Are 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 skilled 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. That’s why we put the power and flexibility in their hands to run their businesses how, where, and when they wantTHE PROBLEM YOU’D OWN
Jobber 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. But today, those systems are still fragmented. Some teams are ahead. Others aren’t. Some workflows are intelligent. Others are still manual. And most importantly, the system doesn’t yet think across the product.
A service pro still has to:Manually follow up on jobsPiece together context across workflowsDecide what to do nextThe platform doesn’t proactively help them run their business. That’s the gap.
The opportunity is to evolve Jobber from:AI-powered features → AI-powered workflows → AI-powered business operationsThis role owns that shift. Not a team. Not a feature.
The system.
THE CUSTOMER
You’re building for people who don’t have time to think about software.
A plumber finishing their last job at 6 pmA cleaner managing 30 clients and 5 employeesA landscaper juggling scheduling, payments,



and follow-upsThey’re not asking for “AI.” They’re asking:“What should I do next?”“Why didn’t this job convert?”“Who should I follow up with today?”And eventually:They shouldn’t have to ask at all.
The Director who succeeds here will understand:
This isn’t about building clever systems; it’s about building systems thatremove thinking from already overwhelmed people.
WHAT YOU’D OWN
End-to-end ownership of Jobber’s AI system layer. You’re not owning a single team. You’re owning how intelligence flows across the entire product.
Product + Platform ScopeAI 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 means
You are responsible for:How decisions get made inside the systemHow context moves across workflowsHow 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 modesDeveloper experience for building on top of AI systemsTeam Structure~30 engineers across 4–6 teams4–6 EMs / Sr EMs reporting into youClose partnership with Product, Design, DataWHAT “GOOD” LOOKS LIKE




Not “we shipped AI features.”Instead:The system proactively recommends and takes actionsTeams build on shared AI primitives, not reinventing themAI output is reliable, measurable, and improving over timeEngineers trust the system, and move faster because of itCustomers 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 internallySomeone who used LLM APIs for featuresSomeone 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 executionEvaluation (offline + online)Observability and failure handlingGuardrails and safety in real systemsTradeoffs between autonomy vs. controlYou don’t need to code daily, but you must be able toreason at the system level.
WHAT YOU’LL ACTUALLY DODefine how AI should work across Jobber, not just within a teamBuild and evolve a multi-team org to execute on that visionMake tradeoffs between speed, quality, and safetyPush teams beyond feature thinking into system thinkingChallenge assumptions, including leadership’sDrive adoption across engineering, product, and the companyWHAT WE’RE LOOKING FOR
Leadership
You’ve led orgs through complexity, not just growth.
Managed managers across multiple teamsBuilt organizations that scale (not just teams that ship)Driven cross-org alignment in ambiguous spacesProduct + Systems Thinking
You think in systems, not features.
You understand how user workflows connect end-to-endYou’ve partnered deeply with Product and DesignYou care about customer outcomes, not just technical outputAI Depth (non-negotiable)
You’ve built or ledproduction LLM/agentic systems.
You understand what actually works (and w

📌 Director, software engineering – ai workflows, ecosystem (Winnipeg)
🏢 Jobber
📍 Winnipeg