Associate Legal Technology Jobs in Chicago, IL (NOW HIRING)

Job Description

Ready to Help Shape the Future of Legal Tech?!

At Litera, we don't just build software, we transform how the world's top law firms operate. Every day, we RaiseTheBar for what's possible through AI, innovation, and solutions that power millions of legal professionals worldwide. If you're energized by scale, real impact, and meaningful challenges, you'll feel right at home here.

Where You'll Work

Hybrid: This is a hybrid role based in Toronto, Austin, Chicago, Denver, New Jersey, Philadelphia, or Raleigh with the expectations to be in office at least 3 days a week for collaboration and connection.

Why this Role Matters

As our Associate, Legal Engineering, you'll play a key role in shaping how Litera's AI-powered products understand and analyze complex legal documents. You'll partner closely with product, engineering, and design teams to drive the development of intelligent features grounded in real legal workflows, and your work will directly influence the accuracy, usability, and value our tools deliver to the world's leading law firms, professional service firms, and corporations. This is a high-visibility role ideal for someone who thrives in a fast-moving, collaborative environment and wants to make a measurable difference from day one.

What You'll Deliver

• Product vision for legal AI. Partner with product, engineering, and design teams to define the roadmap for Kira and other Litera legal tech products, ensuring every feature reflects how lawyers actually work.

• High-performing machine learning models. Develop and refine "smart fields" - ML algorithms that automatically locate key provisions in securities, financing, and other transactional documents - so clients spend less time on manual review.

• Optimized generative AI experiences. Experiment with and validate LLM-driven prompting within Litera products, raising accuracy and usability for end users.

• Domain expertise that keeps Litera ahead. Maintain deep awareness of developments in transactional law and continuously identify new document types and data points worth building into the platform.

• Legally sound product workflows. Advise engineering teams on how legal processes work in practice, preventing design choices that would create friction for attorneys.

• Scalable quality standards. Train and validate models across diverse document sets, ensuring consistent, reliable output that clients can trust at scale.

• Process improvements and best practices. Identify inefficiencies in current workflows and recommend changes that accelerate delivery and improve product quality.

• Client-ready solutions. Translate complex legal concepts into actionable product requirements that deliver measurable value to the world's leading firms and corporations.

We're committed to creating an inclusive environment. If you need accommodations at any point in the process or in the role, we're here to support you.

What You'll Bring

Must-Haves:

• JD with active bar admission in at least one U.S. state or Canadian province.

• Two or more years of transactional law experience at a law firm, in-house legal team, or legal service provider.

• Strong interest in legal technology and artificial intelligence, with a willingness to experiment with new tools.

• Exceptional attention to detail, analytical skills, and ability to manage multiple priorities simultaneously.

• Excellent written and verbal communication skills paired with a client-service mindset.

• Self-motivated and able to work independently while collaborating effectively across cross-functional teams.

Nice to Haves:

• Experience in debt financing transactions.

• Background in legal operations, legal program management, or contract management systems.

• Hands-on exposure to AI, machine learning, or generative AI tools.

• Prior experience working with or within a legal technology company.

We know great candidates don't always check every box. If you're excited about this role, we encourage you to apply.

What You'll Experience

• A team that shows up. Work alongside people who collaborate, support one another, and lead with integrity.

• Global Reach. Partner with teams around the world to solve complex challenges that matter.

• Real opportunity for growth. Expand your impact through meaningful stretch opportunities, visibility and career development.

• AI-driven innovation. Work at the intersection of legal technology, customer outcomes, and cutting-edge AI.

Pay Transparency for Colorado, Illinois, and New Jersey:

The base salary range for this role is $80,000 to $97,000 USD. Final compensation will be determined based on experience, skills, education, and other relevant qualifications. This role is also eligible to earn commission based on performance.

Pay Transparency for Ontario Applicants

The base salary range for this role is $115,000 to $133,000 CAD. Final compensation will be determined based on experience, skills, education, and other relevant qualifications. This role is also eligible to earn commission based on performance. In addition to base salary, Litera offers a comprehensive benefits package, including medical, dental, and vision coverage, retirement savings plan with company match, and incentive and recognition programs. Benefits are subject to eligibility requirements.