GM, Insurance in Canada Creek, Nova Scotia at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a GM, Insurance based in Canada.

This is a senior entrepreneurial leadership role responsible for building and scaling a new insurance vertical from the ground up within a fast-growing digital health and pet care ecosystem. You will act as the general manager and business owner of the insurance line, defining its strategy, operating model, and long-term growth trajectory. The role combines strategic vision with hands-on execution across product, partnerships, operations, and financial performance. You will lead the expansion of a regulated, multi-state insurance offering, ensuring compliance while delivering a seamless customer experience. This position requires strong commercial instincts, deep analytical ability, and comfort operating in complex, fast-evolving environments. It is ideal for a leader who thrives on building new businesses, owning full P&L accountability, and scaling high-impact consumer offerings.

In this role, you will be responsible for building, launching, and scaling the insurance business line end-to-end, with full ownership of strategy, execution, and financial performance.

• Define and execute the end-to-end strategy for the insurance vertical, including launch, growth, and long-term scaling across markets
• Own the business plan, including revenue model, pricing strategy, unit economics, acquisition, retention, and profitability targets
• Lead the expansion strategy to enable multi-state and nationwide insurance availability, ensuring regulatory and operational readiness
• Build and manage relationships with insurance carriers, brokers, TPAs, underwriting partners, and other external stakeholders
• Design and optimize the customer journey across quoting, onboarding, claims education, renewals, and engagement
• Own full P&L accountability, including revenue, CAC, margins, partner economics, and operating costs
• Collaborate cross-functionally with product, engineering, marketing, legal, finance, and CX teams to embed insurance into the broader ecosystem
• Develop dashboards, reporting frameworks, and operating rhythms to track business performance and drive decision-making
• Identify and execute new growth opportunities across acquisition channels, partnerships, and existing customer base

The ideal candidate brings strong experience building and scaling insurance or regulated consumer businesses, with full ownership of a business line or P&L.

• 8+ years of experience in insurance, fintech, healthcare, marketplace, subscription, or regulated consumer businesses
• Proven track record of owning a P&L, business unit, or product line with measurable revenue and margin responsibility
• Strong understanding of insurance models, including carrier partnerships, brokerage/agency structures, claims, underwriting, and compliance frameworks
• Experience scaling a business or product from early-stage launch to meaningful revenue growth
• Strong analytical and commercial mindset with the ability to translate data into strategic decisions
• Excellent cross-functional leadership skills across product, legal, operations, finance, and marketing teams
• Strong understanding of pricing, unit economics, conversion optimization, and retention strategies
• Ability to operate effectively in regulated, ambiguous, and fast-changing environments
• Strong communication and executive presence, with the ability to influence senior stakeholders
• Entrepreneurial mindset with a strong bias toward ownership, execution, and building from scratch

• Competitive base salary range of USD $175,000 – $250,000 depending on experience and location
• Equity participation and performance-based incentives
• Fully remote-first working model across eligible locations including Canada
• Comprehensive health, dental, and vision insurance coverage
• Flexible paid time off policy
• Opportunity to build and own a new, category-defining insurance business line
• High executive visibility and strategic influence within a rapidly scaling organization
• Mission-driven environment focused on improving access to pet healthcare and insurance