Job Overview
Location
Toronto
Job Type
Full-time
Category
Product Manager
Date Posted
May 17, 2026
Full Job Description
đź“‹ Description
- • Own end-to-end deployment outcomes for strategic enterprise accounts, including automation rates, resolution rates, and time-to-value for AI agents across support, shopping, voice, and social channels.
- • Deploy AI agents directly within customer environments, diagnosing and resolving blockers that are technical, operational, or stakeholder-driven, without relying on engineering translation.
- • Turn field insights from deployments into actionable platform improvements that scale across all customers, closing the loop between on-the-ground experience and product development.
- • Collaborate directly with enterprise customer experience leaders to design, align, and execute AI transformation roadmaps that redefine their CX infrastructure.
- • Build and refine agent capabilities that operate seamlessly across multiple platforms and interaction channels, ensuring consistency, accuracy, and empathetic user experiences.
- • Design and implement evaluation systems including QA suites, automated testing protocols, and performance monitoring dashboards to measure agent effectiveness.
- • Lead full product launch cycles from internal testing through general availability, including customer enablement, training, and adoption strategy.
- • Demonstrate products directly to customers and co-sell alongside sales teams, becoming a trusted advisor known by name within customer communities.
- • Write clear documentation, create demo workflows, and measure key success metrics to drive adoption and continuous improvement.
- • Operate as a forward-deployed product manager embedded with clients, acting as the bridge between customer needs and platform innovation.
- • Leverage AI-native workflows using tools like Claude, Cursor, and other AI platforms to automate your own processes, prototype solutions, and optimize deployment efficiency.
- • Scope complex integrations including webhooks, OAuth flows, and API connections independently, without requiring engineering support to interpret requirements.
- • Identify gaps in customer workflows and translate them into prioritized product features that solve real, observed problems in customer experience operations.
- • Drive organizational change by advising CX leaders on process optimization, team structure, and transformation strategy to enable successful AI adoption.
- • Act as a product advocate within customer accounts, building relationships and trust to ensure long-term success and feedback loops into the platform.
- • Maintain high standards for product quality and customer impact while operating at startup speed in a distributed, remote environment.
- • Participate in internal demo days and knowledge-sharing Slack threads to contribute to and learn from team-wide AI workflow innovations.
🎯 Requirements
- • 5+ years in product management, solutions engineering, forward deployment, or technical account ownership
- • AI-native mindset with proven experience using AI tools like Claude, Cursor, and similar platforms to build personal workflows
- • Ability to scope and implement integrations such as webhooks, OAuth flows, and complex APIs without engineering assistance
- • Hands-on experience diagnosing and resolving deployment issues across technical, operational, and stakeholder dimensions
- • Deep understanding of customer experience (CX) challenges and what constitutes excellent CX from within an enterprise environment
- • Comfort advising CX leaders on organizational design, process optimization, and transformation strategy
🏖️ Benefits
- • Competitive salary plus equity or stock grant opportunities
- • Learning budget for professional development and new tools
- • Premium AI tool subscriptions (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus quarterly budget for additional tools
- • Remote-first environment with preference for Canada and Latin America
Skills & Technologies
About Siena AI.
Siena AI is a customer experience (CX) platform designed for e-commerce brands. It combines human empathy with AI-driven automation to enhance customer support across various channels, including chat, email, SMS, and social media. The platform allows businesses to create personalized AI agents that reflect their brand's voice and tone, enabling seamless and empathetic interactions with customers. Siena AI integrates with existing e-commerce systems, providing real-time access to order information, product details, and customer data to resolve inquiries efficiently. It also offers features like reviews management, shopping assistance, and memory capabilities to personalize customer interactions. Siena AI aims to help brands scale their customer support operations while maintaining a high level of customer satisfaction.
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