GM, Insurance

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

Requirements:

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

Benefits:

• 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