Principal Machine Learning Engineer

EvenUp Inc; Toronto; Hybrid; CAD 150,000 - 200,000; Full time

Job summary

A technology company in Toronto is seeking a Principal Machine Learning Engineer to lead innovations in Document AI. This pivotal role requires 12+ years of experience and a PhD in a related field. Candidates will define technical vision and mentor the ML team while working in a hybrid setting. Attractive benefits package includes health insurance, flexible PTO, and retirement options for Canadian employees.

Benefits

Medical, dental, and vision insurance

Flexible paid time off

401(k) and RRSP options

Paid parental leave

Qualifications

• 12+ years of experience in machine learning, with a proven record of shipping multiple systems at scale.
• Recognized expertise in large-scale ML and LLMs, with strong publication, patent, or open-source contributions.
• Hands-on mastery of modern ML toolchains and programming.

Responsibilities

• Define and drive the technical vision for Document AI.
• Invent and deliver the next generation of Document AI and Conversational AI.
• Lead research-to-production innovation in machine learning.

Skills

Large-scale machine learning

Generative models

Deep learning

Reinforcement learning

Programming (Python, PyTorch, TensorFlow)

Education

PhD in Machine Learning or related field

Tools

Python

PyTorch

TensorFlow

Job description

Overview

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. 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.

At EvenUp, we leverage the power of technology to bring fairness and accessibility to the legal system. Large language models (LLMs) and generative AI are the foundation of our technology strategy, especially in Document AI: the ability to deeply understand, reason across, and generate legal and medical documents at scale. This is one of the largest opportunities in applied AI, and one of the most impactful.

Role

We are seeking a Principal Machine Learning Engineer, the highest individual contributor level at EvenUp, who will help define not just our technology roadmap, but the future of Document AI itself. This role is for someone who thrives on both vision and execution: pioneering new approaches in a fast-evolving field, while also shipping systems that redefine what is possible in legal technology.

This is a hybrid role with the expectation of working at least 3 days a week from one of our office hubs in San Francisco or Toronto.

What you\'ll do

• Help define and drive the technical vision at EvenUp, identifying the most impactful opportunities in generative AI and ensuring the company remains at the forefront of the rapidly evolving Document AI landscape.
• Invent and deliver the next generation of Document AI and Conversational AI, enabling robust understanding, reasoning, and generation across diverse legal and medical documents, as well as natural, accurate, and context-aware interactions with users through conversational interfaces.
• Lead research-to-production innovation in:

• Information Extraction & Reasoning: scalable multi-document entity / relation extraction, knowledge graph construction, and long-context reasoning.
• Generative Workflows: producing reliable, high-quality legal and medical documents with deep structural and semantic fidelity.
• Conversational AI: building advanced dialogue systems that empower legal professionals to interact with our platform, retrieve insights, and generate documents through natural language conversations.
• Retrieval-Augmented Generation (RAG): multi-hop retrieval, reasoning chains, and verifiable generation at scale.
• Evaluation & Trust: systematic benchmarking, reliability, factuality, and risk assessment of LLMs in high-stakes legal and medical domains.
• Efficient Training & Adaptation: parameter-efficient fine-tuning, distillation, multi-modal integration, and domain-specific pretraining strategies.
• Shape EvenUp\'s ML strategy and technical roadmap, working hand-in-hand with product, engineering, and leadership to ensure our Document AI capabilities directly drive company growth and customer impact.
• Act as a company-wide thought leader in generative AI, providing strategic advice to executives and influencing not just what we build, but how we prioritize and compete.
• Mentor and elevate the entire ML organization, fostering a culture of deep technical rigor, creativity, and excellence.

What we look for

• 12+ years of experience in machine learning, with a proven record of shipping multiple systems at scale and advancing the state of the art.
• PhD in Machine Learning, Computer Science, or related quantitative field, or equivalent experience demonstrating mastery.
• Recognized expertise in large-scale ML and LLMs, with strong publication, patent, or open-source contributions a plus.
• Ability to define and drive a technical vision that aligns with company strategy, even under uncertainty.
• Strong track record of innovation in deep learning, generative models, reinforcement learning, or probabilistic methods, with direct impact on real-world systems.
• Hands-on mastery of modern ML toolchains and programming (Python, PyTorch, TensorFlow, distributed training, large-scale data systems).
• Exceptional ability to translate cutting-edge research into robust, practical solutions that move the needle for customers.
• Demonstrated thought leadership and influence across organizations, with the ability to set standards and inspire others.

Why this role matters

This is a rare opportunity to operate at the frontier of generative AI in one of its most consequential applications. As Principal MLE at EvenUp, you won't just be solving technical challenges—you will be defining the roadmap of a company and shaping the trajectory of an industry.

If you want to push beyond today\'s limits of LLMs, invent the future of Document AI, and see your work translate into justice and fairness for millions of people, we\'d love to meet you.

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, [e-mail] or [e-mail] 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 [e-mail]. 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.