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Senior Manager, Analytics and Insights
TD
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- Full-time
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FutureSight

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

Canada

Full-time

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Job details

Job type: Full-time
Posting language: English
Posted: Nov 3, 2026

Original 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 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.

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More about this job

Responsibilities

Set Keystead’s strategic direction, refine its target customer, pricing, and positioning, and lead customer pilots through policy binding. Partner with FutureSight to build and iterate on the product, raise seed capital, recruit the founding team, and establish the company culture.

Requirements

Candidates should have prior founding experience at a venture-backed company, a record of B2B SaaS go-to-market success, fundraising fluency, and the ability to attract and lead talent. Direct experience in commercial P&C insurance distribution is sought, ideally including carrier relationships or a producer license.

Skills

Venture Founding
B2B SaaS Go-to-Market
Sales
Customer Development
Fundraising
Investor Relations
Talent Recruitment and Leadership
Insurance Brokerage
Carrier Relationships
Product Strategy
Pricing Strategy
Go-to-Market Strategy
Pilot Management
AI Product Development

Benefits

Founder Equity
Pre-Seed Capital
Venture-Building Resources
Design, Engineering, Growth, and Fundraising Support
Investor and Advisor Network

Visa sponsorship

Not detected in the job text

Keywords

InsurTech
AI-Native Insurance Brokerage
Small Business Insurance
Commercial P&C Insurance
Insurance Distribution
Insurance Agency
Managing General Agent
Producer License
Carrier Relationships
Multi-Carrier Quoting
Policy Binding
Certificates of Insurance
Insurance Renewals
B2B SaaS
Go-to-Market Strategy
Customer Development
Ideal Customer Profile
Pricing Model
Product Positioning
Pilot Programs
Seed Fundraising
Pre-Seed Capital
Venture Building
AI Agents
Product Development
Founding Team
Investor Relations

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