Engineering Manager, AI DocGen

TL;DR

Engineering Manager, AI DocGen: Leading and scaling a team building AI-native document generation workflows with an accent on driving execution across complex, mission-critical initiatives and guiding technical decision-making across architecture, system design, and AI integration. Focus on balancing innovation and pragmatism when scaling AI-driven products in production environments and fostering a culture of ownership, accountability, and continuous learning.

Location: Hybrid role in Toronto, Canada, with an expectation of being in the office three days per week. Work authorization for Canada is required.

Salary: CA$179,000–CA$314,000 or US$232,000–US$375,000

Company

hirify.global is a fast-growing vertical SaaS company using AI to empower personal injury lawyers and victims to achieve justice.

What you will do

• Lead and scale a team building AI-native document generation workflows.
• Drive execution of mission-critical initiatives, partnering with Product, Design, Legal, and Operations.
• Guide technical decision-making across architecture, system design, and AI integration.
• Champion engineering quality, reliability, and operational excellence, ensuring secure and compliant systems.
• Develop advanced AI workflows, including LLM-based systems, balancing innovation and pragmatism.
• Recruit, mentor, and develop engineers, fostering a culture of ownership and continuous learning.

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 cross-functional partners.
• Must be based in Toronto, Canada, for a hybrid work model (3 days/week in-office).

Nice to have

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

Culture & Benefits

• Choice of medical, dental, and vision insurance plans.
• Flexible paid time off, sick leave, and paid parental leave.
• 401(k) for US-based employees and RRSP for Canada-based employees.
• Home office stipend.
• Local in-person meet-up program and hubs in San Francisco and Toronto.