Job Overview
Location
Toronto
Job Type
Full-time
Category
Customer Success
Date Posted
May 17, 2026
Full Job Description
đź“‹ Description
- • Own end-to-end deployment of AI agents for enterprise customer accounts, managing complex, multi-stakeholder rollouts from kickoff to sustained automation performance
- • Serve as the primary point of contact for customer deployment success, ensuring seamless integration of AI agents across helpdesk platforms including Zendesk, Gorgias, or similar systems
- • Diagnose operational bottlenecks in customer CX workflows—such as ticket routing logic, automation health, escalation failures, and knowledge base gaps—and drive actionable fixes
- • Maintain consistent, proactive communication with customers through written updates, verbal briefings, and Slack threads, ensuring transparency on timelines, blockers, and progress without requiring follow-ups
- • Monitor key automation metrics including automation rate, deflection rate, and escalation patterns; anticipate performance dips before customers report them and present data-backed recommendations for improvement
- • Co-lead strategic accounts with senior team members, gradually assuming full ownership of deployments after a 30-day shadowing period
- • Manage customer expectations with authority: enforce scope boundaries, push back on unplanned feature requests, and preserve relationships during high-pressure moments
- • Document all deployment progress, configuration changes, and blocker resolutions in clear, actionable formats accessible to internal teams and customers
- • Feed operational insights gathered across customer accounts back to the product team to inform product improvements, prioritization, and feature development
- • Enable and guide customers new to AI tools by demonstrating practical applications, troubleshooting workflow issues, and helping them adopt AI as a natural extension of their operations
- • Maintain daily accountability for every assigned account, ensuring continuous momentum and preventing stagnation through structured follow-ups and proactive escalation
- • Collaborate with cross-functional teams including engineering, product, and customer success to align deployment goals with technical capabilities and product roadmap
- • Participate in internal knowledge-sharing practices such as demo days and Slack threads, contributing and learning from team members’ AI workflows and automation best practices
- • Apply deep CX operations expertise to interpret customer behavior, identify systemic inefficiencies, and translate them into AI agent enhancements that improve customer experience
- • Balance startup speed with high standards: deliver high-quality deployments under tight timelines without compromising on configuration accuracy, documentation, or customer satisfaction
- • Operate as a co-leader within the deployment team—sharing workload, mentoring peers, and strengthening team processes through collective ownership
- • Work remotely as part of a globally distributed team focused on redefining customer experience through persistent, learning AI agents
🎯 Requirements
- • 5+ years in customer experience operations, support operations, implementation, or CX agency work
- • Deep fluency with helpdesk platforms such as Zendesk, Gorgias, or similar
- • Proven understanding of ticket lifecycle, routing logic, automation health, and escalation flows in support operations
- • Strong project management skills with ability to break down complex workflows into actionable plans and keep multiple workstreams aligned
- • Active, practical experience using AI tools in daily workflows and ability to guide customers new to AI
- • Excellent written and verbal communication skills under pressure, with ability to make account status visible without prompting
🏖️ Benefits
- • Competitive salary plus opportunity for equity or stock grants
- • Learning budget for personal and professional growth
- • Premium AI tool subscriptions (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus quarterly budget for new tools
- • Remote work flexibility as part of a globally distributed team
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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