Latest AI JobsBrowse Jobs
jobber logo

Principal Engineer (AI, Office of the CEO)

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

About this role

This remote Principal Engineer role suits an experienced technologist who wants to build foundational internal AI systems as the first technical member of a startup team inside Jobber. The position reports to the VP of Customer Experience Innovation and operates within the Office of the CEO to shape how a large organization runs.

Role Overview

The Principal Software Engineer, AI joins a small, senior team tasked with reinventing operational workflows across Jobber. The position acts as the founding technical seat to architect, build, and deploy new AI systems from zero to production. The work directly impacts all business functions, collaborating closely with department leaders and executive leadership with minimal bureaucracy.

Key Responsibilities

Architect and build internal AI systems end-to-end from initial design to production deployment as the founding engineer.
Address challenges related to trustworthy AI at scale, including retrieval quality, security, permissions, and reliability.
Work hands-on with LLMs, retrieval systems, agents, and integrations while maintaining pragmatic technical foundations.
Embed with various teams to integrate AI into real workflows and establish self-sustaining systems.
Evaluate build-versus-buy options and execute fast proofs of concept with decisive judgment.
Collaborate daily with executive leadership to inform company-wide decision-making through technical delivery.

Requirements

Demonstrated background in building production systems at a Staff level or higher, such as data infrastructure, retrieval tools, or applied AI used by hundreds or thousands of people.
Hands-on experience with the modern AI stack and familiarity with the failure modes of AI systems.
Pragmatic technology approach favoring proven tools by default.
Prior founding engineer, consulting, or forward-deployed experience.
Regular working familiarity with AI tools and agents as construction instruments.
Capacity to ship increments frequently while maintaining quality and communicating effectively with leadership.

Skills and Tools

LLMs
Retrieval systems
AI agents
Modern software integrations and data infrastructure

Salary and Benefits

Minimum annual salary of $196,300, a midpoint of $230,900, and a maximum of $265,600, depending on experience and role complexity.
Total compensation package including equity rewards and stock options.
Extended health benefits package with fully paid premiums.
Retirement savings matching options including RRSP, TFSA, or FHSA.
Annual stipends for health and wellness.
Access to a dedicated Talent Development team providing career coaching and leadership programs.

About the Company

Jobber provides technology that connects small businesses, such as home cleaning services, lawn care providers, plumbers, and painters, with their customers to save office time, invoice faster, and facilitate payments. The company unites tens of thousands of people to deliver billions of dollars in services annually to help small businesses succeed.

How to Apply

Interested candidates should apply directly on the official Jobber careers page.

Skills and tech stack

Questions candidates ask

Where is the position located?

The position is remote.

Who does the role report to?

The role reports to the VP of Customer Experience Innovation.

What is the salary range for this role?

The minimum annual salary is $196,300, the midpoint is $230,900, and the maximum salary is $265,600.

What team does this role belong to?

The role belongs to a startup team inside Jobber located in the Office of the CEO.

What benefits are included besides base salary?

Benefits include equity rewards, stock options, extended health benefits with fully paid premiums, retirement savings matching for RRSP, TFSA, or FHSA, wellness stipends, and access to career coaching and talent development programs.

Ready to apply?

The application is on the official jobber careers page.

Apply on company site