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Jobber is seeking a Principal Software Engineer, AI to join the Office of the CEO as a founding technical leader. This is a startup-within-a-company role with a mandate to reinvent how a 1,000-person organization operates in the AI era, with direct access to decision-makers and the backing to ship real impact.
You will be the founding technical seat, architecting and building new AI systems from zero to production. The role spans the full stack: designing novel AI architectures, owning the hard problems of trustworthy AI at scale (retrieval quality, permissions, security, reliability), and embedding with teams across Jobber to ship working AI into real workflows. You'll work hands-on with LLMs, retrieval systems, agents, and integrations while maintaining pragmatic technology choices.
Key responsibilities include:
- Architect and build internal AI systems end-to-end as the founding engineer
- Own trust, permissions, security, and reliability challenges for AI at company scale
- Work across the modern AI stack with deliberate pragmatism in tool selection
- Embed with cross-functional teams and executive leadership, shipping AI into real workflows
- Drive build-vs-buy decisions and rapid POCs with clear judgment on commitment and kill criteria
- Work directly with the CEO and executive team, informing daily company decision-making
Reporting to the VP of Customer Experience Innovation, you'll operate with unusual autonomy and range. One week you're designing a system nobody at Jobber has built; the next you're embedded with a function, shipping working AI and building sustainable ownership. You'll set technical standards for all AI work at the company.
Jobber is a B2B SaaS platform serving the $400-billion service industry, helping tens of thousands of small businesses (lawn care, plumbing, cleaning, painting, etc.) connect with customers, manage operations, invoice, and get paid. The company has ~1,000 employees and is backed by significant resources to execute this AI transformation.
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 significant battle scar from a system that demonstrated AI's failure modes
- 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 both instruments to build with and build for
- Ability to ship every few weeks while maintaining trustworthiness standards and communicating both to executive leadership
