Founding Demand Generation / Growth Marketer

Trailmate (Seed Stage LegalTech AI Startup)

  • Location: Remote (U.S. preferred)
  • Type: Full-time
  • Compensation: Competitive salary + equity

About Us

Trailmate is the first AI-native teammate for law firms. We help plaintiff-side attorneys transform client intake, discovery, and case management through structured AI workflows that make firms faster, leaner, and more client-friendly.

To fuel growth, we’re hiring a Founding Demand Generation / Growth Marketer who can own campaigns, test channels, and build a predictable pipeline.

What You’ll Do

  • Build and execute multi-channel demand gen campaigns (paid, organic, events, email, LinkedIn).
  • Own top-of-funnel lead generation: identify what drives awareness and demo requests.
  • Develop and optimize landing pages, nurture flows, and marketing automation.
  • Partner with the AE/SDR team on outbound campaigns and sales enablement.
  • Drive Trailmate’s event strategy: state bar conferences, legaltech expos, webinars.
  • Track campaign ROI and attribution, double down on what works.
  • Build early brand awareness in legaltech through creative, scrappy growth experiments.

What We’re Looking For

  • 3–6 years of demand generation or growth marketing experience (B2B SaaS preferred).
  • Hands-on experience running paid campaigns, marketing automation, and funnel analytics.
  • Strong content instincts—you know how to make collateral that converts.
  • Comfortable wearing multiple hats (from running ads to drafting email copy to testing LinkedIn campaigns).
  • Analytical and experimental: you move fast, measure everything, and iterate.
  • Bonus: experience marketing into professional services or legaltech.

Why Join Us

  • Impact: As our first growth hire, you’ll build the demand gen engine from scratch.
  • Category Creation: AI is reshaping legaltech—you’ll own the campaigns that position Trailmate as the category leader.
  • Upside: Competitive salary + equity. Early hires share in the upside.
  • Growth Path: Opportunity to scale into Head of Growth or Marketing leadership as we expand.

Join Us on the Ground Floor

We're building something ambitious at the intersection of law and AI. If you're excited about shaping the future of legal technology and want to make an outsized impact from day one, explore our open roles below and let's talk.