Top Tech Jobs & Startup Jobs in Toronto

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.

Lead development and consolidation of Jerry.ai's AI agent platform, owning roadmap to rollout. Design prompt strategies, evaluation frameworks, guardrails, and API/system architecture. Partner with engineers and OpenAI to deploy voice and workflow automation, drive experiments to improve automation rates, accuracy, and customer satisfaction, and establish AI best practices across the org.

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.

Embed within a core business area to define problems, build metrics, run analyses and experiments, create reports, surface insights, and drive data-informed product, growth, AI, or partnership outcomes end-to-end.

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.

Embedded within a core business area, define analytics problems, build metrics/reports, run analyses and experiments, surface insights, and drive data-informed decisions end-to-end with stakeholders.

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.

Lead Jerry's editorial strategy and execution for SEO and AEO across jerry.ai and external platforms. Design and operate an AI-native brief-to-publish pipeline, set YMYL accuracy and E-E-A-T standards, manage quality gates and prompt libraries, track search and AI citation presence, and drive organic traffic and conversion targets while managing a small team and freelance bench.

Embed on a core business team to define problems, build metrics/reports, run analyses and experiments, and drive data-informed recommendations end-to-end to improve growth, product, AI/automation, or partnerships.