Founding AI Engineer—Internal Systems Leader

RiseMe; Boston (MA); On-site; USD 229,000 - 310,000; Full time

Benefits offered by this job

Extended health benefits

Stock options

Talent development programs

Transparent compensation discussion

Job summary

Jobber is seeking a Principal Software Engineer, AI, to join the Office of the CEO and lead the architecture and delivery of AI systems at scale. You will own core AI platforms, drive trustworthy AI practices, and collaborate with executives to align technical outcomes with business goals.

This role requires hands-on work across the AI stack, fast iteration, and the ability to ship AI into real workflows while setting durable technical standards for the organization.

Qualifications

• 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 showed you how confidently AI can be wrong.
• Pragmatic technology instincts: you reach for proven tools by default and can defend the exceptions.
• Founding-engineer, consulting, or forward-deployed experience: comfortable owning outcomes inside someone else's domain.
• A daily working relationship with AI tools and agents, as instruments you build with and build for.
• The pragmatism to ship every few weeks, the standards to make it trustworthy anyway, and the communication skills to explain both to a CEO.

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.

Job description

Jobber is seeking a Principal Software Engineer, AI, to join the Office of the CEO and lead the architecture and delivery of AI systems at scale. You will own core AI platforms, drive trustworthy AI practices, and collaborate with executives to align technical outcomes with business goals.

This role requires hands-on work across the AI stack, fast iteration, and the ability to ship AI into real workflows while setting durable technical standards for the organization.