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

UsAs 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, straightforward, 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 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.

Work Location and Language RequirementsThis role is open to candidates in Quebec and Ontario. It's primarily remote, with the option to work from any of our offices across both provinces. French is a strong asset, as we have partners across Canada.

Why We Are

HiringWe enable our partners to improve and streamline their mortgage lending operations through the Nesto Mortgage Cloud.



As the most advanced cloud-based mortgage technology in Canada, our SaaS solution offers a world-class omnichannel experience that consistently boosts volume, increases productivity, and reduces technology costs. Maestro, our AI-powered underwriting platform, already runs inside nesto, with AI agents making real-time, policy-based decisions, and we are now bringing it to financial institution clients through Nesto Cloud.

To drive the execution of our upcoming projects, we are looking for an AI Delivery Manager for Maestro specifically, who will focus on functional mastery and SaaS delivery. Implementation across the condition families. Then production labeling begins, and you manage throughput.

You close every ambiguous label or policy question within SLA. You triage rigorously so only true policy calls reach the UW Expert. You document the patterns from the first workstream and build the repeatable playbook for future implementations.

You co-own the RAID and decision logs with the Project Manager. You run the bi-weekly platform-program dependency sync (live client data, environments, release schedules) and escalat risks early. 3–5 years as an Implementation Manager, Functional Consultant, Solutions-Oriented Analyst, or a similar role focused on technology implementation or operational transformation. You learn complex software platforms quickly and turn that knowledge into practical solutions for the client’s operations.

You run client workshops and manage client teams with confidence.

Technical comfort: You do speak the language of Technical Product Managers and can lead in-depth discussions on system logic. You’ve led client implementations as the primary person responsible for the functional outcome, and you’ve owned deliveries end to end.



Knowledge of the lending lifecycle or the mortgage industry.

Experience with AI or automation rollouts in operations (labeling, QA sampling, exception handling). Fluency in French and English. You have no passion for the fintech or mortgage technology space and are unwilling to develop domain expertise. A conversation with the hiring manager to dig into your experience and assess mutual fit.

Final

Non-Technical Interview (60 min): You'll meet with the recruiter and two additional stakeholders for a final conversation before a decision is made.

Offer Stage: Pending successful background and role-specific vetting checks, you'll receive a formal offer to join the team. That’s why we offer a comprehensive rewards package designed to help you thrive at every stage of your career. Competitive compensation, performance incentives (where applicable), and recognition for your contributions.

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. Generous vacation (4 weeks), floater days, and statutory holidays to help you recharge. RRSP matching to support your long-term financial wellbeing.

Enhanced maternity and parental leave top-up programs.

Education assistance, mentorship, training, and opportunities to build your career across Nesto Group. At nesto, we're passionate about challenging the status quo and building a better mortgage experience and saving money on their mortgages for Canadians. If you’re looking to solve meaningful problems alongside ambitious, supportive teammates, you’ll feel right at home here.

Diversity, Equity & InclusionAt Nesto Group, we believe diverse perspectives make us stronger. 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. #

📌 Ai Delivery Manager (Winnipeg)
🏢 Nesto Cloud
📍 Winnipeg