Director, Software Engineering (AI Workflows & Ecosystem)

Jobber

1d • $221,800 - $300,100

About The Position

Jobber is seeking a Director of Software Engineering to own the end-to-end AI system layer, evolving the product from AI-powered features to AI-powered workflows and business operations. This role is crucial for integrating AI across the entire product, ensuring intelligence flows seamlessly and proactively assists service professionals. The ideal candidate will build and lead a multi-team organization (~30 engineers) focused on AI foundations, Copilot, automations, and emerging AI surfaces. The goal is to remove thinking from overwhelmed users by creating systems that proactively recommend and take actions, enabling teams to build on shared AI primitives and improving the reliability and measurability of AI output. This is a unique opportunity to define how an entire product becomes intelligent in a rapidly growing market.

Requirements

• Experience leading organizations through complexity, not just growth.
• Managed managers across multiple teams.
• Built organizations that scale.
• Driven cross-org alignment in ambiguous spaces.
• Systems thinking, not just feature thinking.
• Understanding of how user workflows connect end-to-end.
• Deep partnership with Product and Design.
• Care about customer outcomes, not just technical output.
• Experience building or leading production LLM/agentic systems.
• Understanding of what actually works (and what doesn’t) in AI systems.
• Experience with systems failing and improving them.
• Opinions about evaluation, reliability, and safety in AI.
• Ability to move fast without breaking everything.
• Experience balancing shipping, infrastructure, and tech debt.
• Knowledge of when to iterate and when to redesign.
• Experience with agent orchestration (not just prompts).
• Experience with tool use and workflow execution.
• Experience with evaluation (offline + online).
• Experience with observability and failure handling.
• Experience with guardrails and safety in real systems.
• Understanding of tradeoffs between autonomy vs. control.
• Ability to reason at the system level (coding daily not required).

Nice To Haves

• Experience rolling out Copilot internally.
• Experience using LLM APIs for features.
• Experience adjacent to AI.

Responsibilities

• End-to-end ownership of Jobber’s AI system layer, ensuring intelligence flows across the entire product.
• Owning AI Foundations (models, orchestration, evals, guardrails).
• Owning Copilot (user-facing intelligence layer).
• Owning Automations (workflow execution layer).
• Owning Platform Experience / Marketplace (integration + ecosystem surface).
• Owning Emerging surfaces (voice, messaging, cross-product intelligence).
• Defining how decisions are made within the system.
• Ensuring context moves across workflows.
• Defining how actions are triggered and when they shouldn’t be.
• Establishing methods for evaluating AI effectiveness.
• Implementing agentic workflows (reason → decide → act → evaluate).
• Developing cross-product context (jobs, customers, payments, communication).
• Ensuring reliability, safety, and understanding failure modes.
• Improving developer experience for building on top of AI systems.
• Building and evolving a multi-team organization to execute the AI vision.
• Making tradeoffs between speed, quality, and safety.
• Challenging assumptions and driving adoption across engineering, product, and the company.

Benefits

• Extended health benefits package with fully paid premiums for both body and mind.
• Matching in RRSP, TFSA or FHSA.
• Stock options.
• Dedicated Talent Development team.
• Access to coaching, learning, and leadership programs.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees