Engineering Manager, AI Conversation Platform

Stripe is hiring an Engineering Manager, AI Conversation Platform in Toronto, Canada. Level rates it ; you can apply on Stripe.

Level's read on this job

On Level's scale, this role is Builds AI ●●●●: the job is building AI systems.
The posting mentions LLMs, RAG and Python among its tools and skills.
Level classes it as a lead role.
Stripe has 720 other open roles on Level.

AI in this role

Lead an engineering team building LLM-based conversation platforms, RAG systems, and production machine learning models at Stripe.

llmsragpython

ragfine-tuningmachine-learningteam-management

Engineering Manager, AI Conversation Platform

Who we are

About Stripe

Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career.

About the team

The newly formed Conversation Platform team aims to build a conversation platform for all merchants who use Stripe. We are doing so by (a) automating the easy tasks, and (b) assisting our users in the difficult tasks. Some examples include customizing the Stripe landing page to suggest bespoke integrations, allowing users to command the Stripe API in natural language, and resolving user issues automatically. We are developing RAG based systems on the latest LLMs as well as fine-tuning our own models. We’re an end-to-end team going from ideas to models to shipping in production.

What you’ll do

Responsibilities

Driving an ambitious vision for AI/ML that benefits our users
Setting the technical & process direction for the team based on business goals
Brainstorm and coordinate product integrations with partner teams
Proposing new ideas and building prototypes
Be an integral part of a larger ML community internally & externally
Hire & develop a world-class team to deliver high-quality ML systems.
Coach engineers to help them grow in their careers and maintain a high bar

Who you are

We are looking for ML Engineering Managers who are passionate about using ML to improve products and delight customers. You have experience leading teams that develop streaming feature pipelines, build ML models, and deploy them to production, even if it involves making substantial changes to backend code. You are comfortable with ambiguity, love to take initiative, and have a bias towards action.

Minimum requirements

Have at least 4 years of experience managing ML teams
Experience working as a Machine Learning Engineer, Applied Scientist or equivalent Individual Contributor.
Lead by example in high-growth, high-impact, ambiguous environments
Have experience building & shipping ML systems.
Hold yourself and others to a high bar when working with production systems.
Thrive in a collaborative cross-functional environment

Preferred qualifications

Experience in shipping LLM & RAG systems

How we rate this

Engineering Manager, AI Conversation Platform at Stripe rates 90 out of 100 for how much of the daily work is AI. That makes it Builds AI (AI Level 4 of 4). The level is about AI in the job, not seniority.

Classification

Builds AI. The job is building AI systems.

●●●● Builds AI80 to 100
●●●○ Works on AI60 to 79
●●○○ Uses AI40 to 59
●○○○ Little AI0 to 39

Levels come from how often the tools, models and workflows of the role are named in the posting itself. Read the description and count the AI tools, models and workflows it names.

Key facts

Engineering Manager, AI Conversation Platform is an open job at Stripe.
Level rates this role AI Level 4 of 4: Builds AI.
The role is based in Toronto, Canada.
The job was posted on June 9, 2026.
Seniority: lead.
Applications are handled by Stripe. Apply on Stripe

Prepare for this job

Built from this posting and from similar jobs on Level.

Skills and AI tools this role asks for

RAGFine-tuningMachine learningTeam ManagementLLMsPython

Questions you could be asked

How would you design a retrieval step so the model answers from real data instead of guessing?
Walk me through fine-tuning a model: what data did you use, and how did you check the result?
Tell me about a project where machine learning was part of your work. What did you do?
Tell me about a project where team management was part of your work. What did you do?
Walk me through how you've used LLMs in your day-to-day work.

Adapt your resume

List these exact terms on your resume: RAG, Fine-tuning, Machine learning, Team Management, and LLMs. An applicant tracking system matches the wording, not the idea.
Attach one line of real, concrete experience to at least one of them. A tool named with nothing behind it rarely survives a human read.
Lead with what you built, trained or shipped. This role is judged on the AI system itself, not the tools around it.

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