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Principal Engineer (AI, Office of the CEO)

jobberBostonProduct Engineering
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Salary
Not listed
Job type
Full-time
Work mode
Remote
Experience
Senior
Posted
25 Sept 2026
Status
Open · checked 7d ago

About this role

Based in Boston, the Principal Software Engineer position at Jobber places a technical leader inside the Office of the CEO to build core internal artificial intelligence systems. This role suits an experienced engineer with a background in shipping production-grade data and AI infrastructure at a high level.

Role Overview

Operating within a dedicated startup unit inside Jobber, this founding technical role focuses on redesigning internal company operations through artificial intelligence. The position reports to the VP of Customer Experience Innovation and collaborates directly with executive leadership and functional teams to deploy production systems that handle trust, security, permissions, and scalability.

Key Responsibilities

Architect and build new internal artificial intelligence systems from initial design to production deployment as the founding engineer.
Manage complex operational requirements including retrieval quality, system reliability, security, and access permissions.
Work hands-on across modern artificial intelligence technologies such as large language models, retrieval mechanisms, agents, and integrations.
Embed directly with departmental leaders and teams to integrate solutions into daily workflows.
Conduct build versus buy evaluations, execute rapid proofs of concept, and determine technology directions.
Coordinate closely with executive leadership to inform organizational decision-making through technical development.

Requirements

Demonstrated track record of constructing production systems at a Staff level or higher, including data infrastructure, retrieval systems, or applied artificial intelligence used by hundreds or thousands of individuals.
Hands-on familiarity with the modern artificial intelligence stack and direct experience managing failure modes in complex systems.
Pragmatic technical instincts focused on proven tooling and defensible architectural choices.
Prior founding engineer, consulting, or forward-deployed operational experience.
Daily working familiarity with artificial intelligence tools and agents.
Ability to ship frequently while maintaining trustworthiness and communicating clearly with executive leadership.

Skills and Tools

Large Language Models (LLMs)
Retrieval systems
AI agents
Software integrations
Production data infrastructure

Salary and Benefits

Annual salary range with a minimum of $229,300, a midpoint of $269,700, and a maximum of $310,200.
Equity rewards and stock options.
Extended health benefits package with fully paid premiums.
Retirement savings matching options including RRSP, TFSA, or FHSA.
Annual stipends for health and wellness.
Access to a dedicated talent development program featuring career coaching and leadership training.

About the Company

Jobber develops technology that helps home service providers such as lawn care operators, house cleaners, plumbers, and painters manage their operations, connect with customers, streamline invoicing, and receive payments. The company aims to support small business success across a multi-billion dollar service industry.

How to Apply

Candidates should apply on the official company careers page.

Skills and tech stack

LLMsRetrieval systemsAI agentsIntegrations

Questions candidates ask

Where is the Principal Software Engineer position located?

The role is based in Boston.

Who does this role report to?

The position reports to the VP of Customer Experience Innovation.

What is the salary range for this role?

The salary ranges from a minimum of $229,300 to a maximum of $310,200, with a midpoint of $269,700.

What team does this position join?

The role joins a specialized team inside the Office of the CEO.

Ready to apply?

The application is on the official jobber careers page.

Apply on company site