AI Enablement Specialist

Your Epic Quest as Our AI Enablement Specialist

AI operations here means hands-on AI support and enablement: helping everyone at the company do better work with AI. Most days a teammate brings a problem that’s tangled, half explained, and urgent. The job is to get on a call, figure out what’s really going on, and leave them with something simple that works. Then it becomes a skill, a doc, or a tool so nobody has to ask twice.

This is a support and enablement role at its core - if you enjoy helping people and you’re highly capable with tools like Claude Code, keep reading. If you mainly want to build product with minimal interaction, this probably isn’t the right fit.

We define the problem before we automate it: an agent can’t solve something no human has figured out and clearly described first. That takes a clear view of what AI can’t do, real taste for building the smallest thing that solves the problem, the discipline to verify model output before passing it along, and the discretion to flag anything that could become a compliance or security issue - we work in healthcare.

How Penguins Think About Ai:

We define the problem before we automate it. An agent cannot solve something that no human has figured out and clearly described first.

We don't throw agents at a problem to see what sticks. Sometimes the right answer is a well built skill or a multi-tool workflow. Sometimes it is a checklist, a cleaner handoff, or one new field in HubSpot. I need someone who can tell the difference, and who will say so.

That takes four things:

• A clear view of what AI can't do. You know where models fail, where they quietly make things up, and when a human has to stay in the loop
• Taste. You build the smallest thing that solves the real problem, and it is pleasant to use
• Real understanding. You can explain anything you build, ship, or teach. You verify model output before you pass it along, and you are comfortable saying "I don't know yet."
• Discretion. We work in healthcare. You notice when something could become a compliance or security issue and you raise it early

Your Day-to-Day Superpowers: What You’ll Actually Do:

• 1-on-1 enablement: Get on calls with teammates across sales, ops, engineering, and leadership. Learn their workflow, show them a better way, make it stick
• Live troubleshooting: Debug Claude Code, Claude Desktop, skills, and MCP connections in real time, often over screen share. Stay calm, think out loud, get them unblocked
• Build skills and workflows: Turn recurring requests into reusable skills, prompts, and workflows that chain several MCPs and services together (HubSpot, Microsoft 365, Google Workspace, Slack, Notion, and more)
• Curate the company context repo: Keep our shared context, prompts, and templates accurate, organized, and worth using
• Spot the real bottleneck: When a request is really a process problem dressed up as an AI problem, recognize it and bring it to Nick
• Teach: Write the short guide, record the two-minute walkthrough, run the occasional session
• Stay at the frontier: Try new models, harnesses, and tools as they land, then talk through their limitations and potential opportunities

Strategy, policy, architecture, and the risky or sensitive work can stay with me. You will learn all of it over time, with support along the way.

What Success Looks Like In Your First 90 Days!

• Teammates come to you directly for AI help, and they leave unblocked
• You own day to day AI tech support end to end
• You have shipped several skills or workflows that people actually use
• The company context repo is cleaner and more useful than when you started

What We're Looking For: Your AI Enablement Arsenal!

• Clear, professional communication: You’re a fluent communicator, written and live, with engineers, executives, and people who’ve never opened a terminal - these matters more than anything else on this list
• Live problem-solving: You’ve done remote tech support, consulting, or something like it, and a messy problem on a screen share doesn’t rattle you
• Real AI fluency: You already use Claude Code, Claude Desktop, skills, and MCP for real work or for fun, and you’ve connected MCP servers and fixed them when they broke
• Prompt and context engineering: You understand why an output is bad and how to fix the inputs
• Microsoft 365 and Google Workspace: You’re fluent in both as a power user and light admin
• Git and the command line: You use git daily and are comfortable working from the terminal
• Fast, independent learning: You teach yourself and pick up new tools from docs and experimentation, often on your own time because you want to

Bonus Points: Your Secret Weapons!

• You've not just survived but thrived in the beautiful chaos of a high-growth startup

Nice to have skills:

• Python or JavaScript/TypeScript, or full stack development exposure
• Docker, and AWS, Azure, or GCP
• HubSpot
• Open source agent harnesses, or you have built your own harness or MCP server
• Healthcare experience, or exposure to HIPAA, SOC 2, or similar compliance work
• Formal training in software development or IT. Helpful, never required.

The Culture Fit: Join Our Colony!

You'll waddle with us if:

• You like your coffee with a side of delightful chaos
• You're fuelled by complexity and obsessed with delivering amazing results
• You want to deliver something that fundamentally matters, transforms healthcare and ultimately saves lives

Education & Qualifications: Brainiac Basics

• High school diploma or Associate Degree

Comp & Perks: Because Even Superheroes Need Support!

• Competitive salary: We reward greatness!
• Medical, vision, and dental coverage: Keep you healthy and smiling
• Generous vacation policy and company holidays: Recharge and conquer!
• A front-row seat in one of healthcare's most exciting AI companies – witness history in the making