Head of AI Education at Stack
AI is rapidly redefining the economics of freelance and consulting work. Expectations are higher — but so is the leverage available to solo operators who adapt. Stack gives them the systems, skills, mentorship, and tools to turn that leverage into a durable, profitable business, all in one place. Stack is an application-only platform built for serious operators focused on speed, execution, service, and building personal leverage. We’re venture-backed and growing fast!
Content powers the entire Stack flywheel, from learning and outcomes for members to growth and revenue for the business.
We’re hiring a Head of AI Education t own that work. This role spans education, product, brand, community, and growth — and calls for someone with a wide-ranging, AI-fluent skillset.
You’ll be responsible for what we create, how we create it, where it shows up, how it performs, and how it evolves over time.
The scope is broad by design. It requires high agency, a strong point of view, and comfort moving between setting direction and doing the work. In return, it comes with real ownership, freedom to operate, and a seat at the table as the company grows.
• Business playbooks: Maintain and improve the core guides members follow to go from zero to one — from shaping an offer to closing clients and everything in between
• AI tutorials: Plan, produce, and publish practical tutorials that show how to use AI tools and workflows in real worlds scenarios
• Weekly member content: Publish regular updates that help members stay current and focused as the AI landscape changes (tools directories, news updates, prompt libraries, etc.)
• Live & on-demand video content: Oversee a continuous slate of short and long-form video tutorials, live guest-led workshops, and weekly office hours
• AI systems & agents: Work with Product Team to develop and design system prompts for Stack’s AI consulting co-pilot, Stacey
• A content engineer: You balance high standards with high leverage, shipping content that’s quality by default and efficient by design
• An experienced operator: You’ve been in the arena and know firsthand what it takes to turn an idea into a working business
• An AI power user: You don’t just follow AI updates — you test them, use them, and know when they matter
• A systems thinker: You see patterns early, simplify complexity, and turn one-off work into repeatable processes
• Experience creating across formats and audiences, with a strong sense for how medium, context, and message fit together
• A track record of success building and scaling a brand across channels (for yourself, employers, and/or clients)
• A strong grasp of brand as a system — voice, visuals, and behavior working together•
• A point of view on design, and the vocabulary to communicate it
• Elite writing skills and editorial instincts
• A broad scope to own and improve
• Direct impact on every part of the business: product, brand, growth, etc.
• Real autonomy and the freedom to define the role in your likeness
• Access to any AI tool to power your work
A high-throughput, low-ego, fully-remote team that values and rewards great work
Why would you be an amazing fit for Stack?
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