Engineering Manager, Conversational AI

Purpose in Every Position Pebl puts a world of talent at your fingertips. With our AI-powered Global Work Platform™, companies can hire, pay, and manage employees in 185+ countries—removing risk, red tape, and guesswork from global growth. Backed by more than a decade of compliance leadership and local expertise, Pebl helps businesses move fast, stay compliant, and scale with confidence. With Pebl, companies everywhere can hire great talent anywhere. Where Your Work Moves the Needle. At Pebl, every team member drives our success. Joining us means more than filling a role—you’re accountable for results and impact. Our values guide how we operate, execute, and collaborate across borders. By putting them into action, you’ll help us scale faster, compete harder, and lead the future of global work. Position Summary We are looking for a hands-on Engineering Manager to lead our high-impact Conversational AI team. This is a critical leadership role for someone who is not only an effective manager but also an active practitioner in the AI-augmented development era. We're not just building a chatbot, we're rethinking what it means for software to work with you, not just for you. Our Conversational AI team is building Alfie, our conversational AI assistant, and we're looking for an engineering leader who wants to help define what AI-native software looks like. You'll lead a team of engineers who own features end to end: the APIs, data models, and services behind our LLM-based product, and the conversational interface people actually use. You're equally comfortable designing a tool-calling contract and shaping what a user sees when the model gets something wrong. You have hands-on experience building LLM-based and agentic products, and you've shipped something real end users, not just developers, interact with. You'll partner closely with our AI Architect, who sets technical direction for conversational AI across Pebl. You own how the team turns that direction into shipped product: priorities, delivery, quality, and growing the people doing the work. Responsibilities - Hands-On Team Leadership: Lead by example. Build, review, and ship alongside your team, working directly with AI tools rather than managing around them. Champion how your team works day to day, and keep improving it as the tools change. - AI-Native Execution: We're redesigning how we build software around AI, not bolting AI onto existing processes. You'll help us rethink how work gets planned, built, reviewed, and shipped, using Claude Code and other LLM harnesses as core parts of the workflow to accelerate experimentation and product velocity. We want someone who questions inherited ceremonies, not someone who reinstalls them. - Roadmap & Technical Partnership: Work with product management, data teams, and our AI Architect to turn product goals and technical direction into a roadmap the team can execute, in service of your domain's acquisition and retention goals. You'll bring a strong technical point of view and pressure-test decisions, while architectural direction stays with the AI Architect. Ensure your team's output is built on modern, scalable architecture using React, TypeScript, and AWS. - Team Growth & Mentorship: Recruit, mentor, and grow high-potential engineers. Balance "human-led" mentorship with "AI-augmented" professional development. - Operational Excellence: Maintain high observability and stability standards. You are responsible for ensuring your domain's experiments and product features meet rigorous quality benchmarks, even as we accelerate delivery with AI tools. - On-Site Collaboration: Foster a collaborative in-person environment in our Toronto office (Mon–Wed) to build team cohesion and drive faster cross-functional problem solving. Qualifications & Skills - Management Experience: 3+ years of formal experience in engineering management leading a team of engineers. - AI-First Mindset: You've changed how a team works because of AI tooling, not just adopted a tool. You can describe which old practices you dropped and why. - Technical Stack: Demonstrated ability to operate backend (micro)services in TypeScript or Python, Postgres, and AWS, deployed on Kubernetes, including clean contracts and APIs that support agentic workflows. - AI Expertise: Hands-on experience with LLM-based and agentic systems — prompt design, tool/function calling, multi-step agent reasoning, evaluation — to shape both how the assistant behaves and how that behavior surfaces to the user. - Growth Mindset: Proven track record of delivering customer-facing SaaS products with a focus on metrics-driven growth, conversion, and user experience. - Communication: Ability to distill complex technical/AI-related trade-offs into actionable plans for leadership and cross-functional partners. Our Commitment to You At Pebl, we’re committed to supporting our team with comprehensive rewards and benefits designed to meet diverse needs across roles and locations. Our core offerings include: - Flexible Time Off – Take the time you need to recharge. - Parental Leave – Support for growing families. - Health and Dental Insurance – Where applicable, to cover you and your loved ones. - Retirement Savings + Employee Incentive Plan – Plan for the future while sharing our success. Please visit our career page for more information https://hellopebl.com/company/careers/. Pebl is an Equal Opportunity Employer. We power global teams and believe diverse perspectives drive innovation and impact. Employment decisions at Pebl are based on qualifications, merit, and business needs. We do not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, or gender identity), national origin, age, disability, genetic information, veteran status, or any other status protected by applicable law. We’re committed to fostering an inclusive culture where every teammate can thrive and do the best work of their career—anywhere in the world.