Deployment Manager, AI Agents
Siena
| Company | Siena |
| Category | Data & Analytics |
| Location | Unite States / Canada |
| Remote | Remote |
| Employment | Not stated |
| Level | Manager |
| Salary | Not stated by the employer |
| Posted | 20 Jul 2026 |
| Last verified | 31 Jul 2026 |
| Source | Employer career page (ashby) |
Description
MEET SIENA
Siena is the Agent of Record for consumer brands. One agent that owns the entire customer journey, running on a shared intelligence layer no point tool can replicate.
Consumer brands run ten or more disconnected tools to manage their customers. We collapse that stack into a single agent. It started with support, the hardest surface a brand has, and it expands from there: Shopping Agent, Social Agent, Siena working alongside a brand's own operators. One agent across every surface, with shared memory, shared context, and shared tools.
Hundreds of brands already run real customer volume on Siena in production. This is built, working, and growing, and we are racing to build what comes next.
THE TEAM
We are a small, fully distributed, global team. We have built leverage into how we work, which is what lets a team this size move at the speed we do.
We hire athletes. Everyone here owns real outcomes, defaults to writing over meetings, communicates with directness, and acts the moment they see something worth acting on. Low ego, high standards, fast clock.
If you want to own real problems rather than close tickets, keep reading.
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?
- Real ownership. You will own problems, not tasks, with the autonomy to solve them yo