Principal Engineer (AI, Office of the CEO)

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.
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. 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. 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. 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.
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.
Own the hard parts of trustworthy AI at company scale: retrieval quality, permissions, security, and reliability.
Work hands-on across the modern AI stack (LLMs, retrieval, agents, integrations) while keeping the foundations deliberately pragmatic.
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.
Work directly with executive leadership: what you build informs how the company makes decisions, every day.
To be successful, you should have:
A track record of building production systems at Staff+ scope: data infrastructure, retrieval, or applied AI used daily by hundreds to thousands of people who depend on it.
Hands-on depth with the modern AI stack, and at least one battle scar from a system that showed you how confidently AI can be wrong.
Pragmatic technology instincts: you reach for proven tools by default and can defend the exceptions.
Founding-engineer, consulting, or forward-deployed experience: comfortable owning outcomes inside someone else's domain.
A daily working relationship with AI tools and agents, as instruments you build with and build for.
The pragmatism to ship every few weeks, the standards to make it trustworthy anyway, and the communication skills to explain both to a CEO.
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.
A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential.
A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.
To work with a group of people who are humble, supportive, and give a sh*t about our customers.
We believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.
A bit more about us:
Job by job, we’re transforming the way service is delivered. Your lawn care provider, home cleaning service, plumber or painter could use Jobber to better connect with their customers, save time in the office, invoice faster, and get paid! We’re bringing tens of thousands of people together with technology to deliver billions of dollars a year in services to happy customers. Jobber exists to help make these small businesses successful, and when they’re successful we all win!

Work arrangement
Yes