Founding Head of Marketing

Chicago, IL (On-site)

$120K/yr – $200K/yrSenior LevelFull time

Posted 13 hrs ago

Job Summary

Own the story and pipeline for Autopilot by defining messaging, building case studies, and leading the marketing function while scaling with a demand-gen and content team.

  • Own storytelling across verticals to drive pipeline
  • Build a library of customer proof and deployment outcomes
  • Stand up and scale the marketing organization and demand-gen engine

Job Description

Responsibilities

  • 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.
  • 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)

Requirements

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

Preferred

  • 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.

Benefits

  • Base Salary + Annual bonus potential
  • 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.
AUTOPILOT logo

AUTOPILOT

Autopilot is a next-gen trading app and registered investment advisor (RIA) that makes professional-style investing accessible to everyone. Users can autopilot the portfolios of politicians, public figures, and top investors, or create and launch their own fund for others to follow. Built for transparency and ease of use, Autopilot reimagines how people invest, manage, and grow their money.Backed by notable investors such as Craft Ventures (Airbnb, Slack, Tesla), Nomad Ventures (Intro, Bezel), Balaji Ventures (Perplexity), and Next Fund (7Signal).Autopilot is ranked among the Top 30 Most Downloaded Finance Apps. With over 3M+ million downloads, $1B+ in assets under management (AUM), 165k+ users, and a rapidly growing community of 90k+ subscribers, Autopilot is quickly becoming a leader in fintech.Autopilot Advisors, LLC is a registered investment adviser with the U.S. Securities and Exchange Commission (SEC). This page is intended for informational purposes only and does not constitute an offer to sell or a solicitation of an offer to purchase any securities or investment products. Any information contained herein is provided with the understanding that the recipient will conduct their own due diligence before making any investment decisions. Investments carry a risk of loss and past performance is not indicative of future results.

Founded in 2020
Los Angeles, California, USA
47 employees (6 in marketing)

Salaries

Posted range

$120K/yr – $200K/yr

Taken straight from the job posting.

The middle of this range ($160K) is 10% below the median base salary for Head of Marketing roles in the United States ($178K).

Head of Marketing median pay in the United States

$183K/yr

Most pay falls between $145K and $215K. Based on 133 salaries.

See all AUTOPILOT salaries

Marketing Team

Marketing Team Size
3 (6% of company)
Median Career Experience
8 years
Median Tenure
1.1 years
Marketing Roles Posted (Last 30 Days)
2

Funding

Total Funding
$19.6M
Last Raise
$8M
Undisclosed, 4 months ago

Funding History

  • Nov 2025
    Undisclosed • $8M
  • Nov 2024
    Undisclosed • $6.7M
  • Mar 2023
    Seed • $1.4M

Traffic Signals

Monthly Visitors
127K
Monthly Google Ads Budget
$5.8K
Traffic Source Mix
Search
34%
Direct
54.1%
Referral
5%
Social
6.3%
Paid
0.4%

Headcount Trend

Current headcount: ~47
AUTOPILOT logo

Founding Head of Marketing

AUTOPILOT · Chicago, IL · On-site