The roleYou are, first, a product expert. You can take a complex, fast-moving product and dissect it into something people understand - across whatever format the moment needs: a demo, a workshop, a doc, a short video, 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 waiting for you, and no content team underneath you-you make the thing.
This isn't 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 in the product, build with AI, and have shipped something real from zero.
What you'll own- Product fluency, made teachable. You go deep on the product, then turn that depth into content people actually retain-across formats, for both customers and the internal team. This is the root of everything else in the role.
- 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 you own demo quality and demo-to-close conversion as outcomes, not activities.
- Siena Academy. The curriculum, certifications, workshops, and learning paths-public and private. The goal is for it to become 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. Today it's events and one-off moments. You 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- You 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 3 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 areThese are non-negotiable:
- Product-fluent, first and foremost. You can demo, break, and teach a product at depth. Not a marketer who skimmed the product-someone who lives in it and gets energy from understanding how it actually works.
- A translator. You take complex features and turn them into things people understand and salespeople can sell. Different formats, different audiences, same clarity.
- An exceptional teacher and storyteller. You have a track record of turning complex products into skills people actually 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, a function. Improving an inherited system isn't the same thing.
- 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 (or Fin), Attentive, Klaviyo, 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 scaled a customer community from zero. Built one, not 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's comfortable 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 valuesThe 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 AIThe 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.
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 [redacted].
