Founding AI Systems Engineer – Trustworthy at Scale

Jobber; Massachusetts; On-site; USD 229,000 - 310,000; Full time

Benefits offered by this job

Stock options

Extended health benefits

Retirement matching

Talent Development program

Job summary

Jobber is looking for a Principal Software Engineer, AI, to join the Office of the CEO and lead the creation of production AI systems at scale. You will architect, build, and own the hard problems around trust, security, and reliability while shipping AI into real workflows across the company.

This is a founder-style role requiring hands-on delivery, fast decision-making, and close collaboration with executive leadership to shape how the company runs with AI.

Qualifications

• Experience building production AI or data systems used by hundreds to thousands of people.
• Hands-on depth with the modern AI stack and experience with at least one system showing AI could be wrong.
• Founding-engineer, consulting, or forward-deployed experience with ownership responsibilities.

Responsibilities

• Architect and build new internal AI systems end to end, from 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 foundations pragmatic.
• Embed with teams across the company and with executive leadership, shipping AI into real workflows and leaving behind enduring systems.
• Drive build-vs-buy evaluations and fast POCs, with the judgment to commit or kill fast.
• Share with executive leadership how your work informs company decisions every day.

Skills

Staff+ experience

Production AI

Data infrastructure

Retrieval systems

AI safety

Architectural design

Hands-on AI

Tools

LLMs

Retrieval framework

Security tooling

Job description

Jobber is looking for a Principal Software Engineer, AI, to join the Office of the CEO and lead the creation of production AI systems at scale. You will architect, build, and own the hard problems around trust, security, and reliability while shipping AI into real workflows across the company.

This is a founder-style role requiring hands-on delivery, fast decision-making, and close collaboration with executive leadership to shape how the company runs with AI.