Chief of Staff & Director of Special Projects Aiedu

Skills / Requirements

• AI Fluency
• AI Workflows
• Analytics Infrastructure
• Content Development
• Dashboard Building
• Discretion
• Education Equity
• Fast-paced Execution
• High EQ
• Leadership Representation
• Media Relations
• Nonprofit Experience
• Ownership Mentality
• Problem Solving
• Project Management
• Stakeholder Management
• Strategic Communication
• Vibe Coding

Why Apply

This role is ideal for someone skilled in building AI-powered tools and workflows, as it involves vibe-coding internal apps and setting up AI workflows to enhance productivity. The position requires fluency with AI tools to create nimble and efficient systems.

What You'll Be Doing

You'll manage the CEO's office, coordinate strategic communications, and act as a proxy in high-stakes situations. You'll also lead special projects, develop AI-powered tools, and oversee marketing and communications initiatives. Travel up to 40% within the U.S. is required.

Pay and Career Growth

The role offers a competitive salary between $150,000 and $175,000, with comprehensive benefits including health insurance, flexible work hours, and a 401k match. The position provides opportunities to influence strategic decisions and grow within a mission-driven organization.

Benefits and Perks

• 401(k) match
• Dental Insurance
• Disability Insurance
• Flexible location
• Flexible work hours
• Health Insurance
• Home Office Stipend
• Life Insurance
• Paid Time Off
• Parental Leave
• Professional Development
• Vision Insurance

Is This Role Right for You?

Original Job Description

About aiEDU

The AI Education Project (aiEDU) is a growing 501(c)(3) non-profit that creates equitable educational experiences to excite and empower learners everywhere with AI literacy. We educate students—especially those disproportionately impacted by artificial intelligence and automation—with the conceptual knowledge and skills they need to thrive as future workers, creators, consumers, and citizens. Join us to make a difference in education and help shape a brighter future for today’s and tomorrow’s learners.

About the role:

The Chief of Staff to the CEO is a high-leverage, high-trust role critical to furthering aiEDU’s growth and impact. You will be the CEO’s closest thought partner and force multiplier—extending his reach, sharpening his voice, and owning the work that shapes how aiEDU shows up to the world.

This is a deliberately blended role built for a communicator with the instincts of an operator. You write with range and precision and can think in another leader’s voice. You read people, rooms, and stakeholders accurately, and you handle sensitive situations with discretion. And you work well with ambiguity, moving from a half-formed idea to a shipped result without waiting for each step to be handed to you.

You’ll also own aiEDU’s communications and marketing function, act as a proxy for the CEO across high-stakes relationships, and lead ambiguous special projects that don’t yet belong to any single team. The through-line here is judgment: knowing what the CEO would say, what a stakeholder needs to hear, which fire to put out first, and when to act without being asked.

⭐ Role Details

Location: This full-time, exempt position can be done on a flexible schedule remotely from anywhere in the U.S. with access to high speed internet, with a preference for someone who can work PST hours. The candidate should be comfortable and equipped to work efficiently in a remote work environment. Up to 40% travel within the U.S. will be required for this role.

Compensation: The baseline compensation range for this role is $150,000-$175,000 depending on experience.

Benefits: We offer a comprehensive benefits package, including full health, dental, and vision for you and any dependents, plus life insurance, short-term and long-term disability insurance, flexible work hours and location, flexible paid time off, paid parental leave, a generous annual stipend for home office expenses and professional development, and a 401k match of 4% vested immediately. For more details regarding our benefits, visit: aiedu.org/careers

Start date: We’d like a candidate to start as soon as possible after receiving an offer, though there is some flexibility.

✅ Your Responsibilities:

Office of the CEO Management

Run the office of the CEO, coordinating the CEO’s focus and priorities in alignment with organizational needs

Provide strategic external communications support — triage incoming communications, draft responses, and ensure timely follow up

Field and triage meeting requests on behalf of the CEO, taking meetings independently where appropriate and preparing briefings and materials for high-stakes engagements

Act as a proxy for the CEO in decision-making and follow-ups, owning next steps and making sure nothing falls through the cracks

Partner with the CEO’s EA on scheduling, travel, expenses and inbox management, and optimize travel time for maximum relationship-building across external partners, programs teams, and funders

Communications & Marketing

Lead and own executive communications for the CEO, including the development and stewardship of thought leadership content via Substack, LinkedIn, and other channels, as well as aiEDU Studios (podcast) 

Lead and own CEO and executive media relations, coordinating with Comms Lead to respond to inbound and regularly engage proactively with journalists

Support the development of presentations and workshop facilitation materials, ensuring the CEO shows up polished and on-message

Manage the Lead, Communications, who is responsible for tactical deployment of aiEDU’s marketing and communications strategy — serving as a strategic thought partner and accountability partner for that person

Build an analytics infrastructure to measure the impact of communications and marketing efforts, and use those insights to inform strategy and future content decisions

Special Projects

Serve as ad-hoc capacity to incubate new initiatives, partnerships, or projects at their earliest stages before handing them off to the appropriate team

Build lightweight, AI-powered tools and workflows that make the Office of the CEO and the comms function faster and more nimble — vibe-coding internal apps and wiring up AI workflows where they remove friction

Lead and advance current in-flight projects, which include vibecoding.aiedu.org and a full aiEDU website revamp

Program manage the aiEDU Advisory Board, organizing meetings, regular updates, and coordinating with other teams to leverage individual advisors across aiEDU workstreams

🚀 About You 

Before reading, please remember that there is no such thing as a “perfect” candidate. If you are on the fence about applying because you are unsure whether you are qualified, we would strongly encourage you to apply. 

You might be a great match for this role if you have:

7+ years of experience in roles that blend strategy, communications, and fast-paced execution — such as Chief of Staff or generalist at a startup or equivalent; experience at a nonprofit or mission-driven organization is a plus

Exceptional written communication skills, with demonstrated ability to write in another leader’s voice and produce compelling content across multiple formats and audiences

High fluency with AI tools, including the ability to build lightweight tools and automations yourself — vibe-coding internal apps, wiring up AI workflows, and standing up systems that make a team faster. You’ve moved beyond just using AI to actually building with it

Strong project management skills and the ability to manage multiple complex workstreams simultaneously without dropping the ball

Analytical mindset with comfort building lightweight dashboards, tracking metrics, and using data to drive decisions

High EQ and strong interpersonal skills; ability to build trust with a wide range of stakeholders and represent leadership with discretion and credibility

A bias toward action and an ownership mentality — you solve problems proactively rather than waiting to be directed

Comfort operating in ambiguity, navigating a fast-paced environment, and wearing multiple hats at once

Passion for equity in education and a genuine belief in aiEDU’s mission

Equal Employment Opportunity

The AI Education Project is an equal opportunity employer. We believe that building and empowering a diverse team is a strategic imperative in our work, and all qualified applicants will receive consideration without regard to race, national origin, age, sex, religion, disability, sexual orientation, marital status, veteran status, gender identity or expression, or any other basis protected by local, state, or federal law.  This policy applies with regard to all aspects of employment, including hiring, promotion, compensation, eligibility for benefits and termination. In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification.