Description
We're looking for a Principal Software Engineer, AI, to join the Office of the CEO at Jobber. As the founding technical lead, you'll architect and build new AI systems from scratch, focusing on trust, permissions, security, and quality at scale.
The Team: You'll work in a small, senior team within the Office of the CEO, tasked with reinventing how a 1,000-person company operates in the AI era. You'll have direct access to decision-makers and will ship real products frequently.
The Role: As the Principal Software Engineer, AI, you'll:
- Design and build new internal AI systems end-to-end, from concept to production
- Tackle the challenging aspects of trustworthy AI at company scale, including retrieval quality, permissions, security, and reliability
- Work hands-on with the modern AI stack, balancing pragmatism with innovation
- Collaborate with teams across the company, embedding with function leaders and their teams, and working with executive leadership
- Drive build-vs-buy decisions and rapid POCs, with the judgment to commit or cancel quickly
- Work closely with executive leadership, informing company decisions daily
Requirements:
- Proven track record of building production systems at a high level (Staff+ scope) in data infrastructure, retrieval, or applied AI
- Hands-on experience with the modern AI stack and a battle-tested understanding of AI's capabilities and limitations
- Pragmatic technology instincts, favoring proven tools and defending exceptions
- Experience as a founding engineer, consultant, or forward-deployed expert, comfortable owning outcomes in unfamiliar domains
- Daily working relationship with AI tools and agents, as instruments for building and delivering solutions
- Ability to ship trustworthy solutions every few weeks, with strong communication skills to explain complex concepts to non-technical stakeholders
What You Can Expect:
- Comprehensive compensation package, including extended health benefits, RRSP/TFSA/FHSA matching, and stock options
- Dedicated Talent Development team and access to coaching, learning, and leadership programs
- Opportunity to impact a $400 billion industry with no dominant player
- Collaborative, humble, and supportive work environment
About Jobber: Jobber transforms how service is delivered, connecting small businesses with customers and enabling them to save time, invoice faster, and get paid.