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Salary: USD 196,300 - 265,600 / 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-company with a mandate to reinvent how Jobber's 1,000-person organization operates in the AI era, with direct access to decision-makers and the autonomy to ship real products every few hours.
In this role, you will architect and build new AI systems end-to-end from conception to production, owning the hard problems of trustworthy AI at company scale: retrieval quality, permissions, security, and reliability. You'll work hands-on across the modern AI stack (LLMs, retrieval, agents, integrations) while maintaining pragmatic technology choices. The position combines deep technical ownership with broad organizational impact—one week designing novel system architecture, the next embedded with cross-functional teams shipping AI into real workflows and enabling them to own the systems long-term.
You'll drive build-vs-buy decisions, run rapid POCs with the judgment to commit hard and kill fast, and work directly with executive leadership. Your work will inform how the company makes decisions daily. The role reports to the VP of Customer Experience Innovation and requires comfort with founding-engineer ownership, consulting-style embedded work, and the ability to balance shipping velocity with trustworthiness standards.
Jobber is a B2B SaaS platform helping service businesses (lawn care, plumbing, cleaning, painting, etc.) connect with customers, manage operations, invoice, 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 demonstrated how confidently AI can fail
- Pragmatic technology instincts: default to proven tools and can defend exceptions
- Founding-engineer, consulting, or forward-deployed experience: comfortable owning outcomes in unfamiliar domains
- Daily working relationship with AI tools and agents as instruments you build with and build for
- Ability to ship every few weeks while maintaining trustworthiness standards and communicate both to executive leadership
