Co-Founder & CEO — InsurTech | AI-Native Insurance Brokerage

Queen's Park, City of Toronto

On-site

Full-time

No salary postedYesterday

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Employment type: Full-time · On-site
Posted: November 3, 2026
Province: Ontario (ON)

Hiring confidence: Sparse posting · 22/100

This posting is missing most of the signals we look for, or shows patterns common to listings that are not actively being filled. Check with the employer before applying. How this is scored

Job Overview

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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 in where judgment matters. Keyst…

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 — InsurTech | AI-Native Insurance Brokerage in Ontario

We do not have a salary benchmark for this title in Ontario yet. The posting does not state a salary either.

NOC code

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Typical qualifications for Canadian employers

Co-founder partnership with meaningful founder equity
Leadership experience building and scaling companies
Deep understanding of insurance industry or demonstrated ability to learn quickly
Experience with AI/automation technologies
Fundraising capability and investor relations experience

Fit check

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What you'll do

Lead overall vision and strategy for Keystead
Build and scale the founding team
Oversee AI agent workflow development and integration
Manage relationships with licensed insurance agents
Drive customer acquisition for small business segment
Secure funding and manage financial planning
Establish partnerships with insurance carriers
Ensure regulatory compliance in insurance operations

What you'll need

Co-founder partnership with meaningful founder equity
Leadership experience building and scaling companies
Deep understanding of insurance industry or demonstrated ability to learn quickly
Experience with AI/automation technologies
Fundraising capability and investor relations experience
Business acumen in B2B SaaS or marketplace models