Founding Customer Success Manager / Implementations Lead Trailmate (Seed Stage LegalTech AI Startup)

WP Engine, Inc.; Tulsa (OK); Remote; USD 85,000 - 125,000; Full time

Job summary

Trailmate is seeking a Founding Customer Success Manager / Implementations Lead to be the face of the company for customers, guiding implementation and adoption of our AI-enabled legal workflows.

You will own onboarding, drive post-sale success, and build repeatable playbooks while collaborating with sales to ensure smooth handoffs from closed deals to happy customers. Remote-first role with US focus.

Qualifications

• 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.

Responsibilities

• 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).

Skills

Customer success

Onboarding

SaaS

Account management

Training

Communication

Empathy

Entrepreneurial mindset

Job description

Founding Customer Success Manager / Implementations Lead

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.