Top Tech Jobs & Startup Jobs in Toronto

Supports the CEO and leadership team by managing calendars, travel, communications, meetings, and follow-up. Maintains NYC office operations, vendors, facilities, supplies, recruiting coordination, team events, and company culture initiatives. The role also involves automating workflows, documenting processes, handling confidential information, and adapting responsibilities as the company grows.

Lead actuarial client engagements involving feasibility studies, pricing, reserving, renewal assessments, and captive risk analysis. Translate actuarial findings into recommendations on retention, funding, collateral, and capital. Review external actuarial work, maintain rigorous documentation, and develop reusable Excel, Python, and R tools. Collaborate with Product and Engineering to improve risk simulation capabilities, mentor colleagues, support hiring, and contribute to commercial discussions.

Own monthly and quarterly close activities for captive insurance clients, including journal entries, reconciliations, premium and loss accounting, intercompany activity, and financial statements. Serve as a client finance contact, support audits and regulatory filings, document processes, and partner with technology teams to automate accounting workflows. The role requires insurance accounting expertise, strong communication, client presence, and a systems-oriented approach.

Owns significant parts of a regulated insurance platform end to end, from discovering ambiguous customer problems through architecture, implementation, production deployment, and adoption. Establishes technical direction, builds full-stack systems, integrates AI and agentic workflows responsibly, collaborates directly with clients and business users, shapes the product roadmap, and mentors engineers. The role requires strong product judgment, startup ownership, pragmatic architecture decisions, and 5+ years of production software experience.

Risk Analyst supporting insurance and reinsurance clients through quantitative analysis, financial modeling, scenario analysis, stress testing, and market research. The role develops models for insurance transactions and captive structures, analyzes claims and investment scenarios, supports reinsurance arrangements, prepares client materials, and maintains proprietary risk analytics tools. Candidates should demonstrate strong financial, mathematical, statistical, data manipulation, communication, and analytical skills.

Generate qualified sales pipeline through targeted outbound prospecting to CFOs, risk managers, and insurance broker principals. Responsibilities include account research, multi-channel outreach via email, phone, and LinkedIn, lightweight qualification, CRM maintenance, clean handoffs to Account Executives, and reporting market feedback. The role requires a tenacious, analytical, entrepreneurial self-starter who can learn captive insurance and financial services concepts quickly while consistently meeting activity and pipeline targets.

Generate new business through outbound prospecting, build and manage a sales pipeline, own the full enterprise sales cycle, and close complex deals with C-suite executives. Translate customer needs into financial and strategic value, collaborate with risk specialists on bespoke solutions, and consistently exceed sales quotas. The role requires entrepreneurial ownership, executive presence, intellectual agility, and experience selling in complex B2B environments such as insurance, financial services, fintech, or enterprise SaaS.