Job Overview
Location
Toronto
Job Type
Full-time
Category
Customer Success
Date Posted
May 17, 2026
Full Job Description
đź“‹ Description
- • Own the end-to-end technical and commercial health of key customer accounts, ensuring AI agents are deployed, configured, and performing optimally across customer touchpoints.
- • Diagnose and resolve automation performance issues independently—without escalating to engineering—by analyzing configurations, integration logs, and agent behavior patterns.
- • Serve as the primary point of contact for customers, earning trust through deep product fluency and proactive issue resolution that reduces churn and increases satisfaction.
- • Conduct regular business reviews with customer stakeholders, presenting data-driven insights on automation rates, resolution rates, and customer experience metrics to guide strategic decisions.
- • Partner closely with the deployment team during onboarding to ensure seamless handoffs, accurate setup, and clear success criteria for each new account.
- • Identify expansion opportunities by recognizing adoption signals, usage growth, and unmet needs, then articulate additional value without sounding sales-driven.
- • Translate real-time customer feedback into structured, actionable product insights that inform roadmap priorities and feature improvements.
- • Monitor account health through quantitative metrics (ARR, renewal risk, engagement trends) and act before issues escalate, demonstrating commercial awareness and foresight.
- • Maintain deep technical fluency in SaaS integrations, API connections, and AI agent workflows, enabling you to guide customers through complex configurations independently.
- • Build long-term relationships where customers actively seek your input, not just during crises but for strategic advice on optimizing their AI-powered customer experience.
- • Enable customers who are new to AI by demonstrating practical use cases, sharing workflow patterns, and helping them adopt AI tools confidently within their own teams.
- • Stay ahead of industry trends in AI-driven customer experience, leveraging your own AI ecosystem to continuously refine your approach and share best practices internally.
- • Document deployment patterns, common failure modes, and optimization tactics to build internal knowledge bases that elevate the entire team’s effectiveness.
- • Balance startup-speed execution with high standards, adapting quickly to changing priorities while maintaining rigorous attention to detail in every customer interaction.
- • Actively participate in internal demo days and Slack knowledge-sharing threads, contributing your AI workflows and learning from peers across the distributed team.
- • Drive retention by proving consistent value through measurable outcomes, not just service delivery—turning satisfied customers into advocates and long-term partners.
- • Work remotely with a globally distributed team, coordinating across time zones to deliver timely, high-quality support and strategic guidance to customers worldwide.
- • Embrace a culture of direct, constructive feedback—giving and receiving it with clarity to ensure continuous improvement in both product and process.
- • Use company-provided premium AI tools (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) daily to enhance your efficiency, automate repetitive tasks, and model best practices for customers.
- • Contribute to shaping the future of customer experience by being on the frontlines of how AI agents remember, learn, and act across channels.
🎯 Requirements
- • 5+ years in technical account management, customer success engineering, or a hybrid technical/commercial role
- • Proven experience in SaaS, CX platforms, or e-commerce environments
- • Technically fluent: ability to read configurations, troubleshoot integrations, and diagnose deployment issues without escalation
- • Commercial awareness: understanding of ARR, renewal risk, and expansion signals
- • Active, hands-on use of AI tools in daily workflow and ability to guide customers new to AI
- • Proactive data-driven behavior: interpreting metrics to anticipate issues and drive action before customer outreach
🏖️ Benefits
- • Great salary plus equity or stock grants
- • Learning budget for tools, courses, and professional development
- • Premium AI tool subscriptions (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable)
- • Quarterly budget for new AI tools
- • Opportunity to work with a globally distributed team at the bleeding edge of AI and customer experience
- • Mission-driven culture focused on building something unprecedented in customer experience technology
Skills & Technologies
Remote
Degree Required
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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