Deployment Manager (AI Agents)

Join Siena as a Deployment Manager, where you'll be responsible for managing complex multi-stakeholder deployments from kick-off to sustained automation performance. You'll work closely with customer accounts, applying your CX ops knowledge to diagnose and drive fixes for any issues that arise. This role requires strong project management skills, deep helpdesk fluency, and a proactive approach to data. Enjoy the flexibility of remote work, unlimited PTO, and stock options.

• Own deployments from zero to live, managing complex multi-stakeholder deployments from kick-off through to sustained automation performance.
• Co-lead strategic accounts with senior team members, taking on responsibility progressively as you ramp, and apply your CX ops knowledge to diagnose and drive fixes.
• Keep every account you touch moving by providing daily updates, proactive escalations, and clear documentation of progress and blockers.
• 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
• 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
• Remote
• SaaS or e-commerce background is a bonus; CX operations depth is the primary signal
• 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
• A natural project manager - you break complex problems into simple plans, keep multiple workstreams on track, and keep every stakeholder aligned without burning out
• 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 communicate clearly under pressure: written updates, verbal briefings, Slack threads - you make the status of every account visible without anyone having to ask
• AI fluency - you use AI tools actively in your workflow and can enable and guide, confidently customers who are new to the space
• 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