Principal Engineer (AI, Office of the CEO)
Jobber · Remote · Boston ·
COMPENSATION
€•• – ••k
Listed on the employer's job board (Ashby)
- Principal / Staff+ level
- Fully remote
- AI & LLM focus
- Founding engineer role
- High impact on strategy
Join a small, senior team within the Office of the CEO tasked with reinventing how Jobber operates in the AI era. As the founding technical seat, you will build new AI systems from zero to production, addressing complex challenges like trust, security, and scale. You will work directly with executive leadership and function leaders to ship practical AI solutions that become core to the company's operations.
What you'll do
- Architect and build internal AI systems end-to-end as the founding engineer
- Solve hard problems regarding retrieval quality, permissions, and security at scale
- Work hands-on with LLMs, agents, and integrations using pragmatic technology choices
- Embed with cross-functional teams to ship AI into real daily workflows
- Drive build-vs-buy evaluations and run fast proofs of concept
- Collaborate weekly with executive leadership to inform decision-making processes
What you'll need
- Track record of building production data or AI systems at Staff+ scope
- Deep hands-on experience with the modern AI stack and retrieval systems
- Experience dealing with the limitations and errors of confident AI models
- Pragmatic approach to technology selection, favoring proven tools
- Background in founding-engineer, consulting, or forward-deployed roles
- Daily proficiency with AI tools and agents for building and productivity
- Ability to ship frequently while maintaining high standards of trustworthiness
Stack
- LLMs
- Retrieval systems
- AI Agents
- Integrations
How you'll work
- Fully remote position
- Reports to VP of Customer Experience Innovation
- Small senior team in Office of the CEO
What you get
- Competitive salary range with equity rewards
- Extended health benefits with fully paid premiums
- Retirement savings matching (RRSP, TFSA, FHSA)
- Annual stipends for health and wellness
- Access to talent development programs and career coaching
- Inclusive and supportive work environment