Principal Engineer (AI, Office of the CEO)

About the role

The Principal Software Engineer will serve as the founding technical lead within the Office of the CEO, tasked with architecting and building internal AI systems to transform company operations. This role involves working across the modern AI stack to deliver production-ready solutions while collaborating directly with executive leadership. The position requires a builder's mindset to design, implement, and scale AI systems that improve trust, security, and workflow efficiency across the organization.

Responsibilities

• Architect and build new internal AI systems end to end, from first design to production.
• Own the hard parts of trustworthy AI at company scale, including retrieval quality, permissions, security, and reliability.
• Work hands-on across the modern AI stack, such as LLMs, retrieval, agents, and integrations.
• Embed with teams across the company to ship AI into real workflows and establish sustainable systems.
• Drive build-vs-buy evaluations and execute fast proof-of-concept projects.
• Work directly with executive leadership to inform company decision-making through technical implementation.

Required skills

• AI systems
• Data infrastructure
• Retrieval
• LLMs
• Agents
• System architecture

Qualifications

• Track record of building production systems at Staff+ scope
• Hands-on experience with modern AI stacks
• Founding-engineer, consulting, or forward-deployed experience

Benefits

• Equity rewards
• Health insurance
• Retirement savings matching
• Annual wellness stipend
• Career coaching
• Talent development program

About the Company

Jobber is a technology company transforming the service industry by helping small businesses like lawn care providers, plumbers, and cleaners connect with customers, save time, and get paid. The company supports tens of thousands of users in delivering billions of dollars in services annually.