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Added 23 mins ago
NG
Red Seal Electrician
New Gold Inc.
Kamloops, BC
- Full-time
Install, troubleshoot, design, commission, and maintain all control systems, electrical, hydraulic, motor control, VFDs, radios, and solid-state controllers associated with the surface and…
Added 23 mins ago
A
Senior Mechanical Design Engineer
Actalent
Cambridge, ON
- $45 to $65 CAD / hour
- Contract
Communicate requested design changes to the Project Lead or Team Lead and ensure they are accurately implemented.
Added 23 mins ago
CG
Regional Account Manager (Coffee & Vending Services)
Compass Group Canada
Calgary, AB
- Full-time
A good business acumen that enables you to quickly understand and deal with situations that lead to a favourable outcome
Added 23 mins ago
BV
Customer Experience Lead
Betstamp Ventures
Toronto, ON
- Full-time
Small by design. One team runs all four businesses, so there's a lot of ground per person, and you're trusted with real scope early.
Added 38 mins ago
M
Senior Games Strategy Manager - Casino
Midnite
Remote, Canada
- Full-time
- Remote
We’re looking for a Senior Games Strategy Manager, to lead the launch, growth, and long-term performance of Midnite’s casino operations within the Canadian market.
Added 38 mins ago
MM
Oliver Wyman - Senior Lead AI Developer
Marsh McLennan
Toronto, ON · Montreal, QC
- Full-time
…unique and unprecedented products across industries. As a Senior Lead AI Developer, you are primarily responsible for managing technical projects and helping teams design and build AI/ML…
Added 53 mins ago
SQ
Bilingual ADP Sales Manager
Sunlife Québec
Quebec, QC
- Full-time
In this role, you will lead, coach and develop a team of advisors, helping them build confidence, strengthen sales capabilities and deliver meaningful outcomes for clients. Through…
Added 53 mins ago
AH
Registered Nurse
Alberta Health Services
AB · Greater Edmonton Metropolitan Area
- Full-time
As a key member of our interprofessional team on Unit 4C, you will lead integrated, intensive rehabilitation for medically complex older adults. You will design and execute nursing care…
Added 1 hour ago
IE
Analyst, Business
IMAX Enhanced | Streaming & Consumer Technology
Mississauga, ON
- Full-time
…requirements, improve business processes, support solution design and delivery, and help ensure technology investments generate measurable business…
Added 1 hour ago
N
Enterprise Marketing Campaign Manager - Montreal
Naboo
Montreal, QC
- Full-time
You design segmented, multi-channel campaigns, not just run them, and you judge them on pipeline, not opens.
Added 1 hour ago
E
Lead Mechanical Engineer
Englobe
Saskatoon, SK
- Full-time
As a Lead Mechanical Engineer, you will work in collaboration with the Mechanical Design Team in our Englobe Saskatoon office.
Added 2 hours ago
S
Communication & Social Media Specialist - VIE Contract
Sanofi
Toronto, ON
- Full-time
Own and lead the editorial and social media strategy across internal and external owned channels.
Added 2 hours ago
BA
Senior Tunnel Engineer
Brierley Associates Corporation
NB · Chiasson Office, NB
- Full-time
Brierley Associates seeks qualified candidates to join and support our Tunnel Design group. The successful candidate will lead and contribute to soft ground, rock, and mixed-face tunnel…
Added 2 hours ago
C-
Technical Sales and Field Service Engineer
Captiveaire - Region 114 Western PA
Ottawa, ON
- Full-time
Leader in the industry for over 40 years with innovative technologies, unmatched service, competitive pricing, and rapid lead times.
Added 3 hours ago
J
Senior Software Developer (C#/.NET and React)
Jobgether
Canada
- Up to $120,000 CAD / year
- Full-time
Lead feature-level technical design decisions, including API architecture, data models, and system integrations.
Added 3 hours ago
A
Forward Deployed AI Engineer - Senior Manager
Accenture
Calgary, AB · Vancouver, BC · Ottawa, ON · Toronto, ON
- Full-time
Lead executive workshops, board-level engagements, architecture design sessions, code-with sessions with client engineering and C-suite leadership teams, and cross-practice architecture…
Added 3 hours ago
S
Utilities Manager - ALTO
SYSTRA
Montreal, QC
- Full-time
SYSTRA Canada is part of the SYSTRA group, an international consulting and engineering group, a world leader in the design of transport infrastructures. SYSTRA Canada is an engineering and…
Added 3 hours ago
S
External Interface Engineer - ALTO
SYSTRA
Montreal, QC
- Full-time
SYSTRA Canada is part of the SYSTRA group, an international consulting and engineering group, a world leader in the design of transport infrastructures. SYSTRA Canada is an engineering and…
Added 3 hours ago
H
VMware Infrastructure Specialist
HCLTech
AB · Edmonton, AB
- $89,000 to $117,000 CAD / year
- Full-time
Lead VMware architecture, design, and implementation activities.
Added 3 hours ago
UO
Director, Office of Education
University of Alberta
Edmonton, AB
- Full-time
The College of Natural and Applied Sciences (CNAS) is hiring a Director, Office of Education to lead the academic administration services in the Office of Education. Reporting to the…
Added 4 hours ago
AA
Professionnel en Systèmes Électriques - Gestion des requis et V&V / Electrical Systems Professional - Requirement management and V&V
Airbus Aircraft
Montreal, QC
- Full-time
Added 4 hours ago
AA
Intégrateur système nacelle / Nacelle System Integrator
Airbus Aircraft
Montreal, QC
- Full-time
Added 4 hours ago
AA
Professionnel en ingénierie de liaison MAP / Liaison Engineering MAP
Airbus Aircraft
Montreal, QC
- Full-time
Do you have experience in aircraft design or repairs, have you worked in engineering and would you like to progress and develop new skills? Then this job is for you!
Added 4 hours ago
O
National Accounts Director
OPENLANE
Brampton, ON
- $100,000 to $125,000 CAD / year
- Full-time
Executive Reporting Design: Mastery in translating complex operational performance metrics into concise, professional review decks for corporate clients and internal leaders.
Added 4 hours ago
AA
Spécialiste Risque Électromagnétique / Electromagnetic Hazard Specialist
Airbus Aircraft
Montreal, QC
- Full-time
Supporter les DADs (Design Authority Delegates) dans la revue et approbation de documents pour la certification.

FutureSight

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

Canada

Full-time

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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 and go-to-market development. Partner with FutureSight to build and iterate on the product, raise seed capital, and recruit and lead the founding team.

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 retain talent. Direct experience in commercial P&C insurance distribution - such as agency, brokerage, MGA, or insurtech work - is sought, ideally with carrier relationships or a producer license.

Skills

Venture Founding
B2B SaaS Go-to-Market
Sales
Customer Development
Fundraising
Investor Relations
Insurance Brokerage
Carrier Relationships
Product Strategy
Pricing Strategy
Market Positioning
Team Building
Talent Development
Leadership
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
Carrier Relationships
Producer License
B2B SaaS
Go-to-Market
Customer Development
Ideal Customer Profile
Pricing Model
Product Positioning
Customer Pilots
Policy Binding
Certificates of Insurance
Multi-Carrier Quoting
AI Agents
Product Development
Seed Fundraising
Venture Building
Team Building
Market Research
Insurance Renewals

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