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- $23.6 to $31.2 CAD / hour
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CEO - B2B FinTech
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CEO - B2B FinTech

Toronto, ON, Canada

Full-time

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Job details

Job type: Full-time
Experience: Experience: 10+ years of experience, most recently executive-level experience, with a proven track record of success
Posting language: English
Posted: Nov 11, 2026

Original job description

About Us

We founded Simple Ventures with the mission of building great Canadian companies. Our thesis is simple: Canada is overlooked and under-appreciated. Most companies around the world ignore Canada because of perceived market size, regulation, language, and powerful oligopolies. As a result, Canadians miss out.

But we know better. Canada is a top 10 global economy with many of the same consumer and business pain points as other markets. This creates an opportunity to bring the best product ideas to Canada - to see what’s working around the world and be first to execute for Canadians.

We’re funded and supported by Canada’s top leaders including the founders of Wealthsimple, Shopify, Ada, MindBeacon and many more. We are always looking for talented leaders to partner with!

We identify and vet new company concepts that we have high conviction should be built and scaled in Canada. Our building philosophy is pragmatic. We look for concepts that have positive unit economics and that have a credible path to profitability with an initial Seed investment. Once we have conviction in a new venture concept, we look for a talented operator to partner with to build and scale the company with!

We are recruiting a CEO for our next venture.

The Opportunity
We are launching a B2B fintech company with a simple mission: help Canadian businesses navigate complex risks with greater clarity, confidence, and control.

Today, this category is dominated by traditional intermediaries, fragmented services, manual workflows, and limited transparency. Businesses often struggle to access the expertise, information, and support they need to make important decisions, despite the significant financial consequences involved.

We believe a modern, technology-enabled and customer-centric approach can fundamentally improve how businesses manage risk, delivering greater transparency, better service, and stronger long-term customer relationships in a large and established market.

This role is best suited for an entrepreneurial, commercially driven operator who is excited to build and scale a company from day one, with real ownership and Simple Ventures as a highly engaged partner.

About you
You are a sales-driven leader who knows how to win customers and build trust in complex B2B markets. You have a track record of securing major accounts, driving revenue growth, and building high-performing sales teams. You are equally comfortable winning business yourself and developing the processes and teams to do it consistently.

What you’ll need:

Background

Experience: 10+ years of experience, most recently executive-level experience, with a proven track record of success
Commercial Expertise: Experience building and scaling B2B sales, winning complex customers, and establishing repeatable go-to-market strategies.
Experienced radical accountability: Experience in a fast-growing environment and an understanding of the existential threats of the situation with limited resources.
Track Record of Success: Demonstration of intellectual curiosity, extreme levels of accountability, and an ability to be incredibly decisive.
Customer Experience: Obsession with designing and delivering an exceptional customer experience.
Brand: A distinct view of being the "brand owner" and the face of the business, a comfortability in pitching the business to customers, partners and stakeholders such as the Press.

Behavioural Competencies

Action Orientation: You readily take action on new opportunities with a sense of urgency, high energy, and enthusiasm. You display a can-do attitude, and step up to handle tough issues.
Resiliency: You are confident under pressure, and maintain a positive attitude despite setbacks or adversity. You are able to grow from hardships, and manage crises effectively.
Communicates Effectively: You are effective in a variety of communication settings: one-on-one, small and large groups, or among diverse styles and position levels.
Drives Vision and Purpose: You create organization-wide energy and optimism for the future, articulating your visions in a way that are positive and that everyone can relate to. Creates milestones and symbols to rally support behind the vision and motivate others into action.
Drives Results: You persist in accomplishing objectives and exceeding goals despite obstacles and setbacks, while also helping others to achieve results.
Financial Acumen: You use financial analysis and understanding of key indicators to generate, evaluate, and act on strategic options and opportunities, while integrating quantitative and qualitative information to draw accurate conclusions.
Decision Quality: You make sound and timely decisions that keep the organization moving forward, even in the absence of complete information. You consider all relevant factors and rely on a mixture of analysis, wisdom, experience, and judgment when making decisions.

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More about this job

Responsibilities

The CEO will lead the launch and scaling of a new B2B fintech company focused on risk management for Canadian businesses. This role involves driving revenue growth, building high-performing sales teams, and acting as the primary face of the brand to stakeholders.

Requirements

Candidates must have 10+ years of executive-level experience with a proven track record in B2B sales and go-to-market strategy. The role requires an entrepreneurial leader with strong financial acumen, decisive judgment, and the ability to operate effectively in a fast-growing environment.

Skills

B2B Sales
Strategic Planning
Revenue Growth
Leadership
Financial Acumen
Decision Making
Go-to-market Strategy
Customer Experience
Brand Management
Risk Management
Entrepreneurship
Team Building
Communication
Accountability
Resiliency

Visa sponsorship

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Keywords

FinTech
B2B
CEO
Startup
Venture Building
Sales Strategy
Risk Management
Revenue Growth
Go-to-market
Executive Leadership
Financial Analysis
Unit Economics
Seed Investment
Customer Experience
Brand Ownership
Accountability
Strategic Planning
Business Development
Market Expansion
Entrepreneurial

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