Staff Machine Learning Engineer - LLMs & Document AI

EvenUp is on a mission to close the justice gap using technology and AI. We empower personal injury lawyers and victims to get the justice they deserve. Our products enable law firms to secure faster settlements, higher payouts, and better outcomes for victims injured through no fault of their own in vehicle collisions, accidents, natural disasters, and more.

We are one of the fastest-growing vertical SaaS companies in history, and we are just getting started. EvenUp is backed by top VCs, including Bessemer Venture Partners, Bain Capital Ventures, SignalFire, and Lightspeed. We are looking to expand our team with talented, driven, and collaborative individuals who seek to have a lasting impact. Learn more at www.evenuplaw.com.

Join EvenUp as a Staff Machine Learning Engineer and build the future of personal injury law technology. This is a unique opportunity to lead the development of high-visibility, high-impact generative AI models that are core to our customer experience and business growth. You will tackle the most complex legal document challenges, turning raw legal and medical data into production-ready models that power Piai™, our proprietary claims-intelligence platform.

You’ll partner closely with Product, Research, and Engineering leaders to shape our modeling strategy, owning critical areas like Document AI, LLM fine-tuning, and sophisticated information retrieval. In this high-priority role, you’ll be empowered to drive innovation, mentor a top-tier ML team, and set the vision for how machine learning will shape both our customer impact and company success. The right leader will see their work translate to tangible product launches, a robust ML foundation, and a direct influence on the success of an ambitious, fast-growing company.

What you’ll do:

• Design and refine advanced Document AI models for entity/relationship extraction, document structure understanding, and sophisticated reasoning from complex legal and medical text.
• Solve complex modeling challenges involving long-context and multi-document reasoning, including context segmentation and the aggregation of distributed facts.
• Lead LLM fine-tuning initiatives, applying techniques like reinforcement learning with verifiable reward signals and parameter-efficient fine-tuning (e.g., LoRA, QLoRA).
• Establish rigorous evaluation standards to reduce hallucinations, improve factual consistency, and handle ambiguous or noisy data.
• Drive data excellence by conducting hands-on analysis to ensure high-quality training and evaluation datasets, managing edge cases, noise, and data drift.
• Experiment with and benchmark advanced prompt engineering techniques (few-shot, chain-of-thought), balancing context length with extraction accuracy.
• Provide technical leadership and mentorship to a team of ML engineers and data scientists, fostering a culture of technical excellence and continuous growth.
• Collaborate cross-functionally with product, engineering, and legal subject-matter experts to translate ambiguous research goals into impactful production solutions.
• Act as a bridge between cutting-edge research and practical application, ensuring new techniques are integrated into our production frameworks effectively.
  
  

What we look for:

• A true builder’s mentality: ready to launch, scale, and shape a new technical domain within a rapidly growing company.
• Deep domain expertise in machine learning, NLP, and LLMs, with a track record of solving complex modeling challenges and deploying models in operational settings.
• Expertise in advanced ML techniques, including deep learning, reinforcement learning, probabilistic modeling, or optimization.
• Strong record of mentorship, with a passion for guiding team members and establishing best practices for experimentation and benchmarking.
• Experience and comfort with modern ML engineering languages and frameworks—specifically high proficiency in Python and major LLM technologies.
• Excellent communication skills, with the ability to partner closely with both technical and non-technical stakeholders to deliver business-impactful solutions.
  
  

Minimum qualifications:

• 5 years of hands-on professional experience in machine learning engineering or related fields, with multiple models deployed in operational settings.
• Strong proficiency with the latest LLM technologies and a demonstrated ability to apply cutting-edge research to practical solutions.
• High proficiency in Python and a deep understanding of modern ML/NLP frameworks.
• Demonstrated ability to lead technical strategy, mentor team members, and drive execution in fast-paced, ambiguous environments.
• Experience working in a high-growth startup environment.
• Excellent cross-functional leadership skills, with a track record of partnering closely with Product and Engineering stakeholders.
  
  

Preferred qualifications:

• PhD in Machine Learning, Computer Science, or other quantitative fields.
• Passion for EvenUp's mission of driving fairness and accessibility in the legal domain.
• Ability to work in a hybrid setting from one of our office hubs in Toronto or San Francisco.
  
  

Notice to Candidates:

EvenUp has been made aware of fraudulent job postings and unaffiliated third parties posing as our recruiting team – please know that we have no affiliation or connection to these situations. We only post open roles on our career page (evenuplaw.com/careers) or reputable job boards like our official LinkedIn or Indeed pages, and all official EvenUp recruitment emails will come from the domains @evenuplaw.com, @evenup.ai, @ext-evenuplaw.com, no-reply@ashbyhq.com or no‑reply@canditech.io email addresses.

To ensure fairness and proper consideration, we do not accept resumes or expressions of interest via email or social media messages. If you’re interested in a role, please submit your application directly through our careers page.

If you receive communication from someone you believe is impersonating EvenUp, please report it to us at talent-ops-team@evenuplaw.com. Examples of fraudulent domains include “careers-evenuplaw.com” and “careers-evenuplaws.com”.

Benefits & Perks:

As part of our total rewards package, we offer attractive benefits and perks to our employees, including:

• Choice of medical, dental, and vision insurance plans for you and your family.
• Additional insurance coverage options for life, accident, or critical illness.
• Flexible paid time off, sick leave, short-term and long-term disability.
• 10 US observed holidays, and Canadian statutory holidays by province.
• A home office stipend.
• 401(k) for US-based employees and RRSP for Canada-based employees.
• Paid parental leave.
• A local in-person meet-up program.
• Hubs in San Francisco and Toronto.
  
  

Please note the above benefits & perks are for full-time employees

EvenUp is an equal opportunity employer. We are committed to diversity and inclusion in our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Compensation Range: $222K - $300K