Director, Software Engineering (AI Workflows & Ecosystem)

About Jobber

Jobber exists to help small businesses succeed. We partner with small home service businesses—like plumbers, painters, and landscapers—to revolutionize service delivery through technology. Our platform enables them to quote, schedule, invoice, and collect payments seamlessly, providing a professional customer experience. As technology evolves and customer expectations rise, Jobber empowers these businesses with the flexibility to operate how, where, and when they choose.

The Opportunity: Owning the AI System

Jobber has AI in production, but not yet at its full potential. While AI already assists with calls, drafts responses, and powers product features, these systems are fragmented. Some teams are advanced, others less so; some workflows are intelligent, others manual. Crucially, the system doesn't yet think across the entire product. Service professionals still manually follow up on jobs, piece together context, and decide next steps – the platform isn't proactively helping them run their business. This role owns the critical shift from AI-powered features → AI-powered workflows → AI-powered business operations, taking ownership of the entire AI system, not just a team or feature.

Building for the Customer

You'll be 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, or a landscaper juggling scheduling, payments, and follow-ups. They aren't asking for “AI”; they're asking, “What should I do next?”, “Why didn’t this job convert?”, or “Who should I follow up with today?” Ultimately, they shouldn't have to ask at all. The successful Director will understand that this role 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, focusing on how intelligence flows across the entire product.

Product + Platform Scope

• AI Foundations (models, orchestration, evaluations, 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 are made within the system
• How context moves across workflows
• How actions are triggered (and when they should not be)
• How we evaluate if 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

• Approximately 30 engineers across 4–6 teams
• 4–6 Engineering Managers / Senior Engineering Managers reporting directly to you
• Close partnership with Product, Design, and Data teams

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
• Used LLM APIs for features
• Was 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, beyond individual teams
• Build and evolve a multi-team organization 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 AI adoption across engineering, product, and the company

What We're Looking For

Leadership

You’ve led organizations 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.

• Understand how user workflows connect end-to-end
• Partnered deeply with Product and Design
• Care about customer outcomes, not just technical output

AI Depth (Non-negotiable)

You’ve built or led production LLM/agentic systems.

• Understand what actually works (and what doesn’t)
• Seen systems fail and improved them
• Have opinions about evaluation, reliability, and safety

Execution

You can move fast without breaking everything.

• Balanced shipping vs. infrastructure vs. tech debt
• 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 believe compensation should be transparent, fair, and supportive of your experience and growth. This role has an annual salary range of $221,800 CAD (minimum), $261,000 CAD (midpoint), and $300,100 CAD (maximum). Our compensation is designed to reflect skills, experience, and role complexity, ensuring competitive salaries. The range supports growth, with established hires typically starting around the midpoint. The higher end is for deep expertise and lasting contributions, while offers below midpoint reflect strong potential with room to develop. We encourage open conversations about compensation throughout the hiring process.

Benefits & Perks

• A total compensation package including an extended health benefits package with fully paid premiums for both body and mind.
• Matching contributions to RRSP, TFSA, or FHSA.
• Stock options.
• A dedicated Talent Development team and access to coaching, learning, and leadership programs to foster career growth and potential.
• A unique opportunity to build, grow, and impact a $400-billion industry with no dominant player... yet.
• Work with a team that is humble, supportive, and deeply cares about our customers.

Diversity & Inclusion

We believe diverse teams perform better and that fostering an inclusive work environment is key to growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer and committed to working with applicants requesting accommodation at any stage of the hiring process.

About Us

Job by job, we’re transforming how service is delivered. Your lawn care provider, home cleaning service, plumber, or painter could be using Jobber to better connect with customers, save time, invoice faster, and get paid. We bring 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!