Head of Education & Community

Meet Siena. Siena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions. Siena doesn't just automate support; it powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human. We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.

The team is a small, distributed group that punches way above our weight. Every person here has outsized impact because we've built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with.

If you're excited about building something that doesn't exist yet, keep reading. We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels.

The role exists to 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:

• 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 they're 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 we're 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. You've 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. You've replaced workflows with AI before you joined us, and you'll do it again here.
• A builder. You've 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:

• Product-fluent. Can demo, break, and teach Siena at depth.
• Exceptional teacher and storyteller. Has turned complex products into teachable, memorable skills before.
• AI-native. Builds with AI, not just uses it.
• Builder. Has shipped something from zero.

Why Siena?

• Meaningful impact. Your work directly shapes our product and company.
• Globally distributed team working at the bleeding edge of CX and AI.
• Great salary plus the opportunity for equity or stock grants.
• Learning budget. If you're growing, so are we.
• The thrill of building something new. Join us at a stage where your contributions matter most.
• AI-fluency. Make AI your second nature. Tackle unsolved problems. We’re redefining how customer experience will look like in the next decades.

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 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.

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.