Jobs in Canada

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Added 8 mins ago
RL
Account Manager – Niagara Region & GTA West
RENO Lighting
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Collaborate with Inside Sales, Operations, and Customer Service to resolve issues quickly and prevent recurrence.
Added 8 mins ago
VG
Account Coordinator
Valentini Group
Oakville, ON
- Full-time
…and strategy. You’ll manage content calendars, support and lead content production, monitor performance, and use insights to help strengthen our clients’ social…
Added 8 mins ago
EC
Profit Centre Manager
Emco Corporation: Plumbing, HVAC, Waterworks, Industrial, Irrigation, Fire Protection
Sudbury, ON · Greater Sudbury, ON
- Full-time
Our purpose is to help build stronger communities by delivering the products, expertise, and service that support critical systems in residential, commercial, industrial, and infrastructure…
Added 9 mins ago
Seasonal - Sales Associate-Retail
Roots
Toronto, ON
…brand’s legacy. If you bring passion to everything you do, lead with integrity, and believe in the power of collaboration to drive growth, we’d love to have you on our…
Added 9 mins ago
VC
Vans: Assistant Gérant - Premium Outlets Montreal
VF Corporation
Mirabel, QC
- $23.6 to $31.2 CAD / hour
- Full-time
As the Assistant Store Manager, you will lead, develop, and motivate a team of Brand Advocates to deliver consistent, best-in-class customer experience that reflects our brand values and…
Added 9 mins ago
V
Vans: Assistant Gérant - Premium Outlets Montreal
Vans
Mirabel, QC
- $23.6 to $31.2 CAD / hour
- Full-time
As the Assistant Store Manager, you will lead, develop, and motivate a team of Brand Advocates to deliver consistent, best-in-class customer experience that reflects our brand values and…
Added 9 mins ago
Ecommerce Operations Manager
Vacances Air Canada Vacations / Air Canada Rouge
Montreal, QC
Serve as the primary Ecommerce Operations partner across Marketing, Product, Merchandising, Customer Service, Analytics and other business teams.
Added 9 mins ago
O
Supervisor, Property Operations
OMERS
Toronto, ON · Scarborough Town Centre
- Full-time
…guests - overseeing preventative maintenance, contractors, service requests, energy management and emergency response, while supporting property projects and sustainability…
Added 9 mins ago
M
Sr. Specialist (Five 9)
McKesson
Mississauga, ON
- Full-time
Build and optimize call routing strategies, IVR workflows, self-service capabilities, and omnichannel customer experiences.
Added 9 mins ago
P4
Property Manager
Pier 4 Ltd
Dartmouth, NS
- Full-time
…residential portfolio across Nova Scotia. This is an opportunity to lead property operations, develop high-performing teams, strengthen resident communities, and directly influence the…
Added 23 mins ago
EC
Future Leaders Program – Management Trainee
Emco Corporation: Plumbing, HVAC, Waterworks, Industrial, Irrigation, Fire Protection
Corner Brook, NL
- $52,500 CAD / year
- Full-time
Phase 1: Warehouse and Customer Service (12 Months)
Added 23 mins ago
MM
Manager, Regulatory & Government Affairs
Mitsubishi Motor Sales of Canada, Inc.
Mississauga, ON
- $105,000 to $115,000 CAD / year
- Full-time
This position is the lead and sole managerial position for regulatory and government affairs at MMSCAN. The manager must ensure technical compliance with all required government safety,…
Added 23 mins ago
J
CEO - B2B2C Insurtech
Toronto, ON
- Full-time
Insurance is one of Canada's largest and most established industries, yet the customer relationship remains largely transactional and reactive.
Added 23 mins ago
C
Director Supply Chain Strategy
Ciena
Ottawa, ON
- Full-time
This leader will translate business growth objectives, product strategy, customer requirements, market dynamics, and external supply-chain trends into an integrated global supply chain…
Added 23 mins ago
SD
Pharmacist, Hourly Part Time Evening
Shoppers Drug Mart
Winnipeg, MB
- Part-time
Commitment to providing exceptional customer service
Added 23 mins ago
SD
Pharmacist, Hourly Part Time Day
Shoppers Drug Mart
Toronto, ON
- Part-time
Commitment to providing exceptional customer service
Added 23 mins ago
SD
Pharmacist, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Toronto, ON
- Full-time
Commitment to providing exceptional customer service
Added 23 mins ago
SD
Front Store Manager, Salaried Full Time Day Greenlight Requisition
Shoppers Drug Mart
Edmonton, AB
- Full-time
…Store Manager leads staff in providing excellent Front Store customer service, manages all process and procedures utilizing financial resources and ensures store objectives are…
Added 23 mins ago
B
Experts, service-conseil | Client Success Experts
Bloom
Montreal, QC
- Full-time
(Account Manager, Senior Account Manager, Account Supervisor, Client Success Specialist, Customer Success Manager, Account Director, Senior Project Manager, Product Lead, etc.)
Added 23 mins ago
A
Ingénierie en Chef - Systèmes avion (train d’atterrissage, freins, air, carburant) / Chief Engineering - Aircraft Systems (Landing Gear, Brakes, Air, Fuel)
Airbus
Montreal, QC · Mirabel, QC
- Full-time
Bien-être / santé: Programme d’Aide aux Employé.e.s (PAE), programme de rabais, service médical sur site, accès à un service de navette publique entre Laval (station de métro Montmorency)…
Added 23 mins ago
W
(CAN) Front End Team Lead
Walmart
Abbotsford, BC
- Full-time
…associates through teaching and training. Ensure a high level of customer service while ensuring task…
Added 23 mins ago
Automation Team Lead
Riverside Natural Foods Ltd.
Toronto, ON
The automation team lead will be responsible for strategic planning, decision-making, and supervising the maintenance and troubleshooting of automated systems to ensure their proper…
Added 23 mins ago
L
Legal Product Consultant
Litera
Toronto, ON · Canada-Toronto, ON-Office
- Full-time
Lead onboarding and adoption programs for law firms implementing Litera’s AI-powered products designing custom integration strategies that align with clients’ existing legal workflows and…
Added 24 mins ago
CB
Full time Baker
COBS Bread
Peterborough, ON
- Full-time
…product, the development of our people, and our warm and friendly customer…
Added 38 mins ago
JG
Pega Technical Lead
J&M Group
Toronto, ON
- Full-time
Pega Customer Service, Smart Dispute, and Smart Investigate

CEO - B2B2C Insurtech

Toronto, ON, Canada

Full-time

Apply on jobs.lever.co

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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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Apply on jobs.lever.co

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

Visa sponsorship

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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