Jobs in Canada

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Added 10 mins ago
B
Account Executive - SaaS (Base upto $85K, OTE $450K)
BoomerangFX
Mississauga, ON
- $65,000 to $85,000 CAD / year
- Full-time
Joining BoomerangFX is an opportunity to build your career alongside a growing global business. You will have meaningful responsibility, exposure to international markets and the…
Added 10 mins ago
IG
Field Sales Executive
Insight Global
Windsor, ON
- $75,000 to $80,000 CAD / year
- Full-time
Insight Global is seeking a driven Field Account Executive to develop new business and grow customer relationships for out client across the Windsor/Sarnia territory. This is a full-time…
Added 10 mins ago
Y
SaaS Sales Development Representative (SDR) - Lead Generation (B2B)
YuJa
Toronto, ON · North York, ON
- $60,000 to $70,000 CAD / year
- Full-time
This is an expansion role designed to support the continued growth and scaling of our Sales Development team. Our Sales Development team members are at the forefront of our growth,…
Added 10 mins ago
F
Inside Sales Representative
Financeit
Remote, Canada
- $50,000 to $60,000 CAD / year
- Full-time
- Remote
Reporting into the Sales Manager, this B2B role involves managing merchant relationships and dealing directly with the owners, finance managers and sales agents of businesses wishing to use…
Added 25 mins ago
V
Senior Security Engineer
Venn
Toronto, ON
- Full-time
Our founders both worked at Revolut before starting Venn and were raised by small business owners. Today more than 15,000 Canadian businesses run on Venn. We're the fastest-growing B2B…
Added 40 mins ago
S
HR Manager
Sidetrade
Calgary, AB
- Full-time
Four days per week on-site at our Calgary office
Added 40 mins ago
F
Inside Sales Representative
Financeit
Toronto, ON
- $50,000 to $60,000 CAD / year
- Full-time
Reporting into the Sales Manager, this B2B role involves managing merchant relationships and dealing directly with the owners, finance managers and sales agents of businesses wishing to use…
Added 40 mins ago
B
Sales Development Representative
BoomerangFX
Mississauga, ON
- Full-time
Applicants must have outbound sales experience
Added 1 hour ago
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Business Development Manager-Toronto
Digicast
Toronto, ON
- Full-time
The Business Development Manager – Toronto Market is responsible for driving new business, developing and nurture strategic relationships in the GTA, and positioning Digicast as the premier…
Added 1 hour ago
C
Account Executive - B2B Hardware Sales and Solutions
CareTek
Brampton, ON
- Full-time
…serving mid-market and enterprise clients across Ontario. Our business spans two connected revenue streams: hardware supply - laptops, desktops, servers, storage, networking and peripherals…
Added 2 hours ago
CP
Commercial Sales Associate
CertaPro Painters of Calgary & Central Alberta
Calgary, AB
- $50,000 to $100,000 CAD / year
- Full-time
We're looking for someone who is passionate about sales, delivering exceptional service to clients, and growing our business.
Added 2 hours ago
MC
Product Manager
Modern Campus
Canada
- Full-time
You will serve as the Product Owner for Agile development teams while also contributing to product strategy, roadmap planning, customer discovery, and commercial outcomes. This position…
Added 3 hours ago
S
HR Manager
Sidetrade
Remote, Canada
- Remote
Four days per week on-site at our Calgary office
Added 3 hours ago
R
Marketing Manager
Roshel
Brampton, ON
- Full-time
The role is responsible for developing and executing marketing strategies, supporting business development initiatives, coordinating industry events and campaigns, and ensuring alignment…
Added 3 hours ago
SE
Sales Representative
Surface Experts North Fort Worth
Saint-Paul, NB · St.-Paul, NB
- Full-time
Do you get excited about growing with a new business? Do you value autonomy and yet can thrive in accountability? At Surface Experts, we believe in a culture of caring for our employees and…
Added 4 hours ago
SP
Principal Applied AI Architect
Salesforce Partner Canada
Montreal, QC
- Full-time
…on customers’ own data and objects, using modern AI-assisted development tools. Turn a hypothesis into something a business sponsor can see and use within weeks, not…
Added 5 hours ago
J
Senior Director, Engineering - ICM
Jobgether
Canada
- Full-time
…Go-to-Market, and executive leadership, you will translate complex business opportunities into scalable technology solutions. You will also play a central role in developing future…
Added 5 hours ago
B
Customer Success Manager (Hybrid Vancouver)
Boomi
Vancouver, BC
- Full-time
…automation platform helps organizations power the future of business. At Boomi, you’ll work with world-class people and industry-leading technology. We hire trailblazers with an…
Added 6 hours ago
H
Sales Representative
Haystack
Canada
- Full-time
3+ years of full-cycle, new-business sales experience in B2B technology with a consistent track record of meeting or exceeding quota
Added 8 hours ago
C
Business Development Manager
CYGNVS
Toronto, ON
- Full-time
Based in or willing to work from Toronto, with the ability to be in-office 3–4 days per week
Added 8 hours ago
BH
Tech Lead - ToolHound
Beacon Holdings
Canada
- Full-time
…Our engineers go where the work is: embedded inside a single business, owning its technology end to end, and compounding its enterprise value quarter over…
Added 10 hours ago
Q
Revenue Operations Manager – Partner & Channel Operations
Quadient
Markham, ON
- $90,000 to $100,000 CAD / year
- Full-time
Our success in delivering innovation and business growth is inspired by the connections our diverse teams create every day, with our clients and each other.
Added 11 hours ago
EM
Director of Marketing
Enhanced Medical Nutrition
Toronto, ON
- Full-time
…to build upon and deploy the marketing strategy across all business areas (B2B2C). Reporting to the Chief Executive Officer (CEO), you will lead projects aimed at attracting and retaining…
Added 11 hours ago
Q
Revenue Operations Manager – Partner & Channel Operations
Quadient
Markham, ON
- $90,000 to $100,000 CAD / year
- Full-time
Our success in delivering innovation and business growth is inspired by the connections our diverse teams create every day, with our clients and each other.
Added 13 hours ago
DR
Outside Sales Representative - Precast Concrete
DMC Recruitment Group
Vancouver, BC
- Full-time
…conversation through quote, order and delivery. The role combines new business development, account management and technical product sales. You’ll work with contractors to understand what…

FutureSight

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

Canada

Full-time

Apply on LinkedIn 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.

Apply on LinkedIn About employer

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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Work requirements

Jobs in Canada