Director, Software Engineering (AI Workflows & Ecosystem)

ogether 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, , invoice, and collect from their customers while providing an easy and professional customer experience. Running a small 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 want! THE 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 next The platform doesn’t proactively help them run their . That’s the gap. The opportunity is to evolve Jobber from: AI-powered features → AI-powered workflows → AI-powered operations This 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, , and follow-ups They’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 that remove 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 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 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 working This includes: Agentic workflows (reason → decide → act → evaluate)Cross-product context (jobs, customers, , communication)Reliability, safety, and failure modesDeveloper experience for building on top of AI systems Team Structure ~30 engineers across 4–6 teams4–6 EMs / Sr EMs reporting into youClose partnership with Product, Design, Data WHAT “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 responding THE 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 AI We 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. control You don’t need to code daily, but you must be able to reason at the system level. WHAT YOU’LL ACTUALLY DO Define 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 company 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 spaces Product + 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 output AI Depth (non-negotiable) You’ve built or led production LLM/agentic systems. You understand what actually works (and what doesn’t)You’ve seen systems fail and improved themYou have opinions about evaluation, reliability, and safety Execution You can move fast without breaking everything. You’ve balanced shipping vs infrastructure vs tech debtYou know when to iterate and when to redesign WHY JOBBER · WHY NOW? This is not “AI theatre.” We already have: AI Receptionist (live, handling real customer calls)AI features embedded across the product250,000+ businesses using the platform What we don’t have yet is: A unified, intelligent system across the product. That’s what this role builds. TLDR: Most Director roles optimize delivery. This one defines: How an entire product becomes intelligent. What you can expect from Jobber: A total compensation package that includes an extended health benefits package with fully paid premiums for both body and mind, matching in RRSP, TFSA or FHSA, and stock options.A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential.A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.To work with a group of people who are humble, supportive, and give a sh*t about our customers. We believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process. A bit more about us Job by job, we’re transforming the way service is delivered. Your lawn care provider, home cleaning service, plumber or painter could use Jobber to better connect with their customers, save time in the office, invoice faster, and get paid! We’re bringing tens of thousands of people together with technology to deliver billions of dollars a year in services to happy customers. Jobber exists to help make these small businesses successful, and when they’re successful we all win! Skills: Software Engineering