Director, Software Engineering (AI Workflows & Ecosystem)

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.

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)

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

~30 engineers across 4–6 teams

4–6 EMs / Sr EMs reporting into you

Close partnership with Product, Design, Data

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

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:

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.

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

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

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

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

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

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.

Most Director roles optimize delivery. This one defines: How an entire product becomes intelligent.

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.

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!