Trailmate (Seed Stage LegalTech AI Startup)
- Location: Remote (U.S. preferred)
- Type: Full-time
- Compensation: Competitive base + commission + equity
About Us
Trailmate is reimagining how law firms work. Our AI-native platform acts as a true teammate for attorneys and staff, automating client intake, discovery, and communication in ways no client portal ever has.
We’re looking for a Founding SDR to generate pipeline, experiment with outreach strategies, and partner closely with the founder and our first AE. If you’re scrappy, competitive, and excited by AI, this is the role for you.
What You’ll Do
- Prospect into plaintiff-side law firms and other high-value targets.
- Research accounts, identify decision makers, and craft personalized outreach.
- Run outbound campaigns (email, LinkedIn, events, phone).
- Qualify inbound leads and set meetings for the AE/founder.
- Track and report on outreach performance to improve conversion.
- Be creative—test scripts, cadences, and messaging that become our future playbook.
What We’re Looking For
- 0–3 years of experience in a sales or business development role (SaaS/tech is a plus).
- Tenacious prospector who isn’t afraid of cold outreach.
- Strong written/verbal communication skills.
- Self-starter who thrives in early-stage ambiguity.
- Curiosity about AI and how it’s reshaping industries.
- Desire to grow into a closing role (AE path).
Why Join Us
- Career Acceleration: Founding SDR → AE track as we scale.
- Equity: Ownership in a venture-backed company at the start of its growth curve.
- Category Creation: Be part of the first AI-native platform for law firms.
- Team: Work directly with the founder and first AE to shape GTM from scratch.
