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, 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 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 LocationHybrid, based in our Toronto or Montreal office.

In-office expectations vary with business needs. If you are based in Montreal, expect to travel to Toronto a couple of times per month.

Why We Are

HiringMaestro, our AI-powered underwriting platform, already runs inside nesto, with AI agents making real-time, policy-based decisions. You will be the first leader of client AI delivery.

Your mission is to run the program that puts a fleet of AI agents live in Canadian banks’ production environments. As our Director of AI Delivery, you'll own it end to end: the delivery plan, the pod, the day-to-day client relationship, and the evidence that moves each agent through requirements, testing, model-risk approval, live-file shadow, joint change management,



and progressive production activation. You will also write the repeatable deployment playbook we reuse for every client that follows.

Lead Maestro delivery. Set a clear delivery approach amid uncertainty and build trust with client executives. Call each stage exit against its written proof point across our 9 stages: scoping, process mapping, golden sets, configuration, evaluation, model governance, shadow, change management, and progressive production decisioning.

Lead a senior delivery pod (delivery managers, underwriting expert, data scientists, program PM) day to day. Guide the AI Delivery Managers as they gather requirements for each agent. Work with the assigned PM and the relevant delivery and technical colleagues to keep implementations moving.

Run the weekly review of agent performance evidence and turn it into build and tuning priorities for Engineering. Data Scientists produce the evidence. You review it and do not produce it yourself. Lead the model-risk relationship.

Lead the relationship with the client’s model-risk team. Land validation packages for each condition family and secure the risk and governance sign-offs that authorize shadow and production. Adjudicate divergences, re-validate for drift, and report value foregone to client executives each month.

Own change management and readiness. Build the deployment playbook. Write the repeatable process that takes AI agents from client requirements through testing and client approval into production. Document each agent’s deployment as you go.

You have a client-facing delivery background, as an engagement manager, Delivery Director, or Implementation Director. You have run senior delivery teams on client sites and led working sessions with EVP-level executives. You have led client AI implementations hands‑on, from requirements through production.

You know ML/AI delivery well enough to chair an eval review, question precision and recall trade-offs, and translate model evidence into language a risk committee can act on.

Experience implementing AI for banks or other regulated organizations, including model-risk validation.



Mortgage or retail-credit domain knowledge, or experience with staged production rollouts of decisioning systems. Comfort building the playbook while running it in a scale‑up.

You have delivered AI solutions for enterprise clients on high-visibility projects and know how to earn their stakeholders’ trust. You do well under high expectations on a project that matters deeply to the client. You work well with a growing team of delivery, product, and technical colleagues.

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. Why You'll Love Working HereWe believe excellent 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 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.

Family

Support – 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 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. #

📌 Director Of Ai Delivery (Winnipeg)
🏢 Nesto Cloud
📍 Winnipeg