Senior Applied AI Engineer in Winnipeg

nesto is Canada’s leading digital residential mortgage lender, offering Canadians the lowest rates from the get-go — with total transparency and no haggling.

As Canada’s pioneer in online mortgage lending, nesto is transforming the way Canadians finance their homes. Our mission is to offer a positive, empowering, and transparent property financing experience, simplified from start to finish. Borrowers benefit from rates that are often lower than those offered by the big banks, along with an exceptional end-to-end mortgage experience powered by best-in-class AI technology.

Nesto Group is Canada’s leading provider of mortgage technology and financing solutions, with more than CAD $80 billion in residential and commercial mortgages under administration. Trusted by many of the country's leading financial institutions, we combine over 50 years of mortgage expertise with proprietary cloud and AI technology to transform the future of lending.

Powered by our proprietary cloud and AI technology, nesto has become one of Canada's fastest-growing mortgage lenders, gaining market share across direct-to-consumer (D2C) residential lending, the broker channel, and multi-family commercial lending. Recognized as one of Deloitte's Fast 50 companies for three consecutive years, we continue to push the industry forward through innovation, technology, and customer-focused solutions.

Operating through our family of brands—CMLS, nesto, and Nesto Cloud—our mission is to build Canada's mortgage ecosystem of the future and create a true Canadian champion in lending technology and financial services.

At nesto, we're passionate about challenging the status quo and building a better mortgage experience and saving money on their mortgages for Canadians. We foster a culture of collaboration, transparency, and creativity where every team member is empowered to take ownership, make an impact, and grow. If you're looking to solve meaningful problems alongside ambitious, supportive teammates, you'll feel right at home here.

This is a remote-first role open to candidates anywhere in Canada. You'll have the flexibility to work from home or from any of our offices nationwide.

nesto's AI Stream is building Maestro, our AI underwriting and lending engine. Maestro reads documents, applies credit policies automatically, and generates clear, auditable decisions in minutes. The team is in an active build phase with significant near-term delivery commitments, and we need a senior engineer who can take ownership of major projects and help set technical direction quickly.

What You'll Be Doing

• Lead major features and projects end-to-end, surfacing trade-offs clearly so delivery stays on track without compromising quality.
• Design and optimize agentic AI workflows that combine deterministic rules with LLM perception, embedding search, and structured output extraction.
• Build and own evaluation pipelines, including golden sets, offline and online evals, and regression tracking, to measure model quality over time.
• Shape architecture decisions for the AI agent platform, setting high technical standards through code reviews and collaborative problem-solving.
• Use AI tooling and agent harnesses to write and ship code faster, so the team can keep pace with its deadlines.
• Mentor peers and collaborate with cross-functional teammates to hit delivery timelines.

What You Bring

• 5+ years of professional software development experience, with strong backend and API skills.
• Strong Python skills and hands-on experience with LLMs, ideally running them in production (prompting, RAG, or structured extraction).
• A data science, data analysis, or statistics background.
• Experience with model implementation, monitoring, and evaluation across the full lifecycle.
• Solid software engineering fundamentals, including testing, design patterns, and agile practices.
• Comfort with AI-assisted development tooling and agent-based workflows.
• Experience leading projects or stepping into a technical lead role.

Nice-to-Have

• Familiarity with LLM orchestration frameworks (LangChain, LlamaIndex), vector databases, and document intelligence pipelines.
• Experience working in regulated domains, such as OSFI E-23 compliance.

This Role Might Be for You If

• You want to build something from the ground up and see it through, rather than move into people management.
• You've shipped LLM features to production and care about how they're evaluated.
• You're comfortable letting AI tooling accelerate how you write and review software.
• You've led projects before and are ready to take a tech lead role on product-oriented projects with real deadlines.
• You come from backend or API work and have built data skills alongside it.

Why You'll Love Working Here

• Competitive Rewards— Competitive compensation, performance incentives (where applicable), and recognition for your contributions.
• Health & Wellness— Comprehensive medical, dental, and vision coverage, Health & Wellness Spending Accounts (where applicable), telemedicine, Employee Assistance Programs, and mental health support for you and your family.
• Time to Recharge— Generous vacation (4 weeks), floater days, and statutory holidays to help you recharge.
• Planning for the Future— RRSP matching to support your long-term financial wellbeing.
• Family Support— Enhanced maternity and parental leave top-up programs.
• Learning & Growth— Education assistance, mentorship, training, and opportunities to build your career across Nesto Group.
• Tools for Success— Modern technology, collaborative teams, and the resources you need to do your best work.

Diversity, Equity & Inclusion

At Nesto Group, we believe diverse perspectives make us stronger. We are committed to fostering an inclusive workplace where everyone feels respected, supported, and empowered to succeed. We welcome applications from people of all backgrounds, including Indigenous Peoples (First Nations, Inuit, and Métis), persons with disabilities, members of racialized communities, women, and members of the 2SLGBTQIA+ community. If you require accommodation during any stage of the recruitment process, we are committed to working with you to meet your needs.