Head of Education & Community

Department: GTM

Location: Toronto, Kitchener-Waterloo, Montreal, Austin, Remote - Europe, New York, Atlanta, Chicago

Employment Type: FullTime

Meet Siena

Siena is the 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.

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 set the bar rather than follow one, 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 were 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 youll do

• Run product education for the Siena team. Every release lands with a session, a doc, and a demo that the company actually walks away knowing.

• Run customer workshops and recurring product sessions. One use case at a time. Real depth, real outcomes.

• Build the customer onboarding path. From signed contract to first value, repeatable across every segment.

• Onboard every new hire. They ramp through your program, and theyre productive faster because of it.

• Build the demo library. Live, recorded, vertical-specific, persona-specific. Sales pulls from it. Customers learn from it.

• Build Siena Academy. Curriculum, certifications, learning paths. Internal and external. The credential brands earn to show they know Siena.

• Build the Siena community. The recurring spaces, events, and rituals where customers, partners, and operators come to learn from us and each other.

• Educate the market. Open courses, public content, frameworks others adopt. The Academy becomes the category-defining resource on CX AI.

• Arm sales with demos, narratives, and product positioning. Demo scripts, vertical storylines, the words that close deals.

• Build the AI systems that scale all of the above. You teach the agents how to teach. Your taste is the final filter.

What were looking for

• Product-fluent. You understand AI products deeply. You can use Siena, break it, and teach it.

• An exceptional teacher. You make complex things simple. You take a use case and turn it into a 30-minute session that someone walks away knowing.

• A storyteller and communicator. You write, present, and translate complex product into clear narrative. Every workshop, every certification, every piece of content is a story.

• A community builder. Youve gathered people around something they care about. You know how to create the spaces where customers, partners, and operators want to show up and stay.

• AI-native. You build agents. You build systems. Youve replaced workflows with AI before you joined us, and youll do it again here.

• A builder. Youve shipped something from zero. A curriculum, a program, an academy, a community. You operate without a brief.

• Excited about consumer brands. We serve Spanx, Allbirds, FIGS, HexClad, Brooklinen, Coterie, Grüns, Kitsch, and dozens of others.

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?

• 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.

Our values

The people who thrive here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain later. Theyre 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 thats 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. Theyve 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 others 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.