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 a software company in the legal space that offers an AI-powered litigation workspacethat enables lawyers to safely harness the power of language models. After spending yearsdeveloping our cloud-based application, Syllo's platform is now used by a wide range of legalprofessionals — from the largest law firms in the world to the most prestigious law schools.We are a lean, fast-moving, and multi-disciplinary company led by exceptional lawyers andengineers. We hold each other accountable to achieve ambitious goals in a timely way whiletreating one another with respect and understanding. If you're excited about AI and passionateabout being part of a remote team that seeks to transform the legal practice, then read on!

We are seeking an AI Workflows Training Lead to join our training department. In this role, youown the content and delivery of all AI workflow training for both internal teams and externalclients. You will translate complex AI functionality into practical instruction for paralegals,attorneys, and legal ops professionals.

Key responsibilities

• Design, build, and maintain the AI workflows curriculum for both internal and externalaudiences
• Deliver live training sessions and recorded modules covering Syllo's AI workflow features
• Develop enablement content specifically suited for different user personas, accountingfor 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 toclient account teams.

Note: this is a wish list.

• 3+ years of experience in litigation (JD preferred)
• Strong presentation skills and comfort presenting to mixed-expertise audiences, fromlegal technology directors to practicing attorneys
• Experience with training, curriculum design, or technical enablement, with directexposure 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 clearinstructional content
• Experience collaborating with product or engineering teams to track and interpretfeature releases
• Familiarity with LMS platforms, video production tools, and learning asset formats a plus

We value both current skills and proven potential, and will give you an opportunity to present your best foot forward as part of our hiring process.

Capabilities

• Subject matter depth: you understand how Syllo's AI features work and can explainthem plainly to legal users
• Curriculum thinking: you design learning experiences that build skill, not just awareness
• Pace: you keep training content current as the product evolves
• Collaboration: you work effectively with product, engineering, and client account teamsto stay ahead of what clients need to know
• Communication: you adapt your register for the audience in front of you

Compensation will be negotiated based on your qualifications and experience, with a salary range of $130 - 160K, with potential for a higher range for exceptional candidates. Total compensation package includes equity and benefits.

United States - Remote Pay Range$130—$160 USD