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 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 Deployment Manager, AI Agents, you own the delivery side of the business. You're embedded in customer accounts, managing complex multi-stakeholder deployments from kick-off through to sustained automation performance. You're the person who keeps things moving when complexity is high, timelines are tight, and no two accounts look the same. This isn't a role for order-takers. The deployment team at Siena is the difference between a customer that churns and a customer that expands. You own that outcome. Who you are 5+ years in customer experience operations, support ops, implementation, or CX agency work - deep helpdesk fluency (Zendesk, Gorgias, or similar) is a strong plus You understand how support operations actually work: ticket lifecycle, routing logic, automation health, escalation flows. This is the context that takes years to build and that we can't afford to teach from scratch A natural project manager - you break complex problems into simple plans, keep multiple workstreams on track, and keep every stakeholder aligned without burning out SaaS or e-commerce background is a bonus; CX operations depth is the primary signal You communicate clearly under pressure: written updates, verbal briefings, Slack threads - you make the status of every account visible without anyone having to ask You're proactive with data: you watch automation rate, deflection, and escalation patterns, catch the dip before the customer flags it, and bring evidence when something needs attention - not gut feel. AI fluency - you use AI tools actively in your workflow and can enable and guide, confidently customers who are new to the space You co-lead - you're not here to own everything solo, you're here to share the load with a team and make the whole function stronger Remote What you'll do Own deployments from zero to live - kick-off, automation setup, stakeholder alignment, and hitting the metrics that matter Co-lead strategic accounts with senior team members, taking on responsibility progressively as you ramp Apply your CX ops knowledge to diagnose why accounts are stuck: helpdesk configuration, ticket routing gaps, automation logic, escalation failures - and drive the fix Keep every account you touch moving: daily updates, proactive escalations, clear documentation of progress and blockers Manage customer expectations with confidence: hold timelines, push back when scope creeps, and keep relationships intact when things get hard Shadow and support senior team members for the first 30 days, then take the lead on accounts Feed operational patterns back to the product team: you see problems across accounts before anyone else does 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.