Director of Software Engineering, Jobber
AI Workflows & Ecosystem
+ Stock options
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
Be an early applicant
+ Stock options
1001+ employees
Company mission
To help home service professionals around the world win.
Role
Who you are
- 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
- Built real systems where AI makes decisions and takes actions in production
- 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
- 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
- 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
- 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
- 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 to keep 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 several 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
15% employee growth in 12 months
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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