Principal Engineer (AI, Office of the CEO)

About the role

The Principal Software Engineer, AI will serve as the founding technical lead within the Office of the CEO to architect and build internal AI systems. This role involves working across the modern AI stack to reinvent company operations and shipping production-ready AI solutions that impact every function at Jobber. The position requires a builder's mindset to design systems from scratch, evaluate build-vs-buy decisions, and ensure reliability and security at scale.

Responsibilities

• 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.

Required skills

• AI systems
• Data infrastructure
• LLMs
• Retrieval
• Agents
• Production systems

Qualifications

• Track record of building production systems at Staff+ scope
• Founding-engineer, consulting, or forward-deployed experience

Benefits

• Equity rewards
• Annual stipends for health and wellness
• Retirement savings matching
• Extended health package
• Career coaching
• Talent development program

About the Company

Jobber is transforming the way service is delivered by providing technology to small businesses like lawn care providers, cleaners, plumbers, and painters. The company helps these businesses connect with customers, save time, and manage invoicing to facilitate billions of dollars in services annually.