Careers at Trailmate

Join the company shaping the future of the legal industry—built by a culture of excellence and supported by a team redefining what’s possible.
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Join at the Ground Floor

Trailmate is early—but real. The product is live, in use, and evolving quickly with real law firms and real clients. Joining now means:

Direct ownership

over meaningful product areas

Real influence

on architecture, UX, and strategy

Fast iteration

with immediate feedback from production use

Category-defining work,

not incremental features

There is no bureaucracy here yet. No legacy decisions to tiptoe around. You will help define not only what we build, but how this company operates.

If you want to look back in a few years and say

“I helped build that from the beginning,”

this is that moment.

What Our Team Has To Say

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“At Trailmate, every project feels like a chance to innovate at the edge, backed by a team that’s as driven as I am. I truly believe we’re not just building technology—we’re reshaping an entire industry.”

Jameson Moyer

Founding Account Executive

“If you join Trailmate, your work will matter from day one. We see a clear future for how work gets done within law firms—and we’re excited to build it.”

Manny Starr

Founder

“This team combines technical depth with a real understanding of how law firms actually operate. That’s what makes it possible to build something truly transformative for the legal industry.”

Vipul Nandan

CTO

Interested in working at Trailmate?

Apply to join the team and help define what the next generation of legal AI looks like.

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.

We're hiring

Founding Product Marketing Manager Trailmate (Seed Stage LegalTech AI Startup) Founding Customer Success Manager / Implementations Lead Trailmate (Seed Stage LegalTech AI Startup) Founding Demand Generation / Growth Marketer Trailmate (Seed Stage LegalTech AI Startup) Founding Sales Development Representative (SDR) Trailmate (Seed Stage LegalTech AI Startup)