Director, Software Engineering (AI Workflows & Ecosystem)Jobber222k-300k CADFull-timeremote
· leadCanadallmListed via Jobicy
· posted 17 Oct 2026. Apply on Jobicy## DescriptionAre you driven to bring people, technology, and strategy together to build impactful software?Jobber exists to help people in small businesses be successful. We work with small home service businesses, like your local plumbers, painters, and landscapers, to transform the way service is delivered through technology. With Jobber, they can quote, schedule, invoice, and collect payments from their customers while providing an easy and professional customer experience. Running a small business today isn’t like it used to be—the way we consume and deliver service is changing rapidly, technology is evolving, and customers expect more. THE PROBLEM YOU’D OWNJobber has AI in production, but not yet at its full potential.
We already have AI answering calls, drafting responses, and powering parts of our product. A service pro still has to:-Manually follow up on jobs-Piece together context across workflows-Decide what to do nextThe platform doesn’t proactively help them run their business. AI-powered features → AI-powered workflows → AI-powered business operationsThis role owns that shift. THE CUSTOMERYou’re building for people who don’t have time to think about software.-A plumber finishing their last job at 6 pm-A cleaner managing 30 clients and 5 employees-A landscaper juggling scheduling, payments, and follow-upsThey’re not asking for “AI.” This isn’t about building clever systems; it’s about building systems that remove thinking from already overwhelmed people.
WHAT YOU’D OWNEnd-to-end ownership of Jobber’s AI system layer. You’re owning how intelligence flows across the entire product.
Product + Platform Scope-AI Foundations (models,



orchestration, evals, guardrails)-Copilot (user-facing intelligence layer)-Automations (workflow execution layer)-Platform Experience / Marketplace (integration + ecosystem surface)-Emerging surfaces (voice, messaging, cross-product intelligence)What this actually meansYou are responsible for:-How decisions get made inside the system-How context moves across workflows-How actions get triggered (and when they shouldn’t)-How we evaluate whether AI is actually workingThis includes:-Agentic workflows (reason → decide → act → evaluate)-Cross-product context (jobs, customers, payments, communication)-Reliability, safety, and failure modes-Developer experience for building on top of AI systemsTeam Structure-~30 engineers across 4-6 teams-4-6 EMs / Sr EMs reporting into you-Close partnership with Product, Design, DataWHAT “POSITIVE” LOOKS LIKENot “we shipped AI features.”Instead:-The system proactively recommends and takes actions-Teams build on shared AI primitives, not reinventing them-AI output is reliable, measurable, and improving over time-Engineers trust the system, and move faster because of it-Customers feel like the product is working for them,



not just respondingTHE AI BAR (THIS ROLE IS DIFFERENT)We are not looking for:-Someone who rolled out Copilot internally-Someone who used LLM APIs for features-Someone adjacent to AIWe are looking for someone who has:Built real systems where AI makes decisions and takes actions in production.
That means experience with:-Agent orchestration (not just prompts)-Tool use and workflow execution-Evaluation (offline + online)-Observability and failure handling-Guardrails and safety in real systems-Tradeoffs between autonomy vs. WHAT YOU’LL ACTUALLY DO-Define how AI should work across Jobber, not just within a team-Build and evolve a multi-team org to execute on that vision-Make tradeoffs between speed, quality, and safety-Push teams beyond feature thinking into system thinking-Challenge assumptions, including leadership’s-Drive adoption across engineering, product, and the companyWHAT WE’RE LOOKING FORLeadershipYou’ve led orgs through complexity, not just growth.-Managed managers across multiple teams-Built organizations that scale (not just teams that ship)-Driven cross-org alignment in ambiguous spacesProduct + Systems ThinkingYou think in systems, not features.-You understand how user workflows connect end-to-end-You’ve partnered deeply with Product and Design-You care about customer outcomes, not just technical outputAI Depth (non-negotiable)You’ve built or led production LLM/agentic systems.-You’ve balanced shipping vs infrastructure vs tech debt-You know when to iterate and when to redesignWHY JOBBER
· WHY NOW?This is not “AI theatre.”We already have:-AI Receptionist (live, handling real customer calls)-AI features embedded across the product-250,000+ businesses using the platformWhat we don’t have yet is: This role has a minimum annual salary of $221,800 CAD, a midpoint of $261,000 CAD, and a maximum salary of $300,100 CAD, designed to reflect the progression from learning the ropes to truly excelling.
We design our compensation to reflect each new hire’s skills, experience, and t

📌 Director, Software Engineering (Winnipeg)
🏢 Devconnectplatform
📍 Winnipeg