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Agency job

Chief Technology Officer, AI-Native Consumer Platform

Toronto, ON

Full time

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Public opening managed by Calliere Group. You can apply directly through RBB without creating an account, or view the original posting.

Recruitment agency:
Calliere Group
Location
Toronto, ON
Work model
Hybrid
Employment type
Full time
Experience level
Not publicly disclosed
Department
Not publicly disclosed
Function
Not publicly disclosed
Industry
Legal / Technology
Published
2026-10-07

Role description

CTO mandate for a profitable consumer legal-services business modernizing its client and case-management platform around AI. The role owns technology and product direction and is expected to remain hands-on while scaling the engineering organization.

Key responsibilities

  • Make the client portal and case-management environment AI-native across practice areas.
  • Own the product roadmap and prioritize requests from clients and internal legal/service teams.
  • Build a platform capable of absorbing acquisitions and supporting expansion into new consumer-law categories.
  • Hire and develop engineering, product, design and data capabilities.
  • Maintain direct technical involvement while setting architecture and delivery standards.

Qualifications

Profile

  • 5+ years as a startup CTO, founding CTO or senior engineering/product leader, with 0-to-1 ownership.
  • Demonstrated product judgment and practical AI implementation experience.
  • Ability to code and discuss technical trade-offs directly.
  • Hybrid availability in Toronto; Canadian work authorization required.

Additional information

Stack includes Node.js, TypeScript, React, Next.js, PostgreSQL, Python, FastAPI, PHP, Google Cloud and LLMs. Base compensation advertised at C$275,000–C$325,000+, plus a target bonus.

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Public opening managed by Calliere Group. RBB receives direct applications for sharing with the recruiter or agency responsible for the opening. Original posting