Principal Engineer (AI, Office of the CEO)

<p><em><strong>Please note:</strong></em> 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!</p> <ul> <li> <p>This will be updated automatically on all job posts above our <em><strong>What you can expect from Jobber</strong></em> headline.</p> </li> <li> <p>The automated email to candidates will have the same message as above.</p> </li> </ul> <p><strong>Do you want to be the first engineer on something an entire company will run on?</strong></p> <p>Then Jobber might be the place for you! We're looking for a <strong>Principal Software Engineer, AI,</strong> to join the <strong>Office of the CEO</strong>.</p> <p><strong>The team:</strong></p> <p>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.</p> </p> <p><strong>The role:</strong></p> <p>Reporting to the <strong>VP of Customer Experience Innovation</strong>, 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.</p> <p>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.</p> </p> <p>The <strong>Principal Software Engineer, AI</strong> will:</p> <ul> <li> <p>Architect and build new internal AI systems end to end, from first design to production, as the founding engineer.</p> </li> <li> <p>Own the hard parts of trustworthy AI at company scale: retrieval quality, permissions, security, and reliability.</p> </li> <li> <p>Work hands-on across the modern AI stack (LLMs, retrieval, agents, integrations) while keeping the foundations deliberately pragmatic.</p> </li> <li> <p>Embed with teams across the company, working day-to-day with function leaders and their teams