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Added 4 mins ago
RG
Senior Finance Business Partner
RWS Group
Montreal, QC
- Full-time
The Senior Finance Business Partner (FBP) will be responsible for providing financial support to the divisional management team and for driving the financial performance of the business,…
Added 34 mins ago
CB
Technical Sales Representative - Professional Turf
Certis Belchim
Canada
- Full-time
…will have the autonomy to develop and execute your territory strategy, build strong relationships with retailers and turf professionals, and help shape the growth of our Professional Turf…
Added 1 hour ago
HM
Family Practitioner/General Practitioner
Health Match BC
Lillooet, BC
- Full-time
The first of its kind in Canada, FNHA works as a health-and-wellness partner with BC First Nations to support self-determination and decision-making to improve health outcomes.
Added 2 hours ago
HM
Family Practitioner/General Practitioner
Health Match BC
Williams Lake, BC
- Full-time
The first of its kind in Canada, FNHA works as a health-and-wellness partner with BC First Nations to support self-determination and decision-making to improve health outcomes.
Added 2 hours ago
MC
Product Marketing Manager - Trading
Moomoo Canada
Toronto, ON
- Full-time
Business Collaboration & Optimization: Partner with Business Development (BD) to ensure content strategies drive user acquisition; monitor performance metrics, iterate content based on…
Added 2 hours ago
M
Product Marketing Manager - Trading
moomoo
Toronto, ON
- Full-time
Business Collaboration & Optimization: Partner with Business Development (BD) to ensure content strategies drive user acquisition; monitor performance metrics, iterate content based on…
Added 3 hours ago
A
Senior Manager, Strategic Partnerships – Japan Partnerships (Tokyo-based)
Agoda
Toronto, ON
- Full-time
Define and drive Agoda’s FI partnership strategy for Japan, aligned with market priorities and business growth objectives
Added 3 hours ago
A
Senior Manager, Strategic Partnerships – Japan Partnerships (Tokyo-based)
Agoda
Vancouver, BC
- Full-time
Define and drive Agoda’s FI partnership strategy for Japan, aligned with market priorities and business growth objectives
Added 3 hours ago
J
Founder, Data Centre Buildout
Jobgether
Canada
- Full-time
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Founder, Data Centre Buildout based in Canada.
Added 3 hours ago
ZG
Content Creator, Social & Digital
Zeno Group Canada
Toronto, ON
- Full-time
…of the Unexpected," we push the boundaries to achieve real business value and societal impact for clients. Winner of the industry’s most coveted awards including the 2024 PRWeek U.S.…
Added 3 hours ago
C
Director, Chapter Lead, Sales & Advice Capability Development
CIBC
Toronto, ON
- Full-time
Capability strategy and design - Set the framework and design principles for in-role sales and advice capability development across Banking Centre roles and leaders, ensuring solutions are…
Added 4 hours ago
HT
Director, Finance (CSM)
Husky Technologies
Bolton, ON
- Full-time
The Finance Director serves as a strategic business partner to the Leadership Team in support of Husky’s Global Service Business and Customer Success Management strategy. This role provides…
Added 4 hours ago
HT
Financial Manager - PLM (Product Line Mgmt)
Husky Technologies
Bolton, ON
- Full-time
We are looking for a high-impact Finance Manager FP&A to act as a true business partner to our Product Line leadership team.
Added 4 hours ago
R-
Director, Strategic Insights
RCL - Reitmans Canada Ltd/Ltée
Montreal, QC
- Full-time
…and behavioural data into actionable insights that support business decisions. Reporting to the VP, Data Strategy, this role partners with brands and cross-functional teams to strengthen…
Added 5 hours ago
FI
销售总监
Forestown International Consulting Inc.
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Develop and execute a 3-year business strategy and annual plan.
Added 5 hours ago
SAP Ariba / AP Solution Architect
Capgemini
Vancouver, BC
…expertise in Ariba Sourcing, Contracts, Buying & Invoicing, SAP Business Network, invoice automation, and SAP S/4HANA integration. Strong stakeholder management, workshop facilitation,…
Added 5 hours ago
J
Partner Development Manager, Ecosystem Partnerships
Jobgether
Canada
- Full-time
We are seeking an experienced Partner Development Manager to grow and manage a diverse portfolio of ecosystem partnerships. In this role, you will build scalable partner engagement…
Added 7 hours ago
FP
Manager Campaign Analytics SQL Pega CDH
FINTECH PROFESSIONALS CORP
Toronto, ON
- $50 to $65 CAD / hour
- Full-time
Partner with Campaign Design and Execution, Data Science, Marketing, Product, and channel teams to improve decisioning, personalization, next-best-action strategies, and multi-channel…
Added 7 hours ago
C
Sales Director
Convergint
Toronto, ON · CA ON Etobicoke
- Full-time
Develop a business plan and regional strategy to achieve sales and profitability goals.
Added 8 hours ago
U
Sr. Community Developer - Far Cry
Ubisoft
Montreal, QC
- Full-time
…deployment and maintenance of best practices. As a key strategic partner, they will prioritize global business growth opportunities by collaborating with transversal stakeholders as they…
Added 8 hours ago
R(
Director, Strategic Insights
Reitmans (Canada) Ltée/Ltd
Montreal, QC
- Full-time
…and behavioural data into actionable insights that support business decisions. Reporting to the VP, Data Strategy, this role partners with brands and cross-functional teams to strengthen…
Added 8 hours ago
C
Product Manager
Cvent
Fredericton, NB · Virtual, UNAVAILABLE
- Full-time
…destinations to help them grow their group/MICE and corporate travel business. Our technology brings millions of people together at events around the world. In short, we’re transforming the…
Added 8 hours ago
E
Brand, Marketing and Communications (BMC) - Specialist - Service Lines (3 months contract)
EY
Toronto, ON
- Contract
Translate business and stakeholder goals into effective marketing activities that connect brand to demand
Added 8 hours ago
Human Resources Business Partner
Toronto Community Housing or Toronto Seniors Housing
Toronto, ON
…aligns with TSHC's strategic priorities. The People and Culture Business Partner will also provide advice and guidance in all areas of people and culture administration to assigned client…
Added 9 hours ago
RP
Vice President Finance
RECRUITMENT PARTNERS INC.
AB · Edmonton, AB
- Full-time
…compliance while providing timely financial insight that supports business strategy, sustainable growth, and informed decision-making. The successful candidate will lead a global finance…

FutureSight

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

Canada

Full-time

Apply About employer

Applications open in a new tab.

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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