Remote Litigation AI Training Lead

Syllo; Oregon; Hybrid; USD 130,000 - 160,000; Full time

Benefits offered by this job

Equity in compensation

Benefits

Job summary

Syllo is seeking an AI Workflows Training Lead to own the content and delivery of all AI workflow training for internal teams and external clients. You will translate complex AI functionality into practical instruction for paralegals, attorneys, and legal ops professionals.

You will design the curriculum, deliver live and recorded sessions, and tailor enablement content to different user personas, while updating materials as the platform evolves.

Qualifications

• 3+ years of experience in litigation (JD preferred).
• Strong presentation skills and comfort presenting to mixed-expertise audiences, from legal technology directors to practicing attorneys.
• Experience with training, curriculum design, or technical enablement, with direct exposure to AI-powered tools or workflows.
• Experience training legal audiences (attorneys, paralegals, legal ops) is a strong plus.
• Ability to learn new software capabilities quickly and translate them into clear instructional content.
• Experience collaborating with product or engineering teams to track and interpret feature releases.
• Familiarity with LMS platforms, video production tools, and learning asset formats a plus.

Responsibilities

• Design, build, and maintain the AI workflows curriculum for both internal and external audiences.
• Deliver live training sessions and recorded modules covering Syllo's AI workflow features.
• Develop enablement content specifically suited for different user personas, accounting for differences in technical fluency, role responsibility, and daily workflow.
• Regularly update training materials to align with Syllo platform updates.
• Collaborate with the Instructional Designer on the production of scalable training assets.
• Identify gaps in client AI adoption and recommend targeted training interventions to client account teams.

Skills

Training delivery

Curriculum design

Public speaking

Technical enablement

AI workflow training

Education

Juris Doctor (JD)

Tools

LMS platforms

Video production tools

Job description

Syllo is seeking an AI Workflows Training Lead to own the content and delivery of all AI workflow training for internal teams and external clients. You will translate complex AI functionality into practical instruction for paralegals, attorneys, and legal ops professionals.

You will design the curriculum, deliver live and recorded sessions, and tailor enablement content to different user personas, while updating materials as the platform evolves.