Job Overview
Location
Toronto
Job Type
Full-time
Category
Software Engineer
Date Posted
May 17, 2026
Full Job Description
đź“‹ Description
- • Embed as the technical lead within strategic customer deployment pods, collaborating with Deployment Managers and Forward Deployed Product Managers to resolve complex technical barriers in real-time customer environments.
- • Diagnose and resolve integration failures across helpdesk and customer experience platforms including Zendesk, Gorgias, and similar systems, focusing on API integrations, webhook misconfigurations, and automation logic failures.
- • Configure, test, and iterate on AI-powered agent behaviors within live customer environments, ensuring agents remember interactions, maintain context across channels, and deliver empathetic, persistent customer experiences.
- • Own the end-to-end technical onboarding of new accounts: establishing live integrations, ensuring data syncs are operational, and configuring initial automations tailored to the customer’s stack.
- • Build custom, account-specific automations and integrations that extend beyond out-of-the-box platform capabilities, often bridging gaps between e-commerce platforms like Shopify and CX systems via REST APIs.
- • Identify recurring technical patterns across multiple deployments and surface actionable insights to engineering and product teams to drive platform enhancements, reducing the need for one-off fixes.
- • Participate in technical scoping during late-stage sales cycles to assess feasibility of customer requirements, aligning technical possibilities with contractual commitments before signing.
- • Maintain and contribute to shared technical documentation, deployment playbooks, and runbooks that standardize processes and reduce onboarding time for future deployments.
- • Conduct technical discussions directly with customer stakeholders during implementation meetings, translating complex system behaviors into clear, jargon-free explanations without losing technical accuracy.
- • Work remotely as part of a globally distributed team, managing time zone differences while maintaining high responsiveness and ownership over technical outcomes.
- • Continuously refine AI agent configurations based on observed customer interactions, applying practical fluency in LLM behavior to optimize response quality, memory retention, and cross-channel consistency.
- • Collaborate with internal engineering teams to prioritize fixes and feature requests based on field observations, acting as the voice of the customer within product development.
- • Adapt deployment strategies dynamically based on evolving customer infrastructures, ensuring scalability and reliability under varying technical conditions.
- • Contribute to internal knowledge-sharing rituals such as demo days and Slack-based AI workflow discussions to elevate team-wide competency in AI agent deployment and troubleshooting.
- • Maintain high standards of technical rigor while operating at startup speed, balancing thoroughness with urgency to meet critical deployment deadlines.
- • Ensure all deployments align with Siena’s core philosophy: turning every customer interaction into intelligence that makes the next one better.
🎯 Requirements
- • 5+ years in technical implementation, integration engineering, or software engineering with a customer-facing component
- • Strong working knowledge of helpdesk and CX platforms (Zendesk, Gorgias, or similar), including API integrations, webhooks, and automation logic
- • Experience with Shopify, e-commerce platforms, and REST APIs
- • AI-fluency: practical understanding of LLM-powered agents—capable of configuring, testing, and iterating on agent behavior in production
- • Ability to diagnose and resolve technical blockers independently in customer environments without constant escalation
- • Comfort leading technical conversations with customers, explaining complex systems clearly without jargon
🏖️ Benefits
- • Great salary plus opportunity for equity or stock grants
- • Learning budget for professional growth and tool acquisition
- • Premium AI tool subscriptions (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) with quarterly budget for new tools
- • Remote work with a globally distributed team operating at the cutting edge of AI and customer experience
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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