Head of Product Education & Community
Siena AI · Remote · Toronto · New York ·
COMPENSATION
€•• – ••k
Listed on the employer's job board (Ashby)
- Fully remote global team
- Build function from zero
- AI-native culture
- Equity or stock grants
- Senior leadership role
You will define how users learn and engage with Siena, an AI agent stack for consumer brands. The role requires building the entire education function from scratch, including onboarding paths, demo libraries, and the Siena Academy. You will teach three distinct audiences: the internal product team, current customers, and the wider market adopting CX AI.
This is a high-autonomy position for a builder who prefers direct communication and async work. You will create repeatable processes for customer success and sales enablement, ensuring every release is accompanied by clear documentation and training. The goal is to make Siena a category-defining resource through open courses and community rituals.
What you'll do
- Lead product education for internal teams with demos and docs for every release
- Conduct customer workshops focused on specific use cases and outcomes
- Design the customer onboarding journey from contract signing to first value
- Create onboarding programs to accelerate new hire productivity
- Build a library of live and recorded demos for sales and customer self-service
- Establish Siena Academy with curriculum, certifications, and learning paths
- Foster a community space for customers, partners, and operators to connect
- Produce public content and open courses to educate the broader market
- Provide sales teams with narratives and positioning materials to close deals
- Develop AI systems that automate and scale educational delivery
What you'll need
- Deep product fluency with ability to demo and teach complex tools
- Proven track record as an exceptional teacher and storyteller
- Experience building education programs, academies, or communities from scratch
- Ability to work autonomously without a supporting content team initially
- Strong product depth beyond general corporate training or L&D backgrounds
- Focus on linking education directly to revenue win rates and retention
Nice to have
- Deep understanding of AI products and experience using Siena
- AI-native mindset with experience building agents or replacing workflows with AI
- Skill in creating engaging spaces that retain community members
- Background in education or community roles within B2B or consumer tech
- Prior experience in the eCommerce sector
Stack
- Siena
- ChatGPT
- Claude
- Perplexity Pro
- Cursor
- Lovable
How you'll work
- Fully distributed global team
- Async-first communication style
- Defaults to writing over meetings
- High autonomy with low bureaucracy
- Team of one for this function initially
What you get
- Competitive salary plus equity or stock grants
- Learning budget for professional growth
- Premium accounts for major AI tools provided
- Quarterly budget for exploring new AI tools
- Real ownership of problems and solutions
Hiring process
- AI-assisted screening tools used initially
- All final hiring decisions made by humans
- Option to request human-only review available