Deployment Manager, AI Agents

Siena AI • Toronto, ON

1d • Remote

About The Position

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. 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.

Requirements

• 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
• Communicate clearly under pressure: written updates, verbal briefings, Slack threads - you make the status of every account visible without anyone having to ask
• 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

Nice To Haves

• SaaS or e-commerce background is a bonus

Responsibilities

• 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

• Great salary plus the opportunity for equity or stock grants.
• Learning budget.
• Premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed