Head of Education & Community - Siena

Meet Siena

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.

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.

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

• Product Education: 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.
• Workshops & Sessions: Run customer workshops and recurring product sessions. One use case at a time. Real depth, real outcomes.
• Onboarding Paths: Build the customer onboarding path from signed contract to first value, repeatable across every segment. Onboard every new hire to ensure they ramp quickly and productively.
• Demo Library: Build a live, recorded, vertical-specific, and persona-specific demo library for sales and customers.
• Siena Academy: Build curriculum, certifications, and learning paths (internal and external) to establish the credential brands earn to show they know Siena.
• Community Building: Build the Siena community, creating recurring spaces, events, and rituals where customers, partners, and operators connect and learn.
• Market Education: Educate the market through open courses, public content, and frameworks, turning the Academy into the category-defining resource on CX AI.
• Sales Enablement: Arm sales with demos, narratives, product positioning, demo scripts, and vertical storylines.
• AI Systems: Build the AI systems that scale all of the above. Teach the agents how to teach.

What We're Looking For

• Product-fluent: You understand AI products deeply. You can use Siena, break it, and teach it.
• Exceptional Teacher: You make complex things simple, turning a use case into a clear, actionable 30-minute session.
• Storyteller & Communicator: You write, present, and translate complex product features into clear narratives.
• Community Builder: You have experience gathering people around a shared interest and creating engaging spaces.
• AI-native: You build agents and systems, replacing workflows with AI naturally.
• Builder: You have shipped a curriculum, program, academy, or community from zero without a brief.
• Excited about Consumer Brands: Passionate about serving brands like Spanx, Allbirds, FIGS, HexClad, Brooklinen, Coterie, Grüns, and Kitsch.

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: Own problems, not tasks, with the autonomy to solve them your way.
• Work that Ships and Matters: Reach real consumer brands fast.
• Category Creation: Work on the Agent of Record, a new ground with unsolved problems and cutting-edge models.
• Adult Environment: Globally distributed, async-first, low bureaucracy.
• Compensation: Great salary plus equity or stock grants.
• Learning Budget: Dedicated budget to support your growth.
• AI-fluency by Default: Push your work with production AI further and faster.