--- title: 'Director, Software Engineering (AI Workflows & Ecosystem) at Jobber' canonical: 'https://feeny.ai/job/director-software-engineering-ai-workflows-ecosystem-jobber-remote-bzsc3b3qacj5' type: 'job' last_seen: '2026-09-26' --- # Director, Software Engineering (AI Workflows & Ecosystem) at Jobber - **Company:** Jobber - **Location:** Remote - **Compensation:** $222k–$300k - **Employment:** full-time - **Work type:** remote - **Posted:** 2026-09-24 - **Last confirmed live:** 2026-09-26 - **Apply:** https://jobs.ashbyhq.com/jobber/850af5d5-0d94-4b9d-9dda-5833530dd6d8/application **Skills:** LLM, Agentic systems, Workflow orchestration, AI evaluation, Observability, System design > Lead the evolution of Jobber's AI system layer from fragmented features to a unified, intelligent platform. Define end-to-end AI governance, orchestration, and decision-making processes across workflows to remove thinking from overwhelmed users and improve customer outcomes. ## Job description 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 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! ## 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 jobs - Piece together context across workflows - Decide what to do next The 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 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 pm - A cleaner managing 30 clients and 5 employees - A landscaper juggling scheduling, payments, 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 system - How context moves across workflows - How 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, payments, communication) - Reliability, safety, and failure modes - Developer experience for building on top of AI systems ## Team Structure - ~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.” 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 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. 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. 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 ## WHAT WE’RE LOOKING FOR Leadership 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 Execution 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 WHY 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 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. Compensation: At Jobber, we also believe that compensation should be transparent, fair, and supportive of your experience and growth. 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 the complexity of the role, ensuring a fair and competitive salary. Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint. The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions, while offers below the midpoint reflect strong potential with room to develop. This approach ensures that compensation aligns with both an individual’s current capabilities and their opportunity for future growth. We believe in transparency and open conversations about compensation. If you have any questions about our approach, we’re happy to discuss them throughout the hiring process! 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! ## About Jobber ## Company Overview - **One-liner**: Jobber provides cloud-based field service management software that helps small home service businesses organize their operations, from quoting and scheduling to invoicing and payment processing. - **Entity Type**: Private (Series D) - **Headquarters**: Edmonton, Alberta, Canada - **Founded**: 2011 - **Founders**: Sam Pillar (CEO) and Forrest Zeisler (CTO) ## Core Business - Primary industry: Field Service Management Software (Vertical SaaS) - Target customers: B2B; small and medium-sized home service businesses (plumbers, electricians, landscapers, cleaners, painters, etc.) - Mission or purpose statement: "To help service pros win" by building software that automates the day-to-day operations of small home service businesses, enabling them to grow and thrive. ## Products & Services - **[Jobber Platform]**: A cloud-based (SaaS) field service management platform that combines CRM, scheduling, dispatching, invoicing, online payments, client communication, and reporting into a single, easy-to-use app. It is designed to replace spreadsheets, pen-and-paper, and disconnected tools for service professionals. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed (conflicting reports suggest a valuation around $1 billion based on the $100M Series D). - **Key Metric**: Total Funding of **$183.5M** (including a $100M Series D led by General Atlantic in February 2023). Annual Revenue estimated at **$100M**. - **Notable Investors/Partners**: General Atlantic (lead), OMERS Ventures, Summit Partners, and others. - **Growth Signals**: Over **400,000 service professionals** use the platform across **60+ countries**. The company has seen **22.6% headcount growth** (YoY, +249 people to 970 employees). It has invoiced over **$40B** in transactions through its platform. ## Competitive Advantages - **Vertical Focus & Depth**: Deeply specialized for home service businesses (plumbers, electricians, landscapers, cleaners), offering a comprehensive, integrated solution that is far more tailored than generic CRM or scheduling tools. - **Platform Stickiness**: By integrating core workflows (quoting, scheduling, invoicing, payments, client management), Jobber becomes the operational backbone for its customers, creating high switching costs. - **Strong Brand & Community**: Recognized as an award-winning, fast-growing Canadian tech company (Deloitte, Fast Company, Globe and Mail). Publishes the "Jobber Home Service Economic Report," positioning itself as a thought leader in the space. - **Large, Engaged User Base**: Over 400,000 pros and 27 million properties served, generating a powerful network effect and data moat. ## Strategic Focus - **AI-Driven Innovation**: Actively hiring for a "Director, Software Engineering (AI Workflows & Ecosystem)" and a "Director, Product Management (Marketing Agent)," indicating a strong push to embed AI into the platform to automate more customer-facing and operational tasks. - **Fintech Expansion**: Building a significant fintech business within the platform (payments, invoicing), with dedicated roles like "VP, Payments and Fintech" and "Payments GTM Operations and Strategy Lead." This is a key revenue and stickiness driver. - **Product-Led Growth (PLG)**: Hiring a "Principal Demand Generation Manager, Product-Led Growth" suggests a focus on scaling user acquisition through the product itself. - **Marketplace & Ecosystem**: Developing an "ISV Marketplace" (via a Senior Partner Program Manager role) to build a third-party ecosystem around the core platform. ## Why Work Here - **Mission-Driven Work**: Employees directly see the impact of their work on real small business owners ("service pros"), helping them build better lives for themselves and their families. - **Strong Culture**: Described as a place for people who "give a shit," are "humble," "supportive," and "think like an entrepreneur." The culture emphasizes ownership, urgency, and collective success over ego. - **Hybrid-First Policy**: Most roles are listed as "Hybrid, Canada" (likely Edmonton) or "Remote, Canada," offering flexibility. A small number of roles are fully remote. - **Growth & Impact**: The company is in a high-growth phase (22.6% headcount growth YoY) with strong funding, offering significant opportunities for career advancement and to work on meaningful problems at scale. - **Strong Talent Pool**: Recruits heavily from other top Canadian tech companies (Shopify, Clio, Vidyard, TouchBistro, FreshBooks), indicating a competitive and respected engineering and product culture. ## Sources 1. [getjobber.com](https://www.getjobber.com/about/) 2. [getjobber.com](https://www.getjobber.com/about/careers/) 3. [getjobber.com](https://www.getjobber.com/about/team/) 4. [linkedin.com](https://ca.linkedin.com/company/jobber-software) 5. 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