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Principal Engineer (AI, Office of the CEO)

jobberRemoteProduct Engineering
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Salary
Not listed
Job type
Full-time
Work mode
Remote
Experience
Senior
Posted
25 Sept 2026
Status
Open · checked 7d ago

About this role

Principal Engineer (AI, Office of the CEO) is a remote full-time role at Jobber that suits an experienced software engineer looking to build foundational internal AI systems. This position places the right candidate inside a small, senior team tasked with transforming how a large organization operates using artificial intelligence.

Role Overview

Jobber seeks a Principal Software Engineer for artificial intelligence within the Office of the CEO. Reporting to the VP of Customer Experience Innovation, this founding technical role involves designing and implementing production-ready AI systems from the ground up. The work directly influences company-wide decision-making by embedding AI into daily operational workflows.

Key Responsibilities

Architect and build new internal AI systems end to end, from initial design to production deployment.
Manage complex challenges related to trustworthy AI at scale, including retrieval quality, security, permissions, and reliability.
Utilize modern AI technologies such as large language models, retrieval mechanisms, agents, and integrations while maintaining pragmatic foundations.
Collaborate directly with functional leaders and executive management by embedding within teams to integrate AI into real workflows.
Evaluate build-versus-buy options, execute rapid proof-of-concept tests, and make decisions to commit or terminate projects.

Requirements

Demonstrated experience delivering production systems at a Staff level or higher, including data infrastructure, retrieval systems, or applied AI used daily by large groups.
Direct technical familiarity with the modern AI stack and practical experience handling AI system limitations and errors.
Pragmatic approach to technology choices, defaulting to proven tools while justifying exceptions.
Background in founding-engineer, consulting, or forward-deployed roles with ownership of outcomes.
Regular use of AI tools and agents as development instruments and target applications.
Ability to ship frequently while maintaining high standards for trustworthiness and clear communication with executive leadership.

Skills and Tools

LLMs
Retrieval systems
AI agents
Integrations
Data infrastructure

Salary and Benefits

Total compensation package including extended health benefits with fully paid premiums for physical and mental well-being
Retirement and savings account matching options including RRSP, TFSA, or FHSA
Stock options
Access to a Talent Development team, coaching, learning, and leadership programs

About the Company

Jobber provides technology that connects small businesses such as home cleaning services, plumbers, lawn care providers, and painters with their customers. The company focuses on helping service providers save office time, invoice quickly, and manage operations to support billions of dollars in annual services.

How to Apply

Candidates should apply directly on the official Jobber careers page.

Skills and tech stack

LLMsRetrievalAgents

Questions candidates ask

Where is the Principal Engineer (AI, Office of the CEO) role located?

The role is remote.

Who does this position report to?

The position reports to the VP of Customer Experience Innovation.

What level of experience is required for this position?

Candidates must have a track record of building production systems at a Staff-plus scope.

What benefits are included in the compensation package?

Benefits include extended health coverage with fully paid premiums, retirement savings matching options like RRSP, TFSA, or FHSA, and stock options.

Ready to apply?

The application is on the official jobber careers page.

Apply on company site