Trailmate (Seed Stage LegalTech AI Startup)
- Location: Remote (U.S. preferred)
- Type: Full-time
- Compensation: Competitive salary + bonus + equity
About Us
Trailmate is building the first AI-native teammate for law firms, transforming how attorneys and staff run cases. Our product already automates client intake, discovery, and communication in ways that make law firms faster, leaner, and more client-friendly.
To make our law firm customers successful, we’re hiring our first Customer Success Manager / Implementations Lead. This is not a back-office role—you’ll be the face of Trailmate for our customers, helping them deploy AI into mission-critical workflows.
What You’ll Do
- Lead new customer onboarding: map firm workflows → configure templates → train staff.
- Own post-sale success: drive adoption, satisfaction, and renewals.
- Build repeatable playbooks for onboarding, training, and account growth.
- Partner with sales to ensure smooth handoff from “closed deal” to “happy customer.”
- Serve as the customer’s voice: capture feedback and translate it into product requirements.
- Become an expert in legal workflows (employment, PI, consumer law) to guide customers effectively.
- Experiment: test new ways to drive engagement (automated check-ins, playbooks, webinars).
What We’re Looking For
- 3–6 years in customer success, implementations, or account management (SaaS experience required).
- Strong track record of managing onboarding and retention for SMB/mid-market clients.
- Bonus: experience with legaltech, legal operations, or professional services firms.
- Excellent communication and training skills—you know how to make customers feel supported and confident.
- Entrepreneurial mindset: you enjoy building processes, not just running them.
- Empathy + hustle: you’ll be helping lawyers adopt AI—patience and persistence required.
Why Join Us
- Impact: You’ll be the first CSM and shape how every law firm uses Trailmate.
- Growth: Opportunity to build and lead a team as we scale.
- Upside: Competitive pay + equity—early hires share in the upside.
- Category Creation: Join the first AI-native client platform for law firms, at the start of a legal industry transformation.
