Head of Education & Community

Siena AI • $90K — $120K *

Kitchener, ON N2A 1A5In-Person

Education, Government & Non-Profit

Less than 5 years of experience

More than 3 months ago

Job Overview by Ladders

Qualifications

5-7 years in product training and education roles
Deep understanding of AI products and the ability to teach and demo them
Proven experience in building communities and educational programs
Strong storytelling and communication skills
Track record of launching initiatives from concept to execution

Responsibilities

Run educational sessions for product releases to ensure team knowledge retention
Conduct customer workshops focused on specific use cases for impactful outcomes
Design a streamlined customer onboarding process from contract to value realization
Onboard new hires through a structured, productive training program
Develop a comprehensive demo library for varied audiences
Establish Siena Academy with certifications and learning paths for users
Create a community space for ongoing customer and partnership engagement
Educate the broader market with open courses and frameworks
Support sales teams with tailored demo scripts and product narratives
Develop AI systems to enhance educational delivery and scalability

Benefits

Opportunity to significantly impact product development and company direction
Be part of a globally distributed team at the forefront of CX and AI technology
Access to a learning budget for personal and professional growth
Potential for equity or stock grants as part of the compensation package
Join a company where your contributions have a tangible effect
Engage with cutting-edge AI to reshape customer experience

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Full Job Description

The role

Siena is the CX operating system for brands. We ship faster than anyone in the category, and that pace has outrun our ability to teach what we're building. Our team learns about new products in Slack. Our customers learn about them on calls. The market learns about them too late.

This role exists to change that.

You will 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.

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About Siena AI

Siena AI is a developer of an autonomous chat platform that aims to transform the way it runs and interacts with consumers by combining human empathy and intelligent automation. The platform provides capabilities such as product information, order tracking, address changes, returns and product exchanges, subscription and retention management, allowing firms to conduct customer care and social media interactions autonomously.

Siena AI Careers

There has never been a better time to join the global team of Siena AI professionals, a leading force in the artificial intelligence sector.

Work You'll Do

Join Siena AI's market-leading team to assist some of the most innovative companies in mastering their technology-driven transformation journeys. At Siena AI, the fusion of technology, industry expertise, and digital innovation puts the company at the forefront of the AI industry. Lead in a unique market position, harnessing the power of AI to drive industry-wide changes and deliver unparalleled innovation. Engage with a global team of business and technology advisors, helping clients navigate through complex AI integrations and transformations. Collaborate with a dedicated group of AI experts, driving forward the boundaries of what's possible in technology and business.

Introducing the Siena AI Business Group Advisory

This team is dedicated to building a leading advisory service, guiding major companies through their digital transformation journeys using advanced AI solutions.

Innovative Work

Be part of the largest group of AI professionals, delivering targeted solutions through a depth of consulting experience and innovation that is unmatched in the industry.

Innovate and Grow

Deliver solutions that are trusted by enterprises worldwide, leveraging Siena AI's extensive consulting experience and innovative approaches.

Be Part of a Great Team

Join a team that works on cutting-edge Microsoft technology and harnesses the capabilities of a global scale operation to develop joint solutions.

Future-Proof Your Career

With Siena AI, go as far as ambition can take, with endless opportunities to advance careers through unmatched training, development, and certification support.

Explore Job Opportunities

Discover how Siena AI is moving industries towards more predictive and efficient practices with advanced AI solutions. From improving operational efficiencies to pioneering new industry standards, the impact is profound and rewarding.

The Siena AI Leadership and Innovation

With a commitment to leadership in AI and a culture that fosters diversity and professional growth, Siena AI is a beacon of innovation. The company's global scale and joint solution development enable clients to overcome challenges and lead transformations in their fields.

Stay Connected

Join the Team

Search for open positions that match skills and interests. Siena AI looks for passionate, curious, creative, and solution-driven team players.

SEARCH SIENA AI JOBS

Keep Up to Date

Stay ahead with career tips, insider perspectives, and industry-leading insights that can be put to use today—all from the people who work at Siena AI.

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Learn more about Siena AI

Size

11 employees

Industry

Information Technology

* Ladders Estimates

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