Engineering Manager, Conversational AI

Description

You will manage the Conversational AI engineering team at a company that lets businesses hire, pay, and manage employees in more than 185 countries, backed by over a decade of compliance expertise.

The team builds the company's conversational AI assistant, and this role suits a leader who wants to help define what AI-native software looks like.

Your team owns features from start to finish, including the APIs, data models, and services behind an LLM-based product and the chat interface users see.

You will stay hands-on while owning priorities, delivery, quality, and the growth of your engineers. The AI Architect sets the technical direction for conversational AI across the company, and your team turns that direction into shipped product.

Responsibilities

• Stay hands-on by building, reviewing, and shipping alongside your engineers, using AI tools directly in your daily work.
• Shape how the team works day to day, and keep refining those practices as the tools change.
• Help redesign how work is planned, built, reviewed, and shipped around AI, using Claude Code and other LLM harnesses to speed up experiments and product releases.
• Question inherited processes and keep only the ones that still earn their place.
• Work with product management, data teams, and the AI Architect to turn product goals and technical direction into a roadmap your team can deliver, aimed at your domain's acquisition and retention targets.
• Bring a clear technical view and test key decisions, while the AI Architect keeps ownership of architecture.
• Make sure your team's output runs on modern, scalable architecture built with React, TypeScript, and AWS.
• Recruit, mentor, and develop engineers with strong potential, combining human-led mentoring with AI-supported professional development.
• Keep observability and stability at a high standard.
• Make sure your domain's experiments and features meet strict quality benchmarks, even as delivery speeds up with AI tools.
• Work from the Toronto office Monday to Wednesday to build team cohesion and solve cross-functional problems faster.

Requirements

• At least 3 years of formal engineering management experience leading a team of engineers.
• You have changed how a team works because of AI tooling, not just added a tool. You can name the old practices you dropped and explain why.
• You have built backend microservices in TypeScript or Python, using Postgres and AWS, deployed on Kubernetes, with clean contracts and APIs that support agentic workflows.
• You have hands-on experience with LLM-based and agentic systems, including prompt design, tool and function calling, multi-step agent reasoning, and evaluation, and you know how to shape both how the assistant behaves and how that behavior reaches the user.
• You have a record of shipping customer-facing SaaS products, with a focus on metrics-driven growth, conversion, and user experience.
• You can turn complex technical and AI trade-offs into clear plans for leadership and cross-functional partners.

Conditions

The role is based at the Toronto office, Monday to Wednesday.

The company is an equal opportunity employer and makes hiring decisions based on qualifications, merit, and business needs, without discrimination on any protected basis.

Benefits

• Flexible time off.
• Parental leave.
• Health and dental insurance, where applicable, covering you and your family.
• Retirement savings plan and an employee incentive plan that shares company success.