Trailmate (Seed Stage LegalTech AI Startup)
- Location: Remote (U.S. preferred)
- Type: Full-time
- Compensation: Competitive base + uncapped commission + meaningful equity
About Us
Trailmate is building the first AI-native teammate for law firms. Our product is already in the hands of design partners and automates high-value workflows like client intake, discovery, and settlement coordination.
This is not “just another SaaS sales role.” We’re creating a new category at the intersection of AI + legal services, and we’re looking for a founding Account Executive who wants to own pipeline, close deals, and help shape how law firms adopt AI.
What You’ll Do
- Run the full sales cycle: prospect → demo → pilot → close.
- Work directly with the founder to refine messaging, pricing, and GTM strategy.
- Partner with customer success to ensure smooth implementations.
- Travel to key conferences and bar association events to build pipeline.
- Create repeatable sales playbooks that future reps will use.
- Be the voice of the customer—bring market feedback into product, marketing, and leadership conversations.
What We’re Looking For
- 3–6 years of closing experience in SaaS (startup or legaltech preferred).
- Strong track record of hitting/exceeding quotas.
- Comfort selling into professional services firms (bonus if you’ve sold to law firms).
- Entrepreneurial mindset: you thrive on ambiguity, hustle, and experimentation.
- Excellent communication skills—equally persuasive on Zoom, at events, or in-person with firm partners.
- Desire to be an early team member and shape a company from the ground up.
Why Join Us
- Impact: You’ll be our first AE. Your work directly sets the revenue trajectory of the company.
- Upside: Competitive OTE + equity package; early hires share in the upside of building something huge.
- Category Creation: Legaltech is a $50B+ industry, and we’re at the front edge of the AI transformation.
- Speed: We move fast—ship quickly, sell aggressively, and celebrate wins together.
