Director of Software Engineering, Jobber

AI Workflows & Ecosystem

CA$221.8-300.1k

+ Stock options. This role has a midpoint of $261,000 CAD. 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

Senior and Expert level

Toronto

Vancouver

More information about location

1+ day a week in office

Job tracking and customer management software for home service businesses

Be an early applicant

Job tracking and customer management software for home service businesses

1001+ employees

B2BCommunicationCustomer serviceFinancial ServicesSaaSMobile

Be an early applicant

CA$221.8-300.1k

Senior and Expert level

Toronto

Vancouver

More information about location

1+ day a week in office

1001+ employees

B2BCommunicationCustomer serviceFinancial ServicesSaaSMobile

Company mission

To help home service professionals around the world win.

Job

Company

Role

Who you are

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
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

What the job involves

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
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
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)
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
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

Our take

For businesses that sell home services, it can be difficult keeping up with paperwork, scheduling appointments, and chasing payments, especially when their teams are small. Jobber delivers a comprehensive toolbox to keep track of all these aspects, so that small business owners can concentrate on more important things like serving their customers and building their brand.

Jobber was founded in 2011, initially to help a friend who owned a small painting business. The founders quickly discovered that what they were building could help many more owners across a number of industries, going on to launch the product which is now used by over 300,000 home service professionals in over 60 countries.

What makes Jobber stand out is that it collects all the vital parts of running a home services business into one place, removing the burden of keeping track of multiple sources of information. The company has seen significant funding which it has invested in R&D and growing its customer base, and boasts four consecutive years on The Globe and Mail's Canada's Top Growing Companies List.

Steph

Company Specialist at Welcome to the Jungle

Insights

Top investors

15% employee growth in 12 months

Glassdoor (3.9)

Company

Funding (last 2 of 7 rounds)

Jan 2023

$100m

SERIES D

Jan 2021

$60m

GROWTH EQUITY VC

Total funding: $185.8m

Company HQ

Downtown, Edmonton, AB

Leadership

Sam Pillar

(Co-Founder & CEO)

Prior to co-founding Jobber in 2011, Sam was a Freelance Software Developer at Cardboard Creative and a Business Analyst/Management Consultant at CGI.

Forrest Zeisler

(Co-Founder & CTO)

Experienced Developer, with a degree in Engineering from the University of Alberta.

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