Co-Founder & CEO - AI Benefits & InsureTech

FutureSight; Toronto; On-site; CAD 150,000 - 250,000; Full time

Benefits offered by this job

Significant equity stake

Full P/L ownership

Daily active engagement with the team

Job summary

An innovative tech startup in Toronto seeks a visionary Founding CEO to launch an AI-powered data infrastructure venture in the employee benefits ecosystem. This role involves building an AI platform, driving customer engagement, and leading fundraising efforts. Ideal candidates should have previous founding experience, strong B2B SaaS expertise, and a proven track record in stakeholder engagement. A commitment to diversity and inclusion is emphasized, along with a full-time dedication to the venture and a significant equity stake in the new business.

Qualifications

• Motivated to co-found a new venture as CEO.
• Comfortable owning a venture from start to finish.
• Co-founded a product company or B2B SaaS venture.
• Willingness to engage in entrepreneurial risk.
• Proven success in B2B SaaS sales, marketing, and customer engagement.
• Able to craft investor narratives and close capital.
• Attract top talent and maintain company culture.
• Background in employee benefits or insurtech/HR data products.

Responsibilities

• Run pilots, shape pricing, and validate customer retention.
• Work with the product/engineering team to launch V1.
• Lead the seed round with initial investment.
• Hire the founding team and establish the company culture.

Skills

Founder‑level drive

Startup scrappiness

B2B SaaS sales expertise

People leadership

Fundraising fluency

Industry experience in employee benefits

Job description

Overview

FutureSight seeks a visionary Founding CEO to launch an AI-powered data infrastructure venture for the $20B+ employee benefits ecosystem across brokers, MGAs, and mid‑market employers. The role involves building an AI platform that extracts and standardises benefits data, launches the first version, and drives growth and capital raising.

Responsibilities

• Win customers – Run pilots, shape pricing, and validate retention and expansion.
• Build the product – Work with FutureSight’s product/engineering pod to launch V1.
• Raise capital – Lead the seed round with our initial investment.
• Build your team – Hire your founding team and set the cultural foundation.

Qualifications

• Founder‑level drive – Motivated to co‑found a new venture as CEO.
• Startup scrappiness – Comfortable owning a venture from start to finish.
• Previous founding experience – Co‑founded a product company, B2B SaaS venture, or worked in a venture‑backed company.
• Risk appetite and capacity – Willingness to engage in entrepreneurial risk.
• GTM chops – Proven success in B2B SaaS sales, marketing, and customer engagement.
• Fundraising fluency – Able to craft investor narratives, close capital, and network in fintech and early‑stage communities.
• People leadership – Magnet for top talent; coach and culture carrier.
• Industry experience – Background in employee benefits, brokerage, or insurtech/HR data products.

Benefits & Expectations

• Daily active engagement with our team to launch the initial product, achieve first market traction, and prepare for seed fundraising.
• Full P/L ownership of the new entity.
• Significant equity stake in the business.
• Full‑time, exclusive commitment to building and owning a new SaaS venture.

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.