We're looking for a Principal Software Engineer, AI, to join the Office of the CEO . 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. We ship something real every few hours, learn from it, and compound. 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. 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: 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. 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. The pragmatism to ship every few weeks, the standards to make it trustworthy anyway, and the communication skills to explain both to a CEO. We design our compensation to reflect each new hire's skills, experience, and the complexity of the role, ensuring a fair and market-competitive salary. Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint. 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. 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. To work with a group of people who are humble, supportive, and give a sh*t about our customers. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process. 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 #

📌 Engineering Manager (Canada)
🏢 Avenue.io
📍 Canada