jobber - Director, Software Engineering (AI Workflows & Ecosystem)
Requirements
• 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. 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 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 company • You’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 spaces • PRODUCT + SYSTEMS THINKING • You 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 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 them • You have opinions about evaluation, reliability, and safety • You can move fast without breaking everything. • You’ve balanced shipping vs infrastructure vs tech debt • You know when to iterate and when to redesign
Benefits
• “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. • 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 system • How context moves across workflows • How actions get triggered (and when they shouldn’t) • How we evaluate whether AI is actually working • 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 systems • ~30 engineers across 4–6 teams • 4–6 EMs / Sr EMs reporting into you • Close partnership with Product, Design, Data • WHAT “GOOD” LOOKS LIKE • Not “we shipped AI features.” • 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 responding • THE 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 AI • We are looking for someone who has: • Built real systems where AI makes decisions and takes actions in production. • 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 platform • What we don’t have yet is: A unified, intelligent system across the product. • That’s what this role builds. • 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.
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