Product Education & Community Lead

Siena AI; Boston (KY); On-site; USD 70,000 - 90,000; Full time

Benefits offered by this job

Great salary with equity options

Learning budget

Globally distributed team

Job summary

Siena AI in Boston, Kentucky seeks a Product Expert to translate complex AI product features into accessible content. This role involves building training materials, enhancing sales enablement strategies, and fostering a strong community. You’ll become integral to product education and be pivotal in creating resources that help both the team and customers understand and utilize the product effectively.

Applicants should have a deep understanding of AI and proven experience in product education and community building.

Qualifications

• Ability to translate complex product features into understandable content.
• Exceptional skills in demoing and teaching product intricacies.
• Experience building communities or educational resources.

Responsibilities

• Own product training and education for the internal team.
• Develop sales enablement materials and demo quality.
• Create and maintain Siena Academy curriculum and workshops.

Skills

Product fluency

Teaching and storytelling

Sales enablement

AI knowledge

Community building

Job description

Meet Siena is the first intelligence layer for customer experience. We are building 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

We’re a small, distributed team 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 more fun to work with.

The role

You are, first, a product expert. You can take a complex, fast‑moving product and break it down into something people understand—whether it’s a demo, a workshop, a doc, a short video, or a certification path. Second, you know how to turn that understanding into something that sells. You break features into sellable units, and you teach the team how to put them in front of a customer. Third, you build the community that turns all of that into a network that compounds. It’s a founding role: a blank page, a fast product, and real ownership over the result. No playbook or content team under you—you make the thing. It is not a fit if you’ve spent your career running someone else’s training program inside a big org; it is a fit if you live the product, have built with AI, and have shipped something real from zero.

What you’ll own

• Product fluency, made teachable. You go deep on the product and turn that depth into content people retain—across formats for customers and the internal team.
• Sales enablement. Demos, talk tracks, the demo library, objection handling, vertical‑specific demos, and the positioning sales uses to close. You translate product depth into sellable units and own demo quality and demo‑to‑close conversion as outcomes.
• Siena Academy. The curriculum, certifications, workshops, and learning paths—public and private—becoming the resource people in CX AI point to.
• Customer onboarding. The path from contract signed to first value: documented, repeatable, and shorter than it is today across every segment.
• Internal team education. Every new hire ramps through your program. Every product release becomes a learning moment within 48 hours of ship, not a Slack post that scrolls away.
• Community. AI Labs, Siena Renaissance, founder voices, the customer council. Build the system that turns customers and prospects into a flywheel.
• AI agents that scale you. You teach the agents how to teach; your taste is the final filter on what ships.

Out of scope: demand gen, paid, brand, category narrative, PR, and product launches as market moments. Growth owns those. You make the team and the customers great at the product.

What success looks like in 90 days

• Know the product cold and the team knows it because of you. Every new hire ramps through your program, and every release lands as a learning moment inside 48 hours of ship.
• Demos are sharper and demo‑to‑close is measurably up. Battle cards, objection handling, and vertical demo scripts shipped for the top three verticals.
• Siena Academy v2 is live. Core curriculum shipped, with the first cohort of customers and team members through it.
• Onboarding from signed to first value is documented, repeatable, and measurably shorter than today.
• One‑to‑many product workshops run weekly—activating customers, teaching them to use the platform properly, and expanding them into new use cases and SKUs.

Who you are

• Product‑fluent, first and foremost. You can demo, break, and teach a product at depth.
• A translator. You take complex features and turn them into things people understand and salespeople can sell.
• An exceptional teacher and storyteller. You have a track record of turning complex products into skills people retain.
• AI‑native. You build with AI. You’ve shipped agents and workflows that replaced real manual work, not just used the tools.
• A builder. You’ve shipped something from zero—an academy, a curriculum, a community, or a function.
• An operator. Team of one to start, no agency dependency. You make the work; you don’t manage people who make it.

Nice to have

• You’ve done this at Intercom, Gorgias, Recharge, Shopify, Gainsight, Notion, Figma, or Linear—companies that built education and community into competitive moats.
• You’re doing this exact job at another AI company today.
• You’ve built a customer community from zero, not just managed one.
• You’ve built product or sales enablement that measurably moved win rate.

This is not the role for you if

• You’re a generalist trainer who is comfortable at a layer above the product. This role lives inside it.
• Your background is L&D or corporate training only.
• You’ve managed a community but never built a compounding system. A Slack group isn’t a flywheel.
• You need a content team underneath you to produce output.
• You treat education as separate from revenue. If you can’t tie your work to win rate, retention, and expansion, we’re not a fit.

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 are direct about feedback—both giving and receiving—it’s about getting things right rather than being polite. They maintain high standards while moving at startup speed and 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 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. The magic happens in how we share knowledge—demo days where someone shows off clever workflows, Slack threads about which model handles a use‑case better, and learning from each other’s AI workflows.

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.