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 Technical Account Manager, AI Agent Deployment, you own both the technical and commercial health of your accounts. You master how Siena works under the hood to diagnose problems and drive outcomes - and you're commercially sharp enough to turn those outcomes into retention and growth. You're not a pure CSM and you're not a support escalation point. You're the person customers trust to own their results, and who turns that trust into a longer, larger relationship. Who you are 5+ years in technical account management, customer success engineering, or a hybrid technical/commercial role - SaaS, CX platforms, or e-commerce strongly preferred Technically fluent: you understand how integrations work, can read a configuration, and can diagnose common deployment issues without escalating every time You lead with outcomes - automation rates, resolution rates, and whether the account is actually working Commercially aware: you understand ARR, renewal risk, and expansion signals, and can position additional value without it feeling like a pitch AI fluency - you use AI tools actively in your workflow and can enable and guide, confidently customers who are new to the space You're proactive with data: you know what the numbers mean and you act on them before customers ask You build relationships that outlast onboarding - customers want more access to you, not less Remote What you'll do Own technical account health: diagnose automation performance issues, configure improvements, and drive resolution rates without always pulling in engineering Be the primary point of contact for your accounts - customers know you by name and trust that you'll bring them clarity. Run regular business reviews with customer stakeholders - bring data, tell the story, and drive clear next steps Partner with the deployment team during onboarding to ensure the handoff is clean and the account is set up to succeed Translate what you hear from customers into structured product feedback the team can act on 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.