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 is highly organized, naturally prioritizes the work that moves the top line, and doesn’t need a fully built playbook to get started. 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 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’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, and ensure clean, reliable data across every connected platform. The output isn’t a report or a recommendation — it’s a running system that generates and converts pipeline.
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: 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 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 an 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 design systems that respect that distinction
- You’ve shipped automations that measurably increased meetings booked, reply rates, or pipeline velocity — and you can prove it
- Fluent in the modern GTM stack: HubSpot (custom objects, workflows, lifecycle stages, API), Clay or equivalent (enrichment, ICP scoring, waterfall logic), LLM APIs (Claude and/or OpenAI) as workflow components, no-code automation (Make, n8n, or Zapier), and GTM / GA4
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 can write and debug a production script
- AI tooling experience (Claude API, OpenAI, or equivalent) as part of a real workflow — not just experimentation