Founding Head of Marketing at Autopilot in Chicago

Location: Chicago, IL Headquarters or San Francisco, CA or New York, NY

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, skills, and locations.
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
Own how Autopilot tells its story and turns that story into pipeline. You'll set messaging, positioning, and go-to-market narrative across our verticals, build the customer-proof library that closes enterprise deals, and stand up the marketing function. Starting as a player-coach who writes the case study and sets the strategy, then hiring the demand-gen and content execution beneath you as we scale.

What You'll Own
GTM Strategy & Positioning

Own messaging, positioning, and value proposition across enterprise and channel, tailored by vertical and by buyer.

Partner with Sales, Product, and Leadership to translate company strategy into a marketing plan that drives pipeline.

Develop sales plays and enablement - battle cards, objection handling, one-pagers to close the sales-process gaps surfaced in win/loss analysis.

Storytelling & Customer Proof
Build Autopilot's library of case studies, ROI documentation, and deployment outcomes end-to-end. The proof assets are critical to converting enterprise pilots.

Develop thought leadership that positions Autopilot as a serious player in facility automation, speaking the language of enterprise buyers.

Coordinate with Customer Success and Sales to surface the strongest stories and access the right contacts.

Demand Gen &; Marketing Operations (build & oversee)
Own the demand-gen roadmap and stand up the engine: HubSpot marketing automation, lifecycle campaigns, paid media, SEO/content, and reporting. Personally at first, then through new hires and/or agencies.
Build dashboards for pipeline, conversion, and marketing ROI; present actionable insights to leadership.
Brand, Content & Events
Maintain brand consistency across all channels; own the editorial calendar and content that feeds paid, email, and SEO.
Own Autopilot's presence at trade shows and live demo events, from planning through post-event nurture.

Team Building
Hire and develop the marketing org — starting with a demand-gen operator to complement your strategy-and-content strength.

You're ambitious and career-oriented
You're not here for a maintenance job. You see this as a place to build something and grow with it
You understand that content at a startup isn't just blog posts — it's sales ammo, brand positioning, and customer trust

Wired for speed — you make decisions with imperfect information, ship work, and iterate rather than waiting for everything to be perfect

Highly organized with a multiplier mindset — you instinctively prioritize the work that moves the top line, not just the work that fills the calendar

Experience
5–10 years in content marketing, brand, events, or a marketing generalist role with a demonstrated content focus

HubSpot proficient — you know your way around campaigns, lists, workflows, and reporting without needing a tutorial

Startup or early-stage company experience strongly preferred — you've built without a large team or a big budget

AI-native in your day-to-day — you default to tools like Claude, ChatGPT, or similar to move faster, write better, and solve problems before asking for help