AI Learning Facilitator at Clarinet

About the role

You'll spend the majority of your time facilitating high-energy, hands-on workshops for SMBs and scale-ups. Sessions are dynamic, demo-heavy, and designed to read and respond to the room.

We move fast. Content is updated constantly to keep pace with model releases and what we're learning from clients, sometimes within the same week. New workshops show up on the roadmap with weeks of lead time, not months. The right person finds that energizing rather than disorienting.

When not facilitating, you'll be staying current on AI, learning new content as it ships and contributing back to it from what you see in the room, supporting client relationships, improving how we work, and helping with marketing and external presence.

This role is for you if

• You have a deep understanding of the tools and the underlying mindsets and habits people need to actually change how they work. You bring real grounding in behavioral science and the psychology of change — you don't just know how to set up an automation, you can tell which automations will help and which are just creating new problems to replace old ones.
• You're deeply curious about AI and consider staying current part of the job. You can hold a confident point of view on this week's model releases without needing a research team to brief you.
• You thrive in ambiguity. You're comfortable being told "we're standing this workshop up by next week, here's the outline, report back on how it goes" — and you can shape it as you teach it.
• You model learning agility, not just expertise. You're willing to show your messy first prompt before the polished one, and audit your own AI use live.
• You hold the bar for your own work and bring sharp ideas to others'. You take feedback and apply it on the next session. When your idea doesn't land, you get curious.

What you'll do

• Lead adaptive, hands-on workshops. Most are 90 minutes and virtual. Everyone teaches our core Fluency series; beyond that, you'll grow into other parts of the catalog — AI leadership, tool-specific deep dives, engineering audiences, and new offerings as they ship — based on client demand and your own expertise. There will also be opportunities to teach live and travel.
• Teach the human side of AI adoption, not just the tool. Whether the room is a leadership team, a product org, or a cross-functional cohort, what people actually need is help with the mindset and behavioral shifts — psychological safety, sense-making, identifying which workflows are worth automating in the first place. The buttons-to-click part is the easy half.
• Build and maintain real fluency across platforms. You're hands-on in Claude (including Projects, Skills, and Cowork), Gemini (including Gems and Flows), and ChatGPT. You can demo confidently in any of them and translate between them when a client asks "what's the equivalent of X in Y?"
• Pick up new content quickly. Content is moving. The floor is rising. Last quarter's "advanced" is this quarter's "table stakes." You'll be expected to learn and deliver workshops on tight timelines, sometimes with a draft deck and a recording to watch.
• Represent Clarinet well to clients. You'll have meaningful interaction with client sponsors before, during, and after sessions. They should walk away from every touchpoint feeling informed, in good hands, and confident they made the right call bringing us in. As a key part of this relationship, you will identify and be prepared to recommend future programs that align with their goals.
• Contribute to the product. Surface what's clunky, what's landing, what participants keep getting hung up on. Bring back better examples, sharper framings, new exercises that worked. Our best content has been shaped by facilitators noticing things in the room.

Key competencies

• Adaptive facilitation. You can run a session that landed yesterday and tell tomorrow's group when something needs to be cut, swapped, or expanded. You have a deep bench of moves for low engagement, mixed-skill rooms, curveball questions, and runaway tangents.
• Behavioral and psychological grounding. You understand why adoption stalls, why smart people resist useful tools, and how to design experiences that move people through that resistance. You can articulate this — it's not just intuition.
• Practitioner mindset. You use AI daily for your own work and have built things — agents, workflows, automations — that you actually rely on. You can speak to specific decisions you made and trade-offs you encountered.
• AI depth and strategic breadth. You're a deep user, not just a frequent one. You push past basic tasks like summarizing to use Claude, Gemini, and ChatGPT strategically to alter workflows. You understand the underlying logic of AI, allowing you to instantly map that depth to any new platform.
• Translation. You can take a complicated concept and make it land for a non-technical audience without making it cute or condescending. You can match your language to the audience — CFO, end user, skeptical engineer — without resetting your whole frame.
• SMB and scale-up context. You understand companies where processes are broken, data is siloed, and everyone is in reactive mode. You have worked with SMBs enough to understand the roles and goals of different departments. You can match your pace and language to that reality.

Requirements

• Time zone and hours: US-based, available within 9am–6pm ET.
• Minimum 5 years of work experience (10+ years preferred). Candidates must have direct experience working in or around mid-market startups and scale-ups (~200–5,000 employees) so they fundamentally understand organizational dynamics.
• AI capability: You use AI daily in your own work, at least at the level of someone who's comfortable with agents, custom GPTs/Gems/Projects, automation tools (Zapier, Google Flows, n8n), and emerging interfaces like MCP and Claude Skills. As AI evolves, your skills evolve with it — what counts as "fluent" today won't be the bar in six months, and you find that energizing.
• Facilitation reps in fast-moving environments: Substantial experience facilitating workshops for startups, scale-ups, or SMBs — environments where content shifts, audiences vary, and you're expected to adapt live.
• You thrive here: Long lead times and a stable curriculum bore you. You see ambiguity as room to make something good rather than a sign that something's broken, and learning a new workshop on a tight timeline reads as a fun challenge rather than a fire drill.

Why this role

• Be one of the first full-time facilitators at a company that's positioned to win in AI enablement. Early also means lots of opportunities for growth.
• Work directly with the founding team. Real ownership and real input on what we build next.
• Get deep, hands-on exposure to the AI space — not just keeping current, but in many cases helping shape what "current" means for our clients.
• Join a small, collaborative, remote-first team that takes the work seriously and the rest of life lightly.
• Healthcare stipend and flexible PTO system.