Location Toronto; Buenos Aires; Kitchener-Waterloo; Mexico City; Montreal; Pheonix; Rio de Janeiro; Salt Lake City; Sao Paolo Employment Type Full time Location Type Remote Department Deployment Deadline to Apply June 14, 2026 at 11:00 AM EDT Meet Siena 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. The team 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. The role As a Senior Deployment Engineer, AI Agents, you're the technical layer inside our deployment pods. You're embedded with accounts where the complexity goes beyond what a generalist deployment manager can unblock alone - integration failures, automation logic that won't behave, helpdesk configurations that need an engineer's eye. You're not a pure customer-facing role and you're not a pure internal engineering role. You're the bridge. You're energised by hard technical problems inside a customer context - and you know that fixing one well scales to ten accounts. Who you are 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 Remote What you'll do 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 Why Siena? Meaningful impact. Your work directly shapes our product and company. Globally distributed team working at the bleeding edge of CX and AI. Great salary plus the opportunity for equity or stock grants. Learning budget. If you're growing, so are we. The thrill of building something new. Join us at a stage where your contributions matter most. AI-fluency. Make AI your second nature. Tackle unsolved problems. We’re redefining how customer experience will look like in the next decades. Our values The people who thrive here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain later. They're direct about feedback—both giving and receiving it—because they care more about getting things right than being polite. They maintain high standards while moving at startup speed, and they build real relationships with teammates because they know that's how great work gets done. When things get tough, they adapt and keep pushing forward. Our approach to AI The people who thrive here treat AI like a natural extension of themselves. They've built their own ecosystem of agents - some for research, others for debugging, writing, analysis, or writing code. They know which AI works best for what problem. Everyone gets premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools. But the magic happens in how we share knowledge. Demo days where someone shows off a clever workflows. Slack threads about which model handles a specific use case better. Learning from each other's AI workflows. At Siena, we’re not just looking for people who can do a job. We’re looking for people who want to break boundaries, create the future, and reshape industries. If that’s you, we look forward to your application. We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at talent@siena.cx. Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.