Principal Engineer (AI, Office of the CEO)
Jobber · Remote · Remote ·
COMPENSATION
€•• – ••k
Listed on the employer's job board (Ashby)
- Principal / Staff+ level
- Fully remote
- AI & LLM focus
- Founding engineer role
- Equity included
Join a small, senior team inside Jobber’s Office of the CEO with a mandate to reinvent how the company operates in the AI era. As the founding technical seat, you will build new AI systems from zero to production, solving hard problems around trust, security, and scale.
You will work directly with executive leadership and embed with various teams to ship working AI into real workflows. The role requires pragmatic technology choices, fast iteration, and the ability to set technical standards for AI across the organization.
What you'll do
- Architect and build internal AI systems end-to-end as the founding engineer
- Own retrieval quality, permissions, security, and reliability at scale
- Work hands-on with LLMs, retrieval, agents, and integrations
- Embed with teams to ship AI into real workflows and establish owners
- Drive build-vs-buy evaluations and execute fast proofs of concept
- Collaborate directly with executive leadership on strategic decisions
What you'll need
- Track record building production data or AI systems at Staff+ scope
- Deep hands-on experience with the modern AI stack and LLMs
- Pragmatic technology instincts favoring proven tools
- Experience in founding-engineer, consulting, or forward-deployed roles
- Daily working relationship with AI tools and agents
- Ability to ship frequently while maintaining high trust standards
Stack
- LLMs
- Retrieval systems
- AI agents
- Data infrastructure
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
- Annual salary range $196,300 to $265,600 USD
- Equity rewards and stock options
- Extended health package with fully paid premiums
- Retirement savings matching (RRSP, TFSA, FHSA)
- Annual stipends for health and wellness
- Access to talent development and career coaching