Hybrid Senior Engineering Manager, AI DocGen

at EvenUp

• Job title: Senior Engineering Manager, AI DocGen
• Job type: Full Time
• Experience level: Senior
• Salary: CA$179,000 - CA$314,000 per year
• Degree requirement: Bachelor's Degree
• Tech skills: Distributed Systems
• Location requirements: Hybrid, Toronto, Canada

About the role

• Engineering Manager leading AI-native document generation workflows for EvenUp in the legal tech sector. Collaborating with cross-functional teams to drive mission-critical initiatives.

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
• 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
• 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
• Work closely with founders, product managers, designers, and stakeholders to scope, prioritize, and deliver initiatives
• 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
• Recruit, mentor, and develop engineers through regular feedback, coaching, and career development
• Support performance management, growth planning, and team health

Requirements

• 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
• Experience or strong interest in AI/ML, LLM-based systems, or legal tech
• Background in AI-native or social impact–driven products

Benefits

• 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