The bright side of mortgages nesto is Canada’s leading digital residential mortgage lender, offering Canadians the lowest rates from the get-go — with total transparency and no haggling.
About Us 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. Fast, simple, and fully digital, nesto has been recognized as CLA Lender of the Year for three consecutive years. That's the bright side of mortgages.
Nesto Group 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. Learn more at:
Life at nesto 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.
Work Location 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.
Why We Are Hiring 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 managing AI production systems trade‑offs (cost, latency, etc.)
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 We believe great people do their best work when they're supported professionally, personally, and financially. That's why we offer a comprehensive rewards package designed to help you thrive at every stage of your career.
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.
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Senior Applied AI Engineer in Winnipeg employer: Software Directory
At PolicyMe, we pride ourselves on being a remote-first startup that is revolutionizing the insurance industry with cutting-edge technology and a collaborative work culture. Our commitment to employee growth is evident through generous professional development budgets, regular performance reviews, and a supportive team environment that values autonomy and accountability. With competitive compensation, comprehensive benefits, and the opportunity to work from anywhere in Canada, joining us means being part of a high-performing team dedicated to making insurance simpler and more accessible for all Canadians.