Head of Product Education & Community

Location Type: Remote Location: Toronto; Kitchener-Waterloo; Montreal; Austin; Remote - Europe; New York; Atlanta; Chicago Employment Type: FullTime Department: GTM 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. If you want to set the bar rather than follow one, keep reading. THE ROLE You're a product person who teaches: you'll build the curriculum, community, and credentials that make Siena something people learn, not something they discover. You'll teach three audiences: the team who builds it, the customers who use it, and the market that will eventually adopt it. 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, for real depth and real outcomes - Build the customer onboarding path, from signed contract to first value, repeatable across every segment - Onboard every new hire so they ramp through your program and get productive faster because of it - Build the demo library (live, recorded, vertical and persona-specific) that Sales pulls from and customers learn from - Build Siena Academy: curriculum, certifications, and 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 through open courses and public content that others adopt, making the Academy the category-defining resource on CX AI - Arm sales with demos, narratives, and positioning that close deals - Build the AI systems that scale all of the above. You teach the agents how to teach WHO YOU ARE The Bar: If you're missing any of these, this isn't the role for you. - Product-fluent. You can demo, break, and teach Siena at depth - An exceptional teacher and storyteller. You've turned complex products into teachable, memorable skills before - A builder. You've shipped something from zero (product videos, a curriculum, a program, an academy, a community) without a brief Strong Signal: Not dealbreakers, but what separates a good hire from a great one. - You understand AI products deeply and use Siena, break it, and teach it - You're AI-native: you build agents and systems, and you've replaced workflows with AI before you joined us - You've gathered people around something they care about and know how to create spaces they want to show up and stay in Nice to Have: Bonus, not required. - Experience building education or community functions inside a fast-growing B2B or consumer tech company - Experience in eCommerce NOT A FIT IF: - You want a content team underneath you to produce output. This is a team of one to start - Your background is L&D or corporate training with no product depth - You treat education as separate from revenue rather than something that moves win rate and retention 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. 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. HOW WE HIRE 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.