Founding Customer Success Lead - Implementations

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

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.