Top Tech Jobs & Startup Jobs in Montreal

Owns and establishes Payments GTM Operations for Jobber’s fintech business. The role coordinates Marketing, Sales, Account Management, Support, Risk, Operations, Analytics, and Product to increase payments adoption and revenue. Responsibilities include mapping customer journeys, designing growth experiments and incentives, defining performance metrics, using data to identify opportunities and measure impact, improving customer-facing motions, and building scalable operating processes. The role also requires cross-functional stakeholder leadership and strategic partnership with senior executives.

Conduct fraud alert reviews, investigate suspicious merchant and transaction activity, apply risk controls, communicate with customers, support complex investigations, and improve fraud prevention processes. Analyze fraud patterns, recommend mitigation strategies, and collaborate cross-functionally to balance financial loss prevention with customer experience. Requires autonomous decision-making, strong communication, and availability during holidays as needed.

Build and own production AI systems as the founding technical engineer within Jobber’s Office of the CEO. Architect systems end to end, including LLMs, retrieval, agents, integrations, permissions, security, reliability, and quality. Embed with teams to deliver AI into real workflows, evaluate build-versus-buy decisions, run rapid proofs of concept, and establish trustworthy AI standards. The role requires executive communication, pragmatic technology choices, and Staff-plus experience delivering systems used daily at scale.

Build and own production AI systems as Jobber’s founding AI engineer. The role covers end-to-end architecture, retrieval quality, permissions, security, reliability, LLMs, agents, integrations, and workflow deployment. You will partner with teams and executives, evaluate build-versus-buy options, run rapid proofs of concept, establish technical standards, and deliver trustworthy AI systems used across the company.

Lead zero-to-one discovery, validation, launch, and scaling of Jobber’s new fintech products, including insurance, financing, card, banking, and spend-management offerings. Evaluate build-buy-partner strategies, manage embedded finance and banking-as-a-service partnerships, define MVPs and roadmaps, and make evidence-based investment decisions. Collaborate with Design, Engineering, Data, Risk, Compliance, Legal, Finance, and go-to-market teams while shaping product strategy and standards across the fintech organization.

The Director of Software Engineering role focuses on enhancing Jobber's AI capabilities, overseeing the integration of intelligent workflows across products to support small business operations more effectively.

Lead the design and delivery of an end-to-end AI system layer across the product: agentic workflows, orchestration, evaluation, guardrails, observability, and developer platform. Build and grow a multi-team org, partner with Product and Design, define how AI decisions flow across cross-product context, and ensure reliable, measurable, and safe autonomous behaviors that proactively help small-business users.