Director of Machine Learning

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.

We are seeking a Director of Machine Learning to help build and lead a critical new ML function at EvenUp. Reporting directly to the Head of Data Science, you will establish ownership and direction across several high-impact, GenAI-heavy product areas, including Document Generation, Agentic Systems (including Voice Agents), Data and Knowledge Management, and more.

You will join at a formative stage, with the opportunity to define strategy, set technical direction, and build a team from the ground up. This leadership role is highly visible and influential in shaping EvenUp’s AI-first product roadmap.

You will collaborate closely with Product and Engineering leaders to move beyond ad-hoc solutions and establish principled, scalable machine learning systems that power customer-facing experiences. This role is ideal for a builder who thrives in ambiguity, enjoys scaling teams and systems, and is excited to work at the cutting edge of applied LLMs and generative AI.

Hybrid: This role will be based from our Toronto office 3x per week

• Build, lead, and grow a high-performing Machine Learning team, starting from a small initial footprint

• Own and drive ML strategy and execution across Document Generation, Voice Agents, and Knowledge Base systems

• Partner closely with Product and Engineering to define roadmaps, priorities, and technical approaches

• Establish best practices for applied ML, LLM usage, and generative AI systems in production

• Deliver meaningful product impact quickly while laying a strong foundation for long-term scale

• Proven experience leading and managing ML or data science teams, ideally in fast-paced or startup environments

• Deep technical expertise in machine learning, NLP, generative AI, and LLMs

• Knowledge and experience in fine-tuning and post-training LLMs, reinforcement learning, etc.

• Ability to operate at both a strategic and hands-on technical level when needed

• Strong cross-functional communication skills and experience working closely with Product and Engineering

• A builder mindset with experience standing up new teams, systems, or technical domains

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, [email protected] or no‑[email protected] 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 [email protected]. 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.