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AI Delivery Manager
nesto
Source: Headcount Labs · original listing ↗
Job data: Headcount Labs, ODbL 1.0. Job descriptions belong to their employers.
Posted Oct 26
About this role
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. Work Location and Language Requirements This 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 Hiring We 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. What You'll Be Doing • Implementation across the condition families. You support every agent in the workstream from start to finish: scoping, process mapping, golden-set (reference dataset) labeling queues, config logs, tuning, and shadow divergence queues (cases where agent output differs from underwriter decisions). • The client underwriter pod. You lead the client’s underwriter pod as an extended part of your team. First comes a calibration exercise: both pods label the same 50 documents, you measure disagreement, and you write the adjudication rules. Then production labeling begins, and you manage throughput. • Adjudication. You close every ambiguous label or policy question within SLA. You triage rigorously so only true policy calls reach the UW Expert. • Process mapping and value baselines. You co-own the signed process blueprints and the value baselines (touches, cycle time, rework). All results are measured against them. • The playbook. You document the patterns from the first workstream and build the repeatable playbook for future implementations. • Program artifacts and dependencies. 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 escalate risks early. What You Bring • Relevant Experience: 3–5 years as an Implementation Manager, Functional Consultant, Solutions-Oriented Analyst, or a similar role focused on technology implementation or operational transformation. • System Mastery: You learn complex software platforms quickly and turn that knowledge into practical solutions for the client’s operations. • Client-facing Experience: You run client workshops and manage client teams with confidence. • Technical comfort: You don’t need to code. You do speak the language of Technical Product Managers and can lead in-depth discussions on system logic. • Ownership: You’ve led client implementations as the primary person responsible for the functional outcome, and you’ve owned deliveries end to end. • Influence: You guide executive client decisions and push product improvements back to our team. Nice-to-Have • 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 Shouldn’t Apply If • You are not interested in a role that involves frequent client-facing work or extensive communication with numerous internal and external stakeholders. • You prefer working with legacy or simple systems. • You have no passion for the fintech or mortgage technology space and are unwilling to develop domain expertise. Interview Process • Recruiter Screen (30 min): A quick intro call to learn about your background and give you a real picture of the role. • Discovery Call (30 min): A conversation with the hiring manager to dig into your experience and assess mutual fit. • Case Study: A chance to showcase your skills through an open-ended, scenario-based exercise relevant to the role. • Case Study Interview (60 min): A deep dive into your submission, with time to get to know some team members and ask about the role and company. • 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. 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. 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. 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.