Toronto, Ontario, Canada
Remote only
Siena is the Agent of Record for CX, built for consumer brands like Spanx, FIGS, Brooklinen, and Grüns.
It runs as a connected multi-agent stack on top of a shared intelligence layer: agents that sell, support, listen, handle social and voice across the entire customer journey, turning every conversation into signal you can act on.
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 set the bar rather than follow one, keep reading.
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 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 is the difference between a customer that churns and one that expands, and you own that outcome.
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
The Bar: If you're missing any of these, this isn't the role for you.
5+ years in customer experience operations, support ops, implementation, or CX agency work, with deep helpdesk fluency (Zendesk, Gorgias, or similar)
You understand how support operations actually work: ticket lifecycle, routing logic, automation health, escalation flows
AI fluency: you use AI tools actively in your workflow and can confidently enable and guide customers who are new to the space
Strong Signal: Not dealbreakers, but what separates a good hire from a great one.
A natural project manager: you break complex problems into simple plans and keep every stakeholder aligned without burning out
You communicate clearly under pressure and make the status of every account visible without anyone having to ask
You're proactive with data: you catch the dip before the customer flags it and bring evidence, not gut feel
You co-lead: you're here to share the load with a team and make the whole function stronger
Nice to Have: Bonus, not required.
SaaS or e-commerce background (CX operations depth is still the primary signal)
You wait for tickets to tell you something's wrong instead of watching the data yourself
You want to own everything solo rather than share the load with a team
You need a stable, unchanging account list rather than jumping into whatever's on fire
Real ownership. You will own problems, not tasks, with the autonomy to solve them your way and the trust to do it without a manager in your inbox.
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, not a crowded field to compete in.
A team that respects your judgment. Globally distributed, async-first, low bureaucracy. We hire adults and treat you like one.
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.
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.
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.
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