Chief of Staff

The AI Education Project

2d•$150,000 - $175,000•Remote

About The Position

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.

Requirements

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
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

Nice To Haves

experience at a nonprofit or mission-driven organization is a plus

Responsibilities

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
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
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