Co-Founder & CEO - AI Benefits & InsureTech

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

Job summary

An innovative tech venture in Canada is seeking a Founding CEO to lead their AI data infrastructure initiative for the employee benefits sector. This role involves winning customers, building the product, and raising capital while establishing a strong team culture. Ideal candidates should have previous founding experience, proven B2B SaaS sales success, and expertise in fundraising. A full-time commitment to building a new SaaS venture with significant equity stake is required.

Benefits

Significant equity stake

Pre-seed funding for early hires

Qualifications

• Previous founding experience in a product company or B2B SaaS venture.
• Ability to craft investor narratives and close capital.
• Magnet for top talent; capable of building an inclusive culture.

Responsibilities

• Win customers by validating retention and running pilots.
• Build the product in collaboration with the engineering team.
• Lead the seed round and manage initial fundraising efforts.
• Hire the founding team and establish company culture.

Skills

B2B SaaS sales

Fundraising

People leadership

Risk appetite

Startup scrappiness

Customer engagement

Industry experience in employee benefits

Job description

FutureSight is seeking an experienced and visionary Founding CEO to lead the launch of a new AI data infrastructure venture serving the $20B+ employee benefits ecosystem across brokers, MGAs, and mid-market employers.

Today, brokers and HR teams struggle to make data-driven decisions because benefits data is often locked in carrier portals, PDFs, and spreadsheets, leading to opaque renewals, manual reporting, and poor cost control.

Our venture is building an AI-powered data platform that automatically extracts and standardizes benefits data from carriers and brokers, producing instant renewal models, benchmarking insights, and compliance-ready dashboards. The result: faster renewals, clearer cost transparency, and smarter plan design.

As Founding CEO, you will

• Win customers — Run pilots, shape pricing, and validate retention + 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.

About FutureSight

FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage — pairing hands‑on studio support with early capital, thereby reducing risk and increasing the odds of success by 10x.

We’re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise, Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi‑time exited founder, and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.

What We Bring

• Validated problem — You will enter a venture with a proven market need and strong momentum toward building and scaling.
• Studio bench strength — Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1.
• Capital commitment — Initial pre‑seed funding for early hires and building the MVP with potential for follow‑on funding, and access to our investor and advisor network.

What You Bring

• Founder-level drive — You’re motivated to co-found a new venture as the CEO. With or without us, this is your calling.
• Startup scrappiness — You know what you’re signing up for. You’re familiar with the scrappiness of owning something from start to finish.
• Previous founding experience — You have co‑founded a product company or B2B SaaS venture or have been at a venture‑backed company.
• Risk appetite and capacity — Read more on our post on the Entrepreneurial Risk Profile.
• GTM chops — Proven success in B2B SaaS sales, marketing, and customer engagement.
• Fundraising fluency — Able to craft investor narratives and close capital; well‑networked 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.

What You Can Expect

• Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise.
• Full P/L ownership of the new entity.
• A significant equity stake in the business.
• This is a full‑time role; we are looking for someone to commit full‑time and exclusively to building and owning a new SaaS venture.

Ready to build?
If this is the perfect opportunity for you, we want to hear from you!

Submit your Resume and LinkedIn profile and tell us more about why you think we should chat!

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