Head of Education & Community

Siena · Toronto · FullTime

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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

Siena is the CX operating system for brands. We ship faster than anyone in the category, and that pace has outrun our ability to teach what we're building. Our team learns about new products in Slack. Our customers learn about them on calls. The market learns about them too late.

This role exists to change that.

You will teach Siena to three audiences: the people who build it, the brands who use it, and the market that will eventually adopt it. You will build the curriculum, the community, and the credentials that make Siena something people learn, not something they discover.

You are a product person who teaches. A builder who writes. A communicator who ships.

What you'll do

What we're looking for

Hard filters

  1. Product-fluent. Can demo, break, and teach Siena at depth.

  2. Exceptional teacher and storyteller. Has turned complex products into teachable, memorable skills before.

  3. AI-native. Builds with AI, not just uses it.

  4. Builder. Has shipped something from zero.

Why Siena?

Our values

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.


Our approach to AI

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 [email protected].

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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