Senior Deployment Engineer, AI Agents

Siena AI • Toronto, ON

1d • Remote

About The Position

Siena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions. Siena doesn't just automate support; it powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human. We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.

We're a small, distributed team that punches way above our weight. Every person here has outsized impact because we've built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with. If you're excited about building something that doesn't exist yet, keep reading. We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels.

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
• You can read a customer's technical setup, identify what's broken or misconfigured, and drive a fix without needing to escalate every time
• AI-fluency - you understand how LLM-powered agents work in practice, not just in theory; you can configure, test, and iterate on agent behaviour
• You're comfortable in customer meetings when the conversation gets technical - you can explain what you're seeing without jargon and without losing the room
• Shopify, e-commerce platform integrations, and REST APIs are familiar territory

Responsibilities

• Embed with strategic accounts as the technical member of the deployment pod - alongside a Deployment Manager and/or Forward Deployed PM
• Diagnose and resolve technical blockers: integration failures, Zendesk configuration issues, automation logic gaps, data sync problems
• Build account-specific automations and integrations that aren't yet supported out of the box
• Own the technical setup of new accounts during onboarding - integrations live, data flowing, first automations configured
• Surface patterns across accounts to the engineering and product teams: recurring technical issues that should become platform features rather than one-off fixes
• Contribute to shared technical documentation and deployment playbooks that reduce ramp time for every future account
• Participate in technical scoping during late-stage sales - help the team understand what's realistic before contracts are signed

Benefits

• Great salary plus the opportunity for equity or stock grants.
• Learning budget.
• Premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed