Co-Founder & CEO, AI-Native Insurance Brokerage

Toronto, Ontario

On-site

Full-time

No salary posted2 days ago

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Employment type: Full-time · On-site
Posted: November 4, 2026
Province: Ontario (ON)

Hiring confidence: Sparse posting · 22/100

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Job Overview

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Job Description Job Description The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Keystead, an AI-native insurance brokerage venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Keystead is an insurance brokerage built for the small businesses traditional brokers can't afford to serve. AI agents run the full workflow, from intake and multi-carrier quoting to binding and certificates of insurance, with licensed agents stepping i…

This role is based in Ontario. FutureSight Ventures is hiring for this full-time position through Jobily, where you can check how well your resume matches the posting before you apply.

Market context

About this role in Ontario

Average salary for Co-Founder & CEO, AI-Native Insurance Brokerage in Ontario

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Typical qualifications for Canadian employers

Founder mentality and equity partnership commitment
Deep knowledge of insurance industry or related sectors
Experience building and scaling technology-driven businesses
Understanding of AI/automation in enterprise workflows
Ability to work with minimal constraints and ambiguity

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What you'll do

Lead overall strategy and vision for Keystead
Build and scale founding team
Drive product development of AI-native insurance platform
Oversee operations from intake through certificate issuance
Manage relationships with insurance carriers
Lead fundraising efforts
Ensure regulatory compliance and licensing requirements
Drive customer acquisition and business growth
Coordinate between AI systems and licensed agents
Build small business market positioning

What you'll need

Founder mentality and equity partnership commitment
Deep knowledge of insurance industry or related sectors
Experience building and scaling technology-driven businesses
Understanding of AI/automation in enterprise workflows
Ability to work with minimal constraints and ambiguity
Strong network in insurance, small business, or fintech
Track record of raising capital or building ventures