{"id":26926,"url":"https://alion.io/job/jobber-director-software-engineering-ai-workflows-ecosystem","title":"Director, Software Engineering (AI Workflows & Ecosystem)","company":{"id":7246,"name":"Jobber","domain":"getjobber.com","url":"https://alion.io/company/jobber","size_band":null,"is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Ashby","truth_index":{"grade":"B","score":81,"open_postings":4,"ghost_share":0,"stale_share":0.75,"repost_share":0,"time_to_fill_p50_days":42,"computed_at":"2026-10-19T05:45:15Z"}},"role":"Leadership","role_family":"Leadership","seniority":"head","employment_type":"full_time","work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"board_field","remote_working_hours":null,"hiring_geo_confidence":"inferred","locations":[],"countries":[],"hiring_countries":["US","CA"],"hiring_countries_total":2,"salary":null,"salary_estimate":{"min_usd":227000,"max_usd":410000,"period":"year","method":"role_seniority_country_remote_cell","sample_n":603},"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":true,"technologies":[{"name":"Agentic Workflows","optional":false},{"name":"AI Agents","optional":false},{"name":"Copilot","optional":false},{"name":"Function Calling","optional":false},{"name":"LLM","optional":false},{"name":"LLM Guardrails","optional":false},{"name":"Tool Use","optional":false}],"status":"live","first_seen_at":"2026-07-10T17:01:01Z","employer_posted_date":"2026-07-10","last_verified_at":"2026-10-19T15:14:26Z","board_verified":true,"closed_at":null,"days_open":101,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":101},"description":"Are you driven to bring people, technology, and strategy together to build impactful software?\nJobber 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. That’s why we put the power and flexibility in their hands to run their businesses how, where, and when they want!\nTHE PROBLEM YOU’D OWN\nJobber has AI in production, but not yet at its full potential.\nWe 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.\nA service pro still has to:\nManually follow up on jobs\n\nPiece together context across workflows\n\nDecide what to do next\n\nThe platform doesn’t proactively help them run their business. That’s the gap.\nThe opportunity is to evolve Jobber from: AI-powered features → AI-powered workflows → AI-powered business operations\nThis role owns that shift. Not a team. Not a feature. The system.\nTHE CUSTOMER\nYou’re building for people who don’t have time to think about software.\nA plumber finishing their last job at 6 pm\n\nA cleaner managing 30 clients and 5 employees\n\nA landscaper juggling scheduling, payments, and follow-ups\n\nThey’re not asking for “AI.” They’re asking:\n“What should I do next?”\n\n“Why didn’t this job convert?”\n\n“Who should I follow up with today?”\n\nAnd eventually:\nThey shouldn’t have to ask at all.\n\nThe Director who succeeds here will understand:\nThis isn’t about building clever systems; it’s about building systems that remove thinking from already overwhelmed people.\nWHAT YOU’D OWN\nEnd-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.\nProduct + Platform Scope\nAI Foundations (models, orchestration, evals, guardrails)\n\nCopilot (user-facing intelligence layer)\n\nAutomations (workflow execution layer)\n\nPlatform Experience / Marketplace (integration + ecosystem surface)\n\nEmerging surfaces (voice, messaging, cross-product intelligence)\n\nWhat this actually means\nYou are responsible for:\nHow decisions get made inside the system\n\nHow context moves across workflows\n\nHow actions get triggered (and when they shouldn’t)\n\nHow we evaluate whether AI is actually working\n\nThis includes:\nAgentic workflows (reason → decide → act → evaluate)\n\nCross-product context (jobs, customers, payments, communication)\n\nReliability, safety, and failure modes\n\nDeveloper experience for building on top of AI systems\n\nTeam Structure\n~30 engineers across 4-6 teams\n\n4-6 EMs / Sr EMs reporting into you\n\nClose partnership with Product, Design, Data\n\nWHAT “GOOD” LOOKS LIKE\nNot “we shipped AI features.”\nInstead:\nThe system proactively recommends and takes actions\n\nTeams build on shared AI primitives, not reinventing them\n\nAI output is reliable, measurable, and improving over time\n\nEngineers trust the system, and move faster because of it\n\nCustomers feel like the product is working for them, not just responding\n\nTHE AI BAR (THIS ROLE IS DIFFERENT)\nWe are not looking for:\nSomeone who rolled out Copilot internally\n\nSomeone who used LLM APIs for features\n\nSomeone adjacent to AI\n\nWe are looking for someone who has:\nBuilt real systems where AI makes decisions and takes actions in production.\nThat means experience with:\nAgent orchestration (not just prompts)\n\nTool use and workflow execution\n\nEvaluation (offline + online)\n\nObservability and failure handling\n\nGuardrails and safety in real systems\n\nTradeoffs between autonomy vs. control\n\nYou don’t need to code daily, but you must be able to reason at the system level.\nWHAT YOU’LL ACTUALLY DO\nDefine how AI should work across Jobber, not just within a team\n\nBuild and evolve a multi-team org to execute on that vision\n\nMake tradeoffs between speed, quality, and safety\n\nPush teams beyond feature thinking into system thinking\n\nChallenge assumptions, including leadership’s\n\nDrive adoption across engineering, product, and the company\n\nWHAT WE’RE LOOKING FOR\nLeadership\nYou’ve led orgs through complexity, not just growth.\nManaged managers across multiple teams\n\nBuilt organizations that scale (not just teams that ship)\n\nDriven cross-org alignment in ambiguous spaces\n\nProduct + Systems Thinking\nYou think in systems, not features.\nYou understand how user workflows connect end-to-end\n\nYou’ve partnered deeply with Product and Design\n\nYou care about customer outcomes, not just technical output\n\nAI Depth (non-negotiable)\nYou’ve built or led production LLM/agentic systems.\nYou understand what actually works (and what doesn’t)\n\nYou’ve seen systems fail and improved them\n\nYou have opinions about evaluation, reliability, and safety\n\nExecution\nYou can move fast without breaking everything.\nYou’ve balanced shipping vs infrastructure vs tech debt\n\nYou know when to iterate and when to redesign\n\nWHY JOBBER · WHY NOW?\nThis is not “AI theatre.”\nWe already have:\nAI Receptionist (live, handling real customer calls)\n\nAI features embedded across the product\n\n250,000+ businesses using the platform\n\nWhat we don’t have yet is: A unified, intelligent system across the product.\nThat’s what this role builds.\nTLDR:\nMost Director roles optimize delivery. This one defines: How an entire product becomes intelligent.\nWhat you can expect from Jobber:\nA 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.\n\nA 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.\n\nA unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.\n\nTo work with a group of people who are humble, supportive, and give a sh*t about our customers.\n\nWe 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.\nA bit more about us:\nJob 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. 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