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 qualified 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. 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.

The platform doesn’t proactively help them run their business. AI-powered features → AI-powered workflows → AI-powered business operations This role owns that shift. THE CUSTOMER

You’re building for people who don’t have time to think about software. They’re not asking for “AI.” This isn’t about building clever systems; it’s about building systems that End-to-end ownership of Jobber’s AI system layer. You’re owning how intelligence flows across the entire product.

AI Foundations (models, orchestration, evals, guardrails) Copilot (user-facing intelligence layer) Emerging surfaces (voice, messaging, cross-product intelligence) How we evaluate whether AI is actually working Cross-product context (jobs, customers, payments, communication) Developer experience for building on top of AI systems Close partnership with Product, Design, Data Not “we shipped AI features.” Teams build on shared AI primitives, not reinventing them AI output is reliable, measurable, and improving over time Customers feel like the product is working for them, not just responding THE AI BAR (THIS ROLE IS DIFFERENT)





Someone adjacent to AI Built real systems where AI makes decisions and takes actions in production. Evaluation (offline + online) control Define how AI should work across Jobber, not just within a team Make tradeoffs between speed, quality, and safety Drive adoption across engineering, product, and the company Built organizations that scale (not just teams that ship) You care about customer outcomes, not just technical output AI Depth (non-negotiable)

You’ve balanced shipping vs infrastructure vs tech debt This is not “AI theatre.” AI Receptionist (live, handling real customer calls) AI features embedded across the product 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.

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. To work with a group of people who are humble, supportive, and give a sh*t about our customers. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.

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! #

📌 Director, Software Engineering - AI Workflows, Ecosystem (Winnipeg)
🏢 Jobber
📍 Winnipeg