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.