[All remote jobs](https://jobicy.com/jobs.md)[![Jobber logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/135a74b7-221.jpeg)](https://jobicy.com/company/jobber.md)[Jobber](https://jobicy.com/company/jobber.md) # Principal Engineer (AI, Office of the CEO) Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/jobber.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 229,300–310,200 / yrDepartment[Software Engineering](https://jobicy.com/categories/engineering.md)EmploymentFull TimeExperienceDirectorPublished9 Oct 2026Apply before8 Nov 2026Listing views20Application actions0Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Jobber is hiring a Principal Software Engineer, AI, as the founding technical leader within the Office of the CEO. The role architects and delivers internal AI systems from initial design through production, with responsibility for retrieval quality, permissions, security, reliability, LLMs, agents, and integrations. The engineer will embed with teams across the company, evaluate build-versus-buy options, run rapid proofs of concept, and partner directly with executive leadership. Success requires Staff+ experience delivering production AI, data, or retrieval systems at organizational scale, along with pragmatic technical judgment and exceptional stakeholder communication. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a highly senior founding-engineer role requiring end-to-end ownership of production AI systems in an ambiguous, fast-moving environment. It combines deep technical design, AI trust and security concerns, rapid delivery expectations, and direct executive-level influence. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianMarket rate$269,700US market range$220k–$330k0$363k AI insightThe disclosed annual base-salary range is $229,300 to $310,200 USD, with a stated midpoint of $269,700; therefore, the job median is $269,700. For a US-based principal applied-AI/software engineering role with Staff+ scope and executive-facing ownership, an estimated market base-salary range is $220,000 to $330,000 annually. Equity, benefits, and stipends are separate from the disclosed base salary and are not included in these figures. ## Core skills Skills and capabilities most closely associated with this opportunity. [Applied AI](https://jobicy.com/jobs?search_keywords=Applied%20AI.md)[LLMs](https://jobicy.com/jobs?search_keywords=LLMs.md)[Retrieval-Augmented Generation](https://jobicy.com/jobs?search_keywords=Retrieval-Augmented%20Generation.md)[AI Agents](https://jobicy.com/jobs?search_keywords=AI%20Agents.md)[Software Architecture](https://jobicy.com/jobs?search_keywords=Software%20Architecture.md)[Data Infrastructure](https://jobicy.com/jobs?search_keywords=Data%20Infrastructure.md)[Security and Permissions](https://jobicy.com/jobs?search_keywords=Security%20and%20Permissions.md)[Systems Reliability](https://jobicy.com/jobs?search_keywords=Systems%20Reliability.md)[Technical Leadership](https://jobicy.com/jobs?search_keywords=Technical%20Leadership.md)[Executive Stakeholder Management](https://jobicy.com/jobs?search_keywords=Executive%20Stakeholder%20Management.md) Sample interview questionsDescribe a production AI or data system you built that was used by hundreds or thousands of people. What were the key architectural decisions?I would outline the user problem, system scale, architecture, operational requirements, and measurable outcome. I would emphasize decisions around data quality, observability, access control, cost, latency, reliability, and how I iterated after real user feedback. How would you design a trustworthy internal retrieval and agent system that can access company knowledge while enforcing permissions? I would begin with an identity-aware data model and source-level access controls, then enforce authorization both during retrieval and before tool execution. I would add source attribution, evaluation datasets, audit logs, monitoring for unsafe or low-confidence behavior, and staged rollout procedures to validate quality before broad deployment. Tell us about a time an AI system produced a confident but incorrect result. How did you address it? I would explain the failure mode, how it was detected, its user impact, and the corrective actions