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

Canada
Remote
Posted Oct 5, 2026
1 position

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Employment type: Full-time
Experience level: Lead · 10+ years
Posting language: English
Working hours: 40 hours per week
Location requirements: Country, Toronto, Ontario, Canada
Seniority: Executive

Job summary

Set Keystead’s strategic direction and lead customer development, including pilots with small businesses, converting customers to bound policies, and building the go-to-market motion. Partner with FutureSight to ship and improve the product, lead the seed raise, and recruit and lead the founding team.

Job details

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. Keystead starts with the businesses that need proof of coverage again and again, such as contractors, event vendors, and product brands selling into retail. For these owners, a certificate that takes days to arrive can cost them the job. Keystead issues it in minutes, explains coverage in plain language, and re-shops the market at every renewal. Market Context Roughly 35M small businesses in the US are underserved by a broker model built for larger accounts. Across the US and Canada, small business insurance represents a $6.2B commission pool. About $4.5B of that comes from businesses that already carry commercial insurance. Digital buying is proven, with the leading digital insurer serving more than 750K small businesses. The multi-carrier, servicing-first model remains open. About FutureSight FutureSight is a leading venture builder that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale. You’ll co-create with a proven venture building team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. The Partnership Founder equity with meaningful ownership from inception Pre-seed capital committed by FutureSight for early hires and MVP development, with potential for follow-on funding Venture building resources, including embedded design, engineering, growth, and fundraising support from day one Investor and advisor network across insurtech and early-stage capital markets A true co-creation model in which you operate as CEO with FutureSight’s cross-functional team as your partner What You’ll Own As Co-Founder & CEO, you will set the venture's direction and lead execution. Strategy — Refine the ICP, pricing model, and product positioning Customer Development — Lead pilots with small business owners in certificate-heavy verticals, convert them to bound policies, and build the go-to-market motion Product — Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback Capital — Lead the seed raise, supported by FutureSight's network and traction Team — Recruit and lead the founding team, and establish the cultural foundation of the company Co-Founder Profile Previous founding experience at a venture-backed company Demonstrated success in B2B SaaS go-to-market, including sales and customer engagement Fundraising fluency, with the ability to develop investor narratives and close capital Proven ability to attract, develop, and retain top talent Clear-eyed understanding of the risks and demands of co-founding a venture-backed company Direct exposure to commercial P&C insurance distribution, such as agency, brokerage, MGA, or insurtech experience, ideally with carrier relationships or a producer license How To Apply Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate. FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.

What you’ll do

Requirements

Candidates should have prior venture-backed founding experience, demonstrated B2B SaaS go-to-market success, fundraising fluency, and a record of attracting and retaining talent. Direct experience in commercial P&C insurance distribution—ideally including carrier relationships or a producer license—is also sought.