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Salary: USD 229,300 - 310,200 / annual
Jobber is seeking a Principal Software Engineer, AI to join the Office of the CEO as the founding technical leader for a new internal AI initiative. This is a startup-within-a-startup role with a mandate to reinvent how a 1,000-person company operates in the AI era.
You will be the first engineer on this team, reporting to the VP of Customer Experience Innovation. The role combines architectural leadership with hands-on building: you'll design and ship new AI systems end-to-end, from conception to production, while owning the hard problems of trustworthy AI at scale—retrieval quality, permissions, security, and reliability.
Key responsibilities include:
- Architecting and building internal AI systems end-to-end as the founding engineer
- Owning trust, permissions, security, and reliability challenges for AI systems at company scale
- Working hands-on across the modern AI stack (LLMs, retrieval, agents, integrations) with pragmatic technology choices
- Embedding with teams across Jobber's functions, shipping AI into real workflows and building systems that outlast your involvement
- Running build-vs-buy evaluations and fast POCs with judgment to commit hard and kill fast
- Working directly with executive leadership; your work informs daily company decision-making
This is a builder's role with unusual range. One week you're designing novel system architecture; the next you're embedded with a team shipping working AI into their workflow. You'll set technical standards for all AI work at Jobber and work with minimal bureaucracy—no layers between you and decision-makers, no roadmap theater.
Jobber is a B2B SaaS platform helping service businesses (lawn care, plumbing, cleaning, painting, etc.) connect with customers, save time, invoice faster, and get paid. The company operates in a $400-billion industry with no dominant player.
REQUIREMENTS:
- Track record of building production systems at Staff+ scope: data infrastructure, retrieval, or applied AI used daily by hundreds to thousands of people
- Hands-on depth with the modern AI stack and at least one battle scar from a system that showed how confidently AI can be wrong
- Pragmatic technology instincts: reach for proven tools by default and can defend exceptions
- Founding-engineer, consulting, or forward-deployed experience; comfortable owning outcomes inside someone else's domain
- Daily working relationship with AI tools and agents as instruments you build with and build for
- Pragmatism to ship every few weeks, standards to make it trustworthy, and communication skills to explain both to a CEO
