[Hiring] Director, Software Engineering (AI Workflows & Ecosystem) @Jobber

Role Description

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.

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. 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 6pm
• A cleaner managing 30 clients and 5 employees
• A landscaper juggling scheduling, payments, and follow-ups

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.

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

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
• Customers feel like the product is working for them, not just responding

Qualifications

• Leadership: 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.
• Product + Systems Thinking: You think in systems, not features.
• AI Depth (non-negotiable): You’ve built or led production LLM/agentic systems.
• Execution: You can move fast without breaking everything.

Requirements

• Built real systems where AI makes decisions and takes actions in production.
• 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.

Benefits

• 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.
• A unique opportunity to build, grow, and leave your impact on a $400-billion industry.
• Work with a group of people who are humble, supportive, and care about customers.
• Commitment to fostering an inclusive work environment.