Litigation AI Training Lead

Syllo; United States; Remote; USD 130,000 - 160,000; Full time

Job summary

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

You'll design curricula, run live sessions and create scalable assets, collaborating with product and engineering to align training with new features and client needs.

Qualifications

• 3+ years of litigation experience; JD preferred.
• Strong presentation skills for mixed audiences including directors to attorneys.
• Experience in training, curriculum design or technical enablement with AI tools.
• Experience training legal audiences is a strong plus.
• Ability to translate complex AI features into clear instructional content.
• Experience collaborating with product or engineering to track feature releases.
• Familiarity with LMS platforms and video production tools is a plus.

Responsibilities

• Design, build, and maintain the AI workflows curriculum for internal and external audiences.
• Deliver live training sessions and recorded modules on Syllo’s AI workflow features.
• Develop enablement content for different user personas based on fluency and role.
• Update training materials to reflect platform updates.
• Collaborate with the Instructional Designer on scalable training assets.
• Identify gaps in client AI adoption and propose targeted training interventions.

Skills

presentation skills

training experience

instructional content

product/engineering collaboration

audience adaptation

LMS familiarity

learning content design

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 workspace
that enables lawyers to safely harness the power of language models. After spending years
developing our cloud-based application, Syllo’s platform is now used by a wide range of legal
professionals — 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 and
engineers. We hold each other accountable to achieve ambitious goals in a timely way while
treating one another with respect and understanding. If you’re excited about AI and passionate
about 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, you
own the content and delivery of all AI workflow training for both internal teams and external
clients. 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 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.

Qualifications

Note: this is a wish list. Please do not hesitate to apply if you only have some of these
qualifications, especially if you come from a less traditional background. 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.

• 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

Capabilities

• Subject matter depth: you understand how Syllo’s AI features work and can explain
  them 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 evolvesCollaboration: you work effectively with product, engineering, and client account teams
  to 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