Top Tech Jobs & Startup Jobs in Toronto

Lead Jerry’s organic growth and content strategy across its website and external channels. Own SEO and AEO performance, content roadmaps, customer acquisition targets, and AI citation visibility. Design an AI-native brief-to-publish workflow with prompts, human editing, QA gates, sourcing, and editorial standards. Manage one direct report, AI agents, freelancers, and content quality for highly accurate insurance and financial content.

Lead end-to-end performance creative: ideate, script, produce, edit, and iterate ads across paid social, CTV, and emerging channels. Translate performance data into creative direction, manage agencies and production partners, and leverage AI tools to accelerate workflows while elevating visual quality and brand.

Lead end-to-end development and scaling of Jerry.ai's customer-facing Agentic AI platform. Define roadmap, partner with engineering on prompt strategies, evaluation frameworks, and guardrails, drive experimentation to improve automation rates and quality, and coordinate with partners (e.g., OpenAI) to deploy new model and voice capabilities.

Own and launch new 0-to-1 product bets (home, motorcycle, RV, boat, property-tax savings). Rapidly learn domains, prioritize using quantitative and qualitative insights, build and ship experiments, iterate on product-market fit, and scale successful offerings while managing regulatory and operational complexity.

Lead consolidation and strategic direction of Jerry.ai's AI platform, unifying prompt assets, prioritizing chatbot technical work, managing vendor relationships (e.g., OpenAI), and coordinating engineering, data, and operations to deliver scalable, production-grade agentic AI products and platform architecture.

Lead development and scaling of a customer-facing agentic AI platform using LLMs and agents. Define prompt strategies, evaluation frameworks, and guardrails; translate technical architecture to stakeholders; run experiments to improve automation, answer quality, and customer satisfaction; and partner with OpenAI on voice and workflow model integrations.

Lead end-to-end development and scaling of an agentic AI platform that automates customer sales and service. Define prompt strategies, evaluation frameworks, guardrails, and API/system architecture; partner with engineering and OpenAI; run experiments to improve automation rates, answer quality, and customer satisfaction; translate technical work across the organization.

Lead the end-to-end development and scaling of Jerry.ai's AI agent platform. Own roadmap, partner with engineering on prompt strategies, evaluation frameworks, and guardrails. Drive experiments to improve answer quality, automation rates, and customer satisfaction. Serve as technical translator, establish AI best practices, and work with partners like OpenAI to deploy voice models and workflow automation.

Lead product development for new consumer-facing bets (home, motorcycle, RV, boat, non-insurance features). Rapidly learn domains, prioritize using quantitative and qualitative insights, ship 0-to-1 products, iterate on feedback, and scale to product-market fit.

Own and evolve Jerry.ai's AI platform: consolidate prompts from six locations onto a unified system, prioritize chatbot technical work, drive architecture and emerging-technology decisions (voice/computer use), manage the OpenAI relationship, and coordinate cross-functional teams to deliver scalable production-grade AI features while keeping current systems running.