Senior AI Engineer in Toronto

Paddle offers digital product companies a completely different approach to their payment infrastructure. Instead of assembling and maintaining a complex stack of payments-related apps and services, we’re a Merchant of Record for our customers. That means we take away 100% of the pain of payment fragmentation. It’s faster, safer, cheaper, and, above all, way better.

We’re looking for an entrepreneurial and technically strong Senior AI Engineer to join our Data & AI team and work with our Go-To-Market organisation. This is a builder's role, end to end. You’ll work closely with Marketing, Sales, and RevOps to solve high-value problems, design practical AI solutions and build them into reliable systems that people use every day. You’ll be expected to move comfortably from an ambiguous business challenge to a technical design, a working prototype, and then a production-ready solution.

Your work could include building systems that segment and prioritise accounts, developing agents that automate sales workflows, or creating intelligent tools that help our teams research prospects and act on buying signals. You’ll own the full lifecycle of what you build, including evaluation, observability, reliability and cost optimisation.

This role is ideal for someone who enjoys being close to users, can write production-quality code and is excited by the challenge of turning rapidly evolving AI capabilities into valuable commercial outcomes. Experience working with GTM teams is useful, but the ability to understand problems, build effective systems and measure their impact is more important.

What you'll do:

• Design and build AI-powered systems for account segmentation, enrichment, scoring, prioritisation and buying-signal detection
• Develop and deploy agentic workflows for use cases such as account research, outbound personalisation, call summarisation and CRM hygiene
• Write production-quality code and build the integrations, data pipelines and services required to take solutions from prototype to reliable daily use
• Optimise systems for quality, latency and cost through evaluation, prompt design, model selection, routing, caching, context management and token optimisation
• Establish practical patterns for building AI systems at Paddle, including monitoring, guardrails, documentation and clear measures of business impact

We'd love to hear from you if you:

• Have strong software engineering experience and can independently take a problem from technical design through to production; Python and SQL experience would be particularly relevant
• Have hands-on experience building applications with large language models, APIs, retrieval systems, agents or other applied AI technologies
• Understand how to evaluate and operate AI systems in production, including managing hallucination risk, latency, reliability, context limits and variable model costs
• Are comfortable working with structured and unstructured data, building integrations and turning information from multiple sources into useful systems
• Have an interest in commercial problems and can understand concepts such as ICP, segmentation, pipeline, buyer intent and sales workflows; direct GTM experience is beneficial but not essential
• Enjoy working directly with the people who use what you build, are comfortable with ambiguity and can balance speed, quality, and long-term maintainability

At Paddle, we’re committed to removing invisible barriers, both for our customers and within our own teams. We recognise and celebrate that every Paddler is unique and we welcome every individual perspective. As an inclusive employer we don’t care if, or where, you studied, what you look like or where you’re from. We’re more interested in your craft, curiosity, passion for learning and what you’ll add to our culture. We encourage you to apply even if you don’t match every part of the job ad, especially if you’re part of an underrepresented group. Please let us know if there’s anything we can do to better support you through the application process and in the workplace. We will do everything we can to support any accommodations needed. We’re committed to building a diverse team where everyone feels safe to be their authentic self. Let’s grow together.

Our Values

• Paddle Together- “None of us, is as smart as all of us”
• Paddle Simply- “Simple can be harder than complex: you have to get your thinking clean to make it simple”
• Paddle for others- “We can realise our wildest dreams, so long as we help enough other people to realise theirs”

Why you’ll love working at Paddle

We are a diverse, growing group of Paddlers across the globe who pride ourselves on our transparent, collaborative and respectful culture. We are a ‘digital-first’ company, which means you can work remotely, from one of our stylish hubs, or even a bit of both! We offer all team members unlimited holidays and 4 months paid family leave regardless of gender. We invest in learning and will help you with your personal development via constant exposure to new challenges, an annual learning fund, and regular internal and external training.