The salary range provided reflects the compensation that EvenUp reasonably expects to offer for this role. The specific salary within this range will be determined based on various factors, including the candidate's relevant experience, education, skills, location, and alignment with the role's responsibilities.

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.

🎥 Life as an Engineer at EvenUp

Location & Work Model

This is a hybrid role, with an expectation of being in our Toronto office three days per week.

About the Team

EvenUp’s document products empower attorneys to represent their clients more effectively and secure better outcomes. With over $1.5B in damages claimed to date, the Document Generation team is developing an industry-leading, AI-native platform for generating legal documents in personal injury law.

As Engineering Manager for Document Generation, you will lead a high-impact team building the systems at the core of EvenUp’s business. You’ll balance strategic leadership with hands-on technical contribution, collaborating closely with founders, product, and cross-functional partners to scale AI-native workflows that directly advance EvenUp’s mission to ensure personal injury victims receive fair compensation.

Responsibilities

• Lead and scale a team building AI-native document generation workflows

• Drive execution across complex, mission-critical initiatives tied to EvenUp’s core products

• Partner with Product, Design, Legal, and Operations to deliver high-quality, customer-centric solutions

• Establish and uphold a high bar for engineering quality, reliability, and operational excellence

• Guide technical decision-making across architecture, system design, and AI integration

• Use data-driven insights to continuously improve delivery velocity, quality,

What You’ll Do

• Team Leadership & Strategy: Set and communicate a clear technical and execution vision aligned with EvenUp’s broader goals. Lead engineers through the full software lifecycle, from planning and architecture to deployment and monitoring. Foster a culture of ownership, accountability, collaboration, and continuous learning

• Product & AI-Native Development: Guide the development of advanced AI workflows, including LLM-based systems and expert-review pipelines. Balance innovation and pragmatism when scaling AI-driven products in production environments. Contribute hands-on as needed, particularly in complex or high-impact technical areas

• Cross-functional Collaboration: Work closely with founders, product managers, designers, and stakeholders to scope, prioritize, and deliver initiatives. Translate business and customer needs into clear technical direction for the team

• Engineering Excellence & Operations: Champion best practices across architecture, coding standards, testing, security, observability, and reliability. Ensure systems handling sensitive data are secure, compliant, and production-ready. Oversee operational ownership, including incident response, on-call health, and reducing operational toil

• Mentorship & Growth: Recruit, mentor, and develop engineers through regular feedback, coaching, and career development. Support performance management, growth planning, and team health

What We Look For

• 4+ years of direct people-management experience leading software engineering teams

• Proven ability to ship and scale complex, high-quality software systems

• Strong technical background with experience in distributed systems and modern backend architectures

• Demonstrated success balancing strategic leadership with hands-on technical contribution

• Experience leading teams in fast-paced, high-growth environments

• Excellent communication skills and ability to influence across cross-functional partners

• Strong sense of ownership, accountability, and bias toward execution

Bonus

• Experience or strong interest in AI/ML, LLM-based systems, or legal tech

• Background in AI-native or social impact–driven products

#LI-Hybrid

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: CA$179K - CA$314K