taken. A strong response would include improving retrieval or grounding, adding evaluations and guardrails, exposing citations or uncertainty where appropriate, and monitoring recurrence in production. How do you decide whether to build a capability internally, buy a product, or integrate a third-party platform? I evaluate strategic differentiation, time to value, total cost of ownership, security and compliance, vendor lock-in, integration complexity, operational burden, and the reversibility of the decision. I favor a short, measurable proof of concept when uncertainty is high and make explicit criteria for scaling, buying, or stopping. How would you communicate a technical AI risk or tradeoff to the CEO and functional leaders? I would frame the issue in terms of business impact, likelihood, affected users, available options, cost, and decision needed. I would avoid unnecessary jargon, state my recommendation clearly, and provide enough technical detail and evidence for stakeholders to understand the risk and approve an appropriate path forward. Opportunity details ## About this role. 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. * 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. 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. Compensation: At Jobber, we believe that compensation should be transparent, fair, and supportive of your experience and growth. This role has a minimum annual salary of $229,300, a midpoint of $269,700, and a maximum salary of $310,200, designed to reflect the progression from learning the ropes to truly excelling. We design our compensation to reflect each new hire’s skills, experience, and the complexity of the role, ensuring a fair and competitive salary. Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint. The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions, while offers below the midpoint reflect strong potential with room to develop. This approach ensures that compensation aligns with both an individual’s current capabilities and their opportunity for future growth. 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. Your professional growth matters to us too! You’ll have access to a dedicated talent development program that includes career coaching and opportunities for career development. We believe in transparency and open conversations about compensation. If you have any questions about our approach, we’re happy to discuss them throughout the hiring process! 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! Show more [Apply now >](https://jobicy.com/jobs/154935-principal-engineer-ai-office-of-the-ceo.md) * ![Upload CV](data:image/svg+xml;base64,PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHdpZHRoPSI2NSIgaGVpZ2h0PSI2NSIgZmlsbD0ibm9uZSIgeG1sbnM6dj0iaHR0cHM6Ly92ZWN0YS5pby9uYW5vIj48ZyBjbGlwLXBhdGg9InVybCgjQSkiPjxwYXRoIGQ9Ik0wIDBINjVWNjVIMFYwWiIgZmlsbD0iIzAyOWFlYiIvPjxnIGZpbGw9IiNmZmYiIHN0cm9rZT0iI2ZmZiIgc3Ryb2tlLXdpZHRoPSIyIj48cGF0aCBkPSJNMzMuMDQ5IDE1LjQ1NGExLjQzIDEuNDMgMCAwIDAtMi4wOTcgMGwtNy41NzkgOC4xNDdhMS4zOCAxLjM4IDAgMCAwIC4wOSAxLjk3MyAxLjQ0IDEuNDQgMCAwIDAgMi4wMDgtLjA4OGw1LjEwOS01LjQ5MnYyMC42MWExLjQxIDEuNDEgMCAwIDAgMS40MjEgMS4zOTdjLjc4NSAwIDEuNDIxLS42MjUgMS40MjEtMS4zOTd2LTIwLjYxbDUuMTA5IDUuNDkyYTEuNDQgMS40NCAwIDAgMCAyLjAwOC4wODggMS4zOCAxLjM4IDAgMCAwIC4wOS0xLjk3M2wtNy41NzktOC4xNDZ6TTE2Ljc2OSAzOC40YzAtLjc3My0uNjItMS40LTEuMzg1LTEuNFMxNCAzNy42MjcgMTQgMzguNHYuMTAybC4yMTUgNi4yMjljLjIyMyAxLjY4LjcwMSAzLjA5NSAxLjgxMyA0LjIxOHMyLjUxIDEuNjA3IDQuMTcyIDEuODMzYzEuNi4yMTggMy42MzYuMjE4IDYuMTYuMjE4aDExLjI4bDYuMTYtLjIxOGMxLjY2Mi0uMjI2IDMuMDYxLS43MDkgNC4xNzItMS44MzNzMS41ODktMi41MzggMS44MTMtNC4yMThDNTAgNDMuMTEzIDUwIDQxLjA1NSA1MCAzOC41MDNWMzguNGMwLS43NzMtLjYyLTEuNC0xLjM4NS0xLjRzLTEuMzg1LjYyNy0xLjM4NSAxLjRsLS4xOSA1Ljk1OGMtLjE4MiAxLjM3LS41MTUgMi4wOTUtMS4wMjYgMi42MTJzLTEuMjI4Ljg1My0yLjU4MyAxLjAzOGMtMS4zOTUuMTktMy4yNDMuMTkzLTUuODkzLjE5M0gyNi40NjJjLTIuNjUgMC00LjQ5OC0uMDAzLTUuODkzLS4xOTMtMS4zNTUtLjE4NC0yLjA3Mi0uNTIxLTIuNTgzLTEuMDM4cy0uODQ0LTEuMjQyLTEuMDI2LTIuNjEyYy0uMTg3LTEuNDEtLjE5MS0zLjI3OS0uMTkxLTUuOTU4eiIvPjwvZz48L2c+PGRlZnM+PGNsaXBQYXRoIGlkPSJBIj48cGF0aCBmaWxsPSIjZmZmIiBkPSJNMCAwaDY1djY1SDB6Ii8+PC9jbGlwUGF0aD48L2RlZnM+PC9zdmc+) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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