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Seasonal - Sales Associate-Retail
Roots
Toronto, ON
…The main objective of this position is to provide exceptional service to customers and build relationships with them. The goal is to develop customers for…
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VC
Vans: Assistant Gérant - Premium Outlets Montreal
VF Corporation
Mirabel, QC
- $23.6 to $31.2 CAD / hour
- Full-time
…rentabilité du magasin, en misant sur l’excellence des opérations, du service à la clientèle, du marchandisage et de l’engagement…
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Vans: Assistant Gérant - Premium Outlets Montreal
Vans
Mirabel, QC
- $23.6 to $31.2 CAD / hour
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Retail Sales & Delivery Associate
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Edmonton, AB
…Saskatchewan, Alberta, B.C., and Yukon. At FIKA we provide exceptional service in a variety of welcoming, intuitive, and diversified store environments, this has allowed The FIKA Company…
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Strong customer/patient service with the ability to relate to patients and clients even in stressful situations
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Sales Associate-Retail
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Ottawa, ON
Deliver exceptional customer service by confidently engaging and assisting customers.
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ASSISTANT MANAGER
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Repentigny, QC
…runs smoothly and that your team provides the best possible customer service. When you’re working as acting manager, your tasks will include meeting overall goals, maintaining our corporate…
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MANAGER
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…runs smoothly and that your team provides the best possible customer service. Your role will involve meeting overall objectives and maintaining our corporate standards for customer service,…
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JUNIOR ASSISTANT MANAGER
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Keep the store running smoothly and ensure your team provides outstanding customer service;
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JUNIOR ASSISTANT MANAGER
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CASHIER
Boutique La Vie En Rose
Mirabel, QC
You have previous customer service experience;
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Administrative Assistant
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Vancouver, BC
- Full-time
Strong verbal and written communication skills, with a polished, professional and customer-focused presence
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Keep the store running smoothly and ensure your team provides outstanding customer service;
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ACTING MANAGER
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Ottawa, ON
…runs smoothly and that your team provides the best possible customer service. Your role will involve meeting overall objectives and maintaining our corporate standards for customer service,…
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Job Location: Fully on-site (5 days in office) - based in Montreal QC · Must Have(s)
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Vancouver, BC
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Future Leaders Program – Management Trainee
Emco Corporation: Plumbing, HVAC, Waterworks, Industrial, Irrigation, Fire Protection
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Phase 1: Warehouse and Customer Service (12 Months)

CEO - B2B2C Insurtech

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
Working alongside one of Canada's leading insurers, we're launching a B2B2C technology company with the potential to reach millions of Canadians.

Insurance is one of Canada's largest and most established industries, yet the customer relationship remains largely transactional and reactive.

We believe advances in AI and software create an opportunity to fundamentally change this relationship. Our ambition is to build a product that delivers ongoing value to consumers while creating meaningful commercial value for enterprise partners.

We're looking for an entrepreneurial operator to lead this venture from day one. You'll work alongside Simple Ventures and established industry partners to bring the product to market, build the commercial model, and scale the business, with real ownership and SV as a highly engaged partner.

About you

You are an operator who knows how to introduce new products into established industries.

You have a strong ability to win over large organizations, turn early pilots into lasting partnerships, and build the operations needed to support growth. You are equally comfortable securing major deals and making sure the business can deliver on them.

What you’ll need:

Background

Experience: 10+ years of experience, most recently executive-level experience, with a proven track record of success
B2B Experience: Experience securing and managing partnerships with large organizations, navigating complex sales cycles, and turning early opportunities into long-term commercial relationships.
B2C Experience: Experience building or scaling consumer-facing products or services, with a strong understanding of customer acquisition, engagement, and retention.
Industry Expertise: Strong preference for experience in insurance, property technology, home services, or adjacent technology-enabled service industries, with a demonstrated ability to navigate complex industry ecosystems.
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 B2B2C insurtech venture by building commercial models and securing enterprise partnerships. They will act as the primary face of the business, driving product-market fit and ensuring long-term operational success.

Requirements

Candidates must have over 10 years of executive-level experience with a proven track record in both B2B partnership management and B2C product scaling. Strong industry expertise in insurance or technology-enabled services is preferred, alongside a demonstrated ability to navigate complex sales cycles.

Skills

B2B Sales
B2C Strategy
Executive Leadership
Strategic Planning
Partnership Management
Product Launch
Commercial Modeling
Financial Acumen
Decision Making
Customer Experience Design
Operations Management
Insurtech
AI Strategy
Stakeholder Management
Entrepreneurship

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Keywords

CEO
Insurtech
B2B2C
Simple Ventures
Startup
Venture Building
Insurance
AI
Software
Commercial Model
Partnerships
Customer Acquisition
Retention
Property Technology
Home Services
Executive Leadership
Unit Economics
Seed Investment
Operations
Brand Management
Financial Analysis
Strategic Planning
Entrepreneurial
Growth
Market Entry

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Jobs in Canada