Opportunity at
JobberPrincipal Engineer (AI, Office of the CEO)
Jobber makes software that helps home service businesses, including lawn care companies, cleaners, plumbers and painters, connect with customers, bill faster and collect payments. It is…
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About This Role
Jobber makes software that helps home service businesses, including lawn care companies, cleaners, plumbers and painters, connect with customers, bill faster and collect payments. It is recruiting a Principal Software Engineer, AI, for its Office of the CEO. The unit is a small, senior group inside a company of about 1,000 people, charged with rethinking how the business operates in the AI era. The group ships new work often and…
Job Description
Jobber makes software that helps home service businesses, including lawn care companies, cleaners, plumbers and painters, connect with customers, bill faster and collect payments. It is recruiting a Principal Software Engineer, AI, for its Office of the CEO. The unit is a small, senior group inside a company of about 1,000 people, charged with rethinking how the business operates in the AI era. The group ships new work often and learns from each release.
This is a founding technical position. The engineer will architect new internal AI systems from initial design to production, owning the hard parts of retrieval accuracy, access control, security and uptime across the company. The work spans LLMs, retrieval, agents and integrations, with a bias toward practical foundations. The engineer will also work inside departments across the company, deliver AI into daily workflows, and leave behind systems that others can run. Other tasks include making quick build-or-buy decisions, running proofs of concept and stopping weak ones, and defining technical standards for AI across Jobber. Reporting line: the VP who leads Customer Experience Innovation. The role works closely with executive leadership.
Applicants should have built production systems at a staff-plus level, such as data platforms, search or applied AI that hundreds or thousands of people use each day. Deep hands-on experience with the modern AI stack, a record of sensible technology choices, and consulting or forward-deployed engineering experience are needed. The listed base salary is USD 229,300 to 310,200 per year, with a midpoint of 269,700. The total package includes equity, wellness stipends, retirement matching and extended health coverage.
Responsibilities
- Design and ship in-house AI systems end to end, serving as the founding engineer
- Own accuracy of retrieval, access rules, security and uptime for AI across the company
- Use the full AI stack, including LLMs, retrieval, agents and integrations, with pragmatic foundations
- Work inside teams across the company to bring AI into their processes and transfer ownership
- Lead build-or-buy assessments and quick proofs of concept
- Partner with executive leaders on decisions informed by AI systems
- Establish the technical standards that AI work across Jobber must meet
Requirements
- Production track record at staff-plus level across data platforms, search or applied AI
- Deep hands-on skill across the modern AI stack and lessons learned from a system that failed confidently
- Pragmatic instincts, preferring proven tools and justifying exceptions
- Consulting, founding-engineer or forward-deployed experience, working within another group's domain
- Daily use of AI tools and agents
- Able to explain technical trade-offs clearly to a CEO
Core Skills
Benefits
- Equity and yearly stipends for health and wellness
- Retirement matching, with RRSP, TFSA or FHSA options
- Extended health plan with premiums fully covered for physical and mental care
- Stock options
- Talent development program with coaching and leadership training
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Where is the job located?
The posting does not name a city or office. The listing marks the role as on-site.
What is the salary?
Pay runs from USD 229,300 at the low end to 310,200 at the top, with 269,700 as the midpoint, per year.
Who does the role report to?
Reporting line: the VP who leads Customer Experience Innovation.
What experience is needed?
Proven experience shipping production systems at staff-plus scope, plus hands-on work with the modern AI stack.
Sample Interview Questions
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