure — domain health, sending warmup, inbox placement, and bounce handling
CRM Architecture & Data Infrastructure
- Own HubSpot as a data system — not just a tool. That means lifecycle stage definitions, custom properties, pipeline logic, workflow architecture, and data integrity
- Maintain clean, reliable data flow between all connected tools and tech stack
- Build and maintain lead routing, scoring, and sales handoff logic — including the triggers that move leads between marketing and sales ownership
Attribution & Revenue Reporting
- Own attribution — multi-touch models that accurately credit which channels, campaigns, and touchpoints drive pipeline and closed revenue
- Deploy and maintain GTM and tracking across all landing pages and funnels — clean event data from ad click to meeting booked
- Build dashboards that give leadership real visibility into funnel health, CAC, pipeline velocity, and campaign ROI
What We're Looking For
You build, you don't just configure
- You've connected tools via APIs and webhooks without filing a ticket to a software engineering team
- You think in systems: inputs, outputs, failure modes, and edge cases — not just happy-path flows
You understand the revenue context
- You know the difference between an MQL and an SQL — and you design systems that respect that distinction
- You can name the pipeline impact of a workflow improvement, not just describe it.
- You've shipped automations that measurably increased meetings booked, reply rates, or pipeline velocity — and you can prove it
You're fluent in the modern GTM stack
- HubSpot: custom objects, workflow logic, lifecycle stages, API integration — not just the UI
- Clay or equivalent: enrichment pipelines, ICP scoring, waterfall logic, and multi-source enrichment
- LLM APIs (Claude and/or OpenAI): using them as workflow components, not chat interfaces
- No-code automation: Make, n8n, or Zapier for rapid workflow prototyping
- GTM / GA4: front-end event tracking, funnel instrumentation, and attribution configuration
Experience
- 4–10 years in a GTM engineering, marketing ops, revenue ops, or technical growth role
- Demonstrated track record of shipping automations with documented, measurable pipeline outcomes
- Experience in a startup or fast-moving environment — you've built without perfect specs and shipped anyway
- Python or JavaScript fluency — you don't need to be a software engineer, but you can write and debug a production script
- AI tooling experience (Claude API, OpenAI, or equivalent) as part of a real workflow — not just experimentation