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 “POSITIVE” 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 th

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