Founding Head of GTM & Demand Gen

Chicago, IL (On-site)

$100K/yr – $200K/yrSenior Level7+ years expFull time

Posted 2 weeks ago

Job Summary

Own the GTM strategy and demand gen across enterprise and partners, drive pipeline with hands-on execution, and build scalable systems for growth.

  • Lead campaigns across paid, email, SEO, and content
  • Own HubSpot automation and reporting

Job Description

Responsibilities

  • Go-to-Market Strategy & Growth - Own our GTM strategy and demand generation roadmap across enterprise and channel partners.
  • Identify new growth opportunities, verticals, and acquisition channels.
  • Partner with Sales, Product and Leadership to drive pipeline and revenue.
  • Demand Generation & Marketing Execution - Personally build and optimize campaigns across paid media, email, SEO/GEO, content, events, and emerging channels.
  • Own HubSpot marketing automation, lifecycle campaigns, and reporting.
  • Manage agencies, vendors, and AI-powered marketing tools to maximize performance.
  • Continuously test, learn, and improve marketing performance across every channel.
  • Content, Analytics & Operations - Own messaging, positioning, content strategy, and organic growth.
  • Build dashboards that measure pipeline, conversion, and marketing ROI.
  • Present actionable insights and recommendations to leadership.

Requirements

  • 7+ years building demand generation or growth programs in B2B SaaS or technology.
  • Experience at an early-stage or high-growth company where you’ve built programs from scratch.
  • Demonstrated success generating measurable pipeline and revenue growth.
  • Experience owning strategy while remaining hands-on in execution.
  • Bias toward action. You'd rather launch, measure, and improve than spend weeks perfecting a plan.
  • You’re a builder.
  • You've built and executed demand generation programs yourself – not just managed agencies or approved strategy.
  • You're equally comfortable developing a GTM plan and launching a campaign in HubSpot that same day.
  • You thrive in early-stage environments where ownership is high and playbooks don't exist yet.
  • You're resourceful. You know how to deliver results without a large budget or a large team.

Benefits

  • 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
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

$100K/yr – $200K/yr

Taken straight from the job posting.

See all AUTOPILOT salaries

Marketing Team

Marketing Team Size
3 (6% of company)
Median Career Experience
8 years
Median Tenure
0.9 years
Marketing Roles Posted (Last 30 Days)
1

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

Recent News

AUTOPILOT logo

Founding Head of GTM & Demand Gen

AUTOPILOT · Chicago, IL · On-site