Deployment Manager, AI Agents

Role Description

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.

Qualifications

• 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
• 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're proactive with data: you watch automation rate, deflection, and escalation patterns
• AI fluency - you use AI tools actively in your workflow and can enable and guide 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

Requirements

• 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

Benefits

• Real ownership - you will own problems, not tasks, with the autonomy to solve them your way
• Work that ships and matters - what you build reaches real consumer brands fast
• A category we are creating - the Agent of Record is new ground, with unsolved problems and cutting-edge models
• A team that respects your judgment - globally distributed, async-first, low bureaucracy
• Great salary plus equity or stock grants - own a piece of what you build
• Learning budget - if you are growing, so are we
• AI-fluency by default - few places will push your work with production AI further or faster

Company Description

Siena is the Agent of Record for consumer brands, managing the entire customer journey on a shared intelligence layer. Hundreds of brands already run real customer volume on Siena in production, and we are racing to build what comes next.