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.
The role
As a Forward Deployed Product Manager, Agents, you're embedded directly with strategic accounts, owning their deployment outcomes end-to-end while feeding the insights back into the platform. You're the person on the ground who deploys agents, drives automation rates, and turns what you learn into product improvements that scale across every customer.
You're energised by the loop: deploy agents → drive outcomes → identify gaps → build platform improvements → repeat.
Who you are
5+ years in PM, solutions engineering, forward deployment, or technical account ownership
AI-native mindset - you live in Claude, Cursor, and build your own workflows before anyone asks
You can scope webhooks, OAuth flows, and complex integrations without needing an engineer to translate
You've lived the problems customers are trying to solve - you know what great CX looks like from the inside
You can diagnose whether a deployment problem is technical, operational, or stakeholder-driven, and prioritise accordingly
You're comfortable advising CX leaders on organisational design, process optimisation, and transformation strategy
You ship features, write docs, run demos, and measure what matters
Remote - Canada, Latin America preferred
What you'll do
Own AI agent outcomes for strategic accounts end-to-end - automation rates, resolution rates, time-to-value
Deploy agents, identify what's blocking progress, then build the platform fix so the next account benefits
Work directly with enterprise CX leaders to design AI transformation roadmaps - and execute them
Turn deployment insights into platform capabilities. What you learn in the field shapes what we build next
Build and improve agent capabilities that work across platforms - support, shopping, reviews, voice, social
Design evaluation systems: QA suites, automated testing, performance monitoring
Run full launch cycles from internal testing to GA, including customer enablement
Demo your own products and co-sell alongside sales - you'll be known by name in our customer communities
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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