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Added 12 mins ago
CA
Graduate Assistant - Student Solutions Hub
Career and Professional Development Center
St. Mary's, NL · St Marys, NL
- Internship
Support student officers and the faculty advisor with formation of the proposed registered student organization (RSO), meeting logistics, peer-learning clinics, and officer transitions.
Added 12 mins ago
DB
Part Time Bridal Sales
David's Bridal
Woodbridge, ON
- $16 to $25.8 CAD / hour
- Part-time
…concerns with confidence. Know when to escalate and partner with leadership…
Added 12 mins ago
OS
Manager / Senior Manager, Healthcare - Industries and Government Practice
Optimus SBR
Toronto, ON
- Full-time
This role combines hands-on delivery, client leadership, and team development. As a Manager, you will be responsible for structuring complex problems, guiding teams, and working directly…
Added 12 mins ago
RC
Management Consulting Director, Technology
RSM Canada
Toronto, ON
- Full-time
This Director will combine strong business development capabilities with deep expertise in Technology Strategy, ERP Strategy, IT Architecture, and complex transformation program leadership.…
Added 12 mins ago
DB
Part Time Bridal Sales
David's Bridal
Dartmouth, NS
- $16 to $22.32 CAD / hour
- Part-time
…concerns with confidence. Know when to escalate and partner with leadership…
Added 13 mins ago
BT
Senior Manager, Small Business Services
Baker Tilly Canada
Winnipeg, MB
- Full-time
Team leadership. You will supervise, coach, and develop staff and remote team members on engagement files. This includes reviewing their work, giving regular performance feedback, and…
Added 13 mins ago
B
Business Development Manager
BMO
Vancouver, BC · WGA
- Full-time
Boldly Grow the Good in Business and Life - Become BMO's next Business Development Manager supporting BrokerEdge clients in making real financial progress. Situated in Vancouver BC this…
Added 27 mins ago
A
Senior Vice President, Energy
AECOM
Markham, ON · Thornhill, Ontario
- $300,000 to $350,000 CAD / year
- Full-time
AECOM is seeking a Senior Vice President, Energy to lead the growth, market positioning, and strategic development of our Energy business across Canada. Reporting as part of the broader…
Added 1 hour ago
B
Director, Office North America Workplace Services
BMO
Toronto, ON · YNG
- Full-time
Under the direct supervision of the Head, Global Workplace Services, this role is accountable for the strategic leadership, operational oversight and performance of the facilities related…
Added 1 hour ago
M
AVP Strategy - Intermediary, Product, Institutional
Manulife
Toronto, ON
- Full-time
…Institutional is a strategic partner to the relevant business leadership teams and a senior member of the GWAM Strategy team. The role drives the strategic plans for three executive…
Added 1 hour ago
Financial Advisor - Saskatoon CBC & Main Branch
Scotiabank
Saskatoon, SK
You can expect to be recognized and rewarded for high-performance. You’ll be supported by leadership through meaningful development conversations that enable faster advancement and internal…
Added 3 hours ago
M
AVP Retirement & Wealth Strategy
Manulife
Toronto, ON
- Full-time
…transformation of our global franchise. The role is trusted advisor to the entire Retirement & Wealth Leadership Team, providing key insights and information to drive the development and…
Added 3 hours ago
AC
Senior Accountant, Assurance and Accounting - Private Enterprise & Public Sector Audit
ACCA Careers
Vancouver, BC
- Full-time
…evolving business and financial reporting landscape. As a trusted advisor, you’ll provide comprehensive, tailored financial information that enables clients to make informed decisions with…
Added 3 hours ago
MG
HHR Coordinator Lead
Michael Garron Hospital
Toronto, ON
- Full-time
…all extern coordinators. The Lead drives strategic program development, oversees multi-specialty extern roles, leads quality improvement initiatives, data audits, and dashboards,…
Added 3 hours ago
HI
Senior Salesforce Developer
HRbrain Inc.
Toronto, ON
- Full-time
…practices, as well as DevOps/SRE to help bring to life the CRM Advisor Platform of the…
Added 3 hours ago
AI
Lead Consultant
Atlantis IT Group
Canada
- Contract
Provide subject matter expertise, help lead the technical teams and be a trusted advisor to the business.
Added 3 hours ago
EL
Concrete Restoration Specialist
Engineering Link
Toronto, ON
- Full-time
…required, summarizing the contractor's costs and being client advisor for award…
Added 3 hours ago
M
Manager, Consulting - Human Resources
MNP
Vancouver, BC
- Full-time
Make an impact with our Executive Search & Recruitment team as a Manager. As a trusted advisor, you will partner with clients to identify, attract and assess executive, senior leadership…
Added 4 hours ago
A&
Manager, Core Tax
Alvarez & Marsal
Toronto, ON
- Full-time
…design: we give people ownership and impact from day one, fuel development through real opportunity, and provide direct access to leaders who invest in our growth. Our culture celebrates…
Added 4 hours ago
A&
Associate, Restructuring
Alvarez & Marsal
Toronto, ON
- Full-time
…design: we give people ownership and impact from day one, fuel development through real opportunity, and provide direct access to leaders who invest in our growth. Our culture celebrates…
Added 4 hours ago
A&
Manager, Core Tax
Alvarez & Marsal
Calgary, AB
- Full-time
…design: we give people ownership and impact from day one, fuel development through real opportunity, and provide direct access to leaders who invest in our growth. Our culture celebrates…
Added 4 hours ago
PH
CCMG Genetic and Genomic Diagnostics Fellowship, Division of Genome Diagnostics, Department of Pathology and Laboratory Medicine - BC Children’s Hospital & BC Women’s Hospital
Provincial Health Services Authority
Vancouver, BC
- Full-time
…requirements and guidelines. You will participate in new test development and implementation, collaborate on division, hospital and provincial initiatives pertinent to laboratory genetics…
Added 4 hours ago
FI
Field Sales Representative
Federated Insurance Company of Canada
Mississauga, ON
- Full-time
…collaborate with Underwriting, Claims, Loss Prevention, and leadership teams to create exceptional client experiences and long-term partnerships. Backed by industry-leading training,…
Added 4 hours ago
A&
Director, Global Transaction Tax
Alvarez & Marsal
Toronto, ON
- Full-time
…design: we give people ownership and impact from day one, fuel development through real opportunity, and provide direct access to leaders who invest in our growth. Our culture celebrates…
Added 4 hours ago
A
Bilingual HR Advisor
ALS
Winnipeg, MB · Sudbury, ON · Thunder Bay, ON · CAN - ON - Sudbury
- Full-time
The HR Advisor works with the HR Manager to provide support in all areas of HR to an assigned client group. This role serves as a primary point of contact for managers, supervisors, and…

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 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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