Principal Engineer (AI, Office of the CEO)

Job Overview

Please note: Our Talent team at Jobber will be offline for Jobber Impact - our flagship event of the year, bringing Jobberinos together to connect, learn, and celebrate what we're building - starting October 6th and extending until October 9th.

We’ll be back to go through applications and reach out with an update on your candidacy once we return next week! This will be updated automatically on all job posts above our What you can expect from Jobber headline.

Job Description

The automated email to candidates will have the same message as above. Do you want to be the first engineer on something an entire company will run on? Then Jobber might be the place for you!

We're looking for a Principal Software Engineer, AI, to join the Office of the CEO . The team: This is a startup inside Jobber.

A small, senior team in the Office of the CEO with a mandate to reinvent how a 1,000-person company operates in the AI era, and the backing to actually do it. No layers between you and the decision-makers, no roadmap theater, no waiting for alignment.

We ship something real every few hours, learn from it, and compound. The work touches every function at Jobber, and what we build becomes how the company thinks and moves.

This is a builder's role with unusual range. One week you're designing the architecture of a system nobody at Jobber has built before; the next you're embedded with a team, shipping working AI into their real workflow and making them the hero.

We're looking for someone who has shipped production AI or data systems, defaults to pragmatic technology choices, and wants founding-engineer ownership with a real company's resources behind it.

Key Responsibilities

• Please note: Our Talent team at Jobber will be offline for Jobber Impact - our flagship event of the year, bringing Jobberinos together to connect, learn, and celebrate what we're building - starting October 6th and extending until October 9th.
• The work touches every function at Jobber, and what we build becomes how the company thinks and moves.
• The role: Reporting to the VP of Customer Experience Innovation , the Principal Software Engineer will be the founding technical seat: you'll architect and build new AI systems from zero to production, and own the hard problems that come with putting AI at the center of how a company runs - trust, permissions, security, and quality at scale.
• This is a builder's role with unusual range.
• You'll make fast build-vs-buy calls, run POCs and kill them without sentiment, and set the technical standards that everything AI at Jobber gets held to.
• The Principal Software Engineer, AI will: Architect and build new internal AI systems end to end, from first design to production, as the founding engineer.
• Embed with teams across the company, working day-to-day with function leaders and their teams and weekly with executive leadership, shipping AI into real workflows and leaving behind systems and owners that outlast the visit.
• Drive build-vs-buy evaluations and fast POCs, with the judgment to commit hard and kill fast.

Required Skills and Qualifications

• The role: Reporting to the VP of Customer Experience Innovation , the Principal Software Engineer will be the founding technical seat: you'll architect and build new AI systems from zero to production, and own the hard problems that come with putting AI at the center of how a company runs - trust, permissions, security, and quality at scale.
• Founding-engineer, consulting, or forward-deployed experience: comfortable owning outcomes inside someone else's domain.
• The pragmatism to ship every few weeks, the standards to make it trustworthy anyway, and the communication skills to explain both to a CEO.
• Compensation: At Jobber, we believe that compensation should be transparent, fair, and supportive of your experience and growth.
• We design our compensation to reflect each new hire's skills, experience, and the complexity of the role, ensuring a fair and competitive salary.
• We welcome people of diverse backgrounds, experiences, and perspectives.

Benefits and Perks

• Base salary is just one part of a total compensation package that will include equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums for body and mind.
• What you can expect from Jobber: 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.

Work Location and Schedule

This role is listed as Remote USA with location information shown as Remote USA. The employment type is Full Time.

About the Company

Jobber is the organization connected with this listing. USA Jobs Today displays this opportunity for job discovery only, so applicants should verify company details, application instructions, and eligibility on the official employer website